diff --git a/.gitattributes b/.gitattributes index 29330c1944b362e0b57d447b29ed0f491823d265..ca4ab8a2885d83d95dbbf9c985a84b1348242b14 100644 --- a/.gitattributes +++ b/.gitattributes @@ -839,3 +839,5 @@ data/dcoid_decoys.parquet filter=lfs diff=lfs merge=lfs -text data/moad_complex.parquet filter=lfs diff=lfs merge=lfs -text data/pdbbind_complex.parquet filter=lfs diff=lfs merge=lfs -text data/all_maccs.parquet filter=lfs diff=lfs merge=lfs -text +default/binding_affinity-train.parquet filter=lfs diff=lfs merge=lfs -text +default/binding_affinity-no_kras.parquet filter=lfs diff=lfs merge=lfs -text diff --git a/README.md b/README.md deleted file mode 100644 index 2c3b0a70a4043ca7d944ae9b8b3c904e01995c6a..0000000000000000000000000000000000000000 --- a/README.md +++ /dev/null @@ -1,104 +0,0 @@ ---- -tags: -- molecules -- chemistry -- SMILES ---- - -## How to use the data sets - -This dataset contains 1.9M unique pairs of protein sequences and ligand SMILES with experimentally determined -binding affinities. It can be used for fine-tuning a language model. - -The data comes from the following sources: -- BindingDB -- PDBbind-cn -- BioLIP -- BindingMOAD - -### Use the already preprocessed data - -Load a test/train split using - -``` -from datasets import load_dataset -train = load_dataset("jglaser/binding_affinity",split='train[:90%]') -validation = load_dataset("jglaser/binding_affinity",split='train[90%:]') -``` - -Optionally, datasets with certain protein sequences removed are available. -These can be used to test the predictive power for specific proteins even when -these are not part of the training data. - -- `train_no_kras` (no KRAS proteins) - -**Loading the data manually** - -The file `data/all.parquet` contains the preprocessed data. To extract it, -you need download and install [git LFS support] https://git-lfs.github.com/]. - -### Pre-process yourself - -To manually perform the preprocessing, download the data sets from - -1. BindingDB - -In `bindingdb`, download the database as tab separated values - > Download > BindingDB_All_2021m4.tsv.zip -and extract the zip archive into `bindingdb/data` - -Run the steps in `bindingdb.ipynb` - -2. PDBBind-cn - -Register for an account at , confirm the validation -email, then login and download - -- the Index files (1) -- the general protein-ligand complexes (2) -- the refined protein-ligand complexes (3) - -Extract those files in `pdbbind/data` - -Run the script `pdbbind.py` in a compute job on an MPI-enabled cluster -(e.g., `mpirun -n 64 pdbbind.py`). - -Perform the steps in the notebook `pdbbind.ipynb` - -3. BindingMOAD - -Go to and download the files `every.csv` -(All of Binding MOAD, Binding Data) and the non-redundant biounits -(`nr_bind.zip`). Place and extract those files into `binding_moad`. - -Run the script `moad.py` in a compute job on an MPI-enabled cluster -(e.g., `mpirun -n 64 moad.py`). - -Perform the steps in the notebook `moad.ipynb` - -4. BioLIP - -Download from the files -- receptor1.tar.bz2 (Receptor1, Non-redudant set) -- ligand_2013-03-6.tar.bz2 (Ligands) -- BioLiP.tar.bz2 (Annotations) -and extract them in `biolip/data`. - -The following steps are **optional**, they **do not** result in additional binding affinity data. - -Download the script -- download_all_sets.pl -from the Weekly update subpage. - -Update the 2013 database to its current state - -`perl download_all-sets.pl` - -Run the script `biolip.py` in a compute job on an MPI-enabled cluster -(e.g., `mpirun -n 64 biolip.py`). - -Perform the steps in the notebook `biolip.ipynb` - -5. Final concatenation and filtering - -Run the steps in the notebook `combine_dbs.ipynb` diff --git a/binding_affinity.py b/binding_affinity.py deleted file mode 100644 index 616250b3c04187053a9c053826e6ce93c17b18ec..0000000000000000000000000000000000000000 --- a/binding_affinity.py +++ /dev/null @@ -1,147 +0,0 @@ -# coding=utf-8 -# Copyright 2020 The HuggingFace Datasets Authors and the current dataset script contributor. -# -# Licensed under the Apache License, Version 2.0 (the "License"); -# you may not use this file except in compliance with the License. -# You may obtain a copy of the License at -# -# http://www.apache.org/licenses/LICENSE-2.0 -# -# Unless required by applicable law or agreed to in writing, software -# distributed under the License is distributed on an "AS IS" BASIS, -# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. -# See the License for the specific language governing permissions and -# limitations under the License. -"""TODO: A dataset of protein sequences, ligand SMILES and binding affinities.""" - -import huggingface_hub -import os -import pyarrow.parquet as pq -import datasets - - -# TODO: Add BibTeX citation -# Find for instance the citation on arxiv or on the dataset repo/website -_CITATION = """\ -@InProceedings{huggingface:dataset, -title = {jglaser/binding_affinity}, -author={Jens Glaser, ORNL -}, -year={2021} -} -""" - -# TODO: Add description of the dataset here -# You can copy an official description -_DESCRIPTION = """\ -A dataset to fine-tune language models on protein-ligand binding affinity prediction. -""" - -# TODO: Add a link to an official homepage for the dataset here -_HOMEPAGE = "" - -# TODO: Add the licence for the dataset here if you can find it -_LICENSE = "BSD two-clause" - -# TODO: Add link to the official dataset URLs here -# The HuggingFace dataset library don't host the datasets but only point to the original files -# This can be an arbitrary nested dict/list of URLs (see below in `_split_generators` method) -_URL = "https://huggingface.co/datasets/jglaser/binding_affinity/resolve/main/" -_data_dir = "data/" -_file_names = {'default': _data_dir+'all.parquet', - 'no_kras': _data_dir+'all_nokras.parquet', - 'cov': _data_dir+'cov.parquet'} - -_URLs = {name: _URL+_file_names[name] for name in _file_names} - - -# TODO: Name of the dataset usually match the script name with CamelCase instead of snake_case -class BindingAffinity(datasets.ArrowBasedBuilder): - """List of protein sequences, ligand SMILES and binding affinities.""" - - VERSION = datasets.Version("1.4.1") - - def _info(self): - # TODO: This method specifies the datasets.DatasetInfo object which contains informations and typings for the dataset - #if self.config.name == "first_domain": # This is the name of the configuration selected in BUILDER_CONFIGS above - # features = datasets.Features( - # { - # "sentence": datasets.Value("string"), - # "option1": datasets.Value("string"), - # "answer": datasets.Value("string") - # # These are the features of your dataset like images, labels ... - # } - # ) - #else: # This is an example to show how to have different features for "first_domain" and "second_domain" - features = datasets.Features( - { - "seq": datasets.Value("string"), - "smiles": datasets.Value("string"), - "affinity_uM": datasets.Value("float"), - "neg_log10_affinity_M": datasets.Value("float"), - "smiles_can": datasets.Value("string"), - "affinity": datasets.Value("float"), - # These are the features of your dataset like images, labels ... - } - ) - return datasets.DatasetInfo( - # This is the description that will appear on the datasets page. - description=_DESCRIPTION, - # This defines the different columns of the dataset and their types - features=features, # Here we define them above because they are different between the two configurations - # If there's a common (input, target) tuple from the features, - # specify them here. They'll be used if as_supervised=True in - # builder.as_dataset. - supervised_keys=None, - # Homepage of the dataset for documentation - homepage=_HOMEPAGE, - # License for the dataset if available - license=_LICENSE, - # Citation for the dataset - citation=_CITATION, - ) - - def _split_generators(self, dl_manager): - """Returns SplitGenerators.""" - # TODO: This method is tasked with downloading/extracting the data and defining the splits depending on the configuration - # If several configurations are possible (listed in BUILDER_CONFIGS), the configuration selected by the user is in self.config.name - - # dl_manager is a datasets.download.DownloadManager that can be used to download and extract URLs - # It can accept any type or nested list/dict and will give back the same structure with the url replaced with path to local files. - # By default the archives will be extracted and a path to a cached folder where they are extracted is returned instead of the archive - files = dl_manager.download_and_extract(_URLs) - - return [ - datasets.SplitGenerator( - # These kwargs will be passed to _generate_examples - name=datasets.Split.TRAIN, - gen_kwargs={ - 'filepath': files["default"], - }, - ), - - datasets.SplitGenerator( - name='no_kras', - # These kwargs will be passed to _generate_examples - gen_kwargs={ - "filepath": files["no_kras"], - }, - ), - - datasets.SplitGenerator( - name='covalent', - # These kwargs will be passed to _generate_examples - gen_kwargs={ - "filepath": files["cov"], - }, - ), - ] - - def _generate_tables( - self, filepath - ): - from pyarrow import fs - local = fs.LocalFileSystem() - - for i, f in enumerate([filepath]): - yield i, pq.read_table(f,filesystem=local) diff --git a/bindingdb.ipynb b/bindingdb.ipynb deleted file mode 100644 index eda3a39f990a5a9750991ffe600accd8f057d597..0000000000000000000000000000000000000000 --- a/bindingdb.ipynb +++ /dev/null @@ -1,1258 +0,0 @@ -{ - "cells": [ - { - "cell_type": "code", - "execution_count": 2, - "id": "ecce356e-321b-441e-8a5d-a20bf72f8691", - "metadata": {}, - "outputs": [], - "source": [ - "import dask.dataframe as dd" - ] - }, - { - "cell_type": "code", - "execution_count": 3, - "id": "89cbcd82-4ca2-4aba-95b7-e58c0ceed770", - "metadata": {}, - "outputs": [], - "source": [ - "cols = ['Ligand SMILES', 'IC50 (nM)','KEGG ID of Ligand','Ki (nM)', 'Kd (nM)','EC50 (nM)']" - ] - }, - { - "cell_type": "code", - "execution_count": 3, - "id": "a870d8d7-374b-4474-b9ee-305bbf9f17a9", - "metadata": {}, - "outputs": [], - "source": [ - "import tqdm.notebook" - ] - }, - { - "cell_type": "code", - "execution_count": 5, - "id": "e9f76b32-e8f0-47ee-b592-a91a88f4f93e", - "metadata": {}, - "outputs": [ - { - "data": { - "application/vnd.jupyter.widget-view+json": { - "model_id": "c988bc89781242ec8c8b7f8fd0b1c233", - "version_major": 2, - "version_minor": 0 - }, - "text/plain": [ - " 0%| | 0/13 [00:00\n", - "\n", - "\n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - " \n", - "
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" - ], - "text/plain": [ - " Ligand SMILES IC50 (nM) \\\n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 None \n", - "1 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn... None \n", - "2 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=... None \n", - "3 OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@... None \n", - "4 OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H... None \n", - "\n", - " KEGG ID of Ligand Ki (nM) Kd (nM) EC50 (nM) \\\n", - "0 None 0.24 None None \n", - "1 None 0.25 None None \n", - "2 None 0.41 None None \n", - "3 None 0.8 None None \n", - "4 None 0.99 None None \n", - "\n", - " seq \n", - "0 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "1 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "2 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "3 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "4 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... " - ] - }, - "execution_count": 8, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "ddf_nonnull.head()" - ] - }, - { - "cell_type": "code", - "execution_count": 17, - "id": "7b423365-4989-4325-a5a5-845d852d52e9", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2512985" - ] - }, - "execution_count": 17, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(ddf_nonnull)" - ] - }, - { - "cell_type": "code", - "execution_count": 11, - "id": "872edb84-3459-43d9-8e0e-e2a6b5d281eb", - "metadata": {}, - "outputs": [], - "source": [ - "from pint import UnitRegistry\n", - "import numpy as np\n", - "import re\n", - "ureg = UnitRegistry()\n", - "\n", - "def to_uM(affinities):\n", - " ic50, Ki, Kd, ec50 = affinities\n", - "\n", - " vals = []\n", - " \n", - " try:\n", - " ic50 = ureg(str(ic50)+'nM').m_as(ureg.uM)\n", - " vals.append(ic50)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " Ki = ureg(str(Ki)+'nM').m_as(ureg.uM)\n", - " vals.append(Ki)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " Kd = ureg(str(Kd)+'nM').m_as(ureg.uM)\n", - " vals.append(Kd)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " ec50 = ureg(str(ec50)+'nM').m_as(ureg.uM)\n", - " vals.append(ec50)\n", - " except:\n", - " pass\n", - "\n", - " if len(vals) > 0:\n", - " vals = np.array(vals)\n", - " return np.mean(vals[~np.isnan(vals)])\n", - " \n", - " return None" - ] - }, - { - "cell_type": "code", - "execution_count": 12, - "id": "b3cff13c-19b2-4413-a84b-d99062f516a7", - "metadata": {}, - "outputs": [], - "source": [ - "df_nonnull = ddf_nonnull.compute()" - ] - }, - { - "cell_type": "code", - "execution_count": 13, - "id": "ca9795de-e821-4dc3-a7bf-70ade9e4c7f0", - "metadata": {}, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "INFO: Pandarallel will run on 32 workers.\n", - "INFO: Pandarallel will use Memory file system to transfer data between the main process and workers.\n" - ] - } - ], - "source": [ - "from pandarallel import pandarallel\n", - "pandarallel.initialize()\n" - ] - }, - { - "cell_type": "code", - "execution_count": 14, - "id": "4356a3e2-fede-48e7-a486-343661fe0a0a", - "metadata": {}, - "outputs": [], - "source": [ - "df_affinity = df_nonnull.copy()\n", - "df_affinity['affinity_uM'] = df_affinity[['IC50 (nM)', 'Ki (nM)', 'Kd (nM)','EC50 (nM)']].parallel_apply(to_uM,axis=1)" - ] - }, - { - "cell_type": "code", - "execution_count": 15, - "id": "e91c3af8-84a5-42a2-9e25-49cb2f320b0b", - "metadata": {}, - "outputs": [], - "source": [ - "df_affinity[~df_affinity['affinity_uM'].isnull()].to_parquet('data/bindingdb.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 1, - "id": "f3a9173e-d574-4314-9cea-f8c0a66766c0", - "metadata": {}, - "outputs": [], - "source": [ - "import pandas as pd\n", - "df_affinity = pd.read_parquet('data/bindingdb.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 2, - "id": "f602fdbe-7083-436c-9eac-9d97fbc8be67", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2510716" - ] - }, - "execution_count": 2, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_affinity)" - ] - }, - { - "cell_type": "code", - "execution_count": 3, - "id": "27194288-cf3e-4c30-ad55-3b0998fdf939", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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Ligand SMILESIC50 (nM)KEGG ID of LigandKi (nM)Kd (nM)EC50 (nM)seqaffinity_uM
0COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1NoneNone0.24NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00024
1O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn...NoneNone0.25NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00025
2O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=...NoneNone0.41NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00041
3OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@...NoneNone0.8NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00080
4OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H...NoneNone0.99NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00099
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" - ], - "text/plain": [ - " Ligand SMILES IC50 (nM) \\\n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 None \n", - "1 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn... None \n", - "2 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=... None \n", - "3 OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@... None \n", - "4 OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H... None \n", - "\n", - " KEGG ID of Ligand Ki (nM) Kd (nM) EC50 (nM) \\\n", - "0 None 0.24 None None \n", - "1 None 0.25 None None \n", - "2 None 0.41 None None \n", - "3 None 0.8 None None \n", - "4 None 0.99 None None \n", - "\n", - " seq affinity_uM \n", - "0 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00024 \n", - "1 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00025 \n", - "2 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00041 \n", - "3 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00080 \n", - "4 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00099 " - ] - }, - "execution_count": 3, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_affinity.head()" - ] - }, - { - "cell_type": "code", - "execution_count": 4, - "id": "603fd298-0aa6-4097-b298-c55db013548c", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2510716" - ] - }, - "execution_count": 4, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_affinity)" - ] - }, - { - "cell_type": "code", - "execution_count": 5, - "id": "d95ad9a9-d4ca-4679-8a33-235fe6e7047f", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2510716" - ] - }, - "execution_count": 5, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_affinity[~df_affinity['affinity_uM'].isnull()])" - ] - }, - { - "cell_type": "code", - "execution_count": 6, - "id": "b21c4683-0fe1-4a0a-a55c-c0dc80193f36", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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Ligand SMILESIC50 (nM)KEGG ID of LigandKi (nM)Kd (nM)EC50 (nM)seqaffinity_uM
0COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1NoneNone0.24NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00024
1O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn...NoneNone0.25NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00025
2O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=...NoneNone0.41NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00041
3OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@...NoneNone0.8NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00080
4OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H...NoneNone0.99NoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...0.00099
...........................
5112COc1ccc(NC(=O)N2CCC(CC2)C(=O)N[C@@H](CC(C)C)C(...17NoneNoneNoneNoneMSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE...0.01700
5113CC(C)C[C@H](NC(=O)C1CCN(CC1)C(=O)Nc1cnccn1)C(=...76NoneNoneNoneNoneMSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE...0.07600
5313C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)...>100000NoneNoneNoneNoneMSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE...100.00000
5314FCC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)c1cccc2ccc...>100000NoneNoneNoneNoneMSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE...100.00000
5361FCC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1>100000NoneNoneNoneNoneMSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE...100.00000
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2510716 rows × 8 columns

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" - ], - "text/plain": [ - " Ligand SMILES IC50 (nM) \\\n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 None \n", - "1 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn... None \n", - "2 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=... None \n", - "3 OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@... None \n", - "4 OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H... None \n", - "... ... ... \n", - "5112 COc1ccc(NC(=O)N2CCC(CC2)C(=O)N[C@@H](CC(C)C)C(... 17 \n", - "5113 CC(C)C[C@H](NC(=O)C1CCN(CC1)C(=O)Nc1cnccn1)C(=... 76 \n", - "5313 C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)... >100000 \n", - "5314 FCC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)c1cccc2ccc... >100000 \n", - "5361 FCC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1 >100000 \n", - "\n", - " KEGG ID of Ligand Ki (nM) Kd (nM) EC50 (nM) \\\n", - "0 None 0.24 None None \n", - "1 None 0.25 None None \n", - "2 None 0.41 None None \n", - "3 None 0.8 None None \n", - "4 None 0.99 None None \n", - "... ... ... ... ... \n", - "5112 None None None None \n", - "5113 None None None None \n", - "5313 None None None None \n", - "5314 None None None None \n", - "5361 None None None None \n", - "\n", - " seq affinity_uM \n", - "0 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00024 \n", - "1 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00025 \n", - "2 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00041 \n", - "3 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00080 \n", - "4 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... 0.00099 \n", - "... ... ... \n", - "5112 MSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE... 0.01700 \n", - "5113 MSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE... 0.07600 \n", - "5313 MSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE... 100.00000 \n", - "5314 MSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE... 100.00000 \n", - "5361 MSYDRAITVFSPDGHLFQVEYAQEAVKKGSTAVGVRGRDIVVLGVE... 100.00000 \n", - "\n", - "[2510716 rows x 8 columns]" - ] - }, - "execution_count": 6, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_affinity" - ] - }, - { - "cell_type": "code", - "execution_count": 25, - "id": "20690729", - "metadata": {}, - "outputs": [], - "source": [ - "import rdkit.Chem as Chem" - ] - }, - { - "cell_type": "code", - "execution_count": 27, - "id": "48114dcc", - "metadata": {}, - "outputs": [], - "source": [ - "df_pdb = df[~df['PDB ID(s) for Ligand-Target Complex'].isnull()][['PDB ID(s) for Ligand-Target Complex','Ligand SMILES']]" - ] - }, - { - "cell_type": "code", - "execution_count": 28, - "id": "caa0497c", - "metadata": {}, - "outputs": [], - "source": [ - "def make_canonical(smi):\n", - " return Chem.MolToSmiles(Chem.MolFromSmiles(smi))\n", - "\n", - "df_pdb['can_smiles'] = df_pdb['Ligand SMILES'].apply(make_canonical)" - ] - }, - { - "cell_type": "code", - "execution_count": 29, - "id": "e82d64f3", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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PDB ID(s) for Ligand-Target ComplexLigand SMILEScan_smiles
02IVUCOc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1
291HWRO[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC=C)C(=O)...C=CCN1C(=O)N(CC=C)[C@H](Cc2ccccc2)[C@H](O)[C@@...
346DGY,6DH1,6DH4,6DH7,3O99CC[C@H](C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O...CC[C@H](C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O...
1291MES,1MEU,1MET,1BVG,1BVE,3JVW,1QBSOCc1ccc(CN2[C@H](Cc3ccccc3)[C@H](O)[C@@H](O)[C...O=C1N(Cc2ccc(CO)cc2)[C@H](Cc2ccccc2)[C@H](O)[C...
1301MER,1DMP,1RQ9Nc1cccc(CN2[C@H](Cc3ccccc3)[C@H](O)[C@@H](O)[C...Nc1cccc(CN2C(=O)N(Cc3cccc(N)c3)[C@H](Cc3ccccc3...
............
23333751MUI,2RKG,2RKF,1RV7,2Q5K,2O4S,6DJ1,6DJ2,3OGQ,2...CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@...Cc1cccc(C)c1OCC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)...
23333764NPT,4DQH,4DQE,5E5J,3JW2,6OPU,6OPX,2HS2,2HS1,2...CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]...CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]...
23333806EKZ,1DY4,5FUK,6PS5CC(C)NCC(O)COc1cccc2ccccc12CC(C)NCC(O)COc1cccc2ccccc12
23333846EKZ,1DY4,5FUK,6PS5CC(C)NCC(O)COc1cccc2ccccc12CC(C)NCC(O)COc1cccc2ccccc12
23333856A60,3DCTCC(C)c1onc(c1COc1ccc(\\C=C\\c2cccc(c2)C(O)=O)c(C...CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc(/C=C/c2cc...
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123385 rows × 3 columns

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" - ], - "text/plain": [ - " PDB ID(s) for Ligand-Target Complex \\\n", - "0 2IVU \n", - "29 1HWR \n", - "34 6DGY,6DH1,6DH4,6DH7,3O99 \n", - "129 1MES,1MEU,1MET,1BVG,1BVE,3JVW,1QBS \n", - "130 1MER,1DMP,1RQ9 \n", - "... ... \n", - "2333375 1MUI,2RKG,2RKF,1RV7,2Q5K,2O4S,6DJ1,6DJ2,3OGQ,2... \n", - "2333376 4NPT,4DQH,4DQE,5E5J,3JW2,6OPU,6OPX,2HS2,2HS1,2... \n", - "2333380 6EKZ,1DY4,5FUK,6PS5 \n", - "2333384 6EKZ,1DY4,5FUK,6PS5 \n", - "2333385 6A60,3DCT \n", - "\n", - " Ligand SMILES \\\n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 \n", - "29 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC=C)C(=O)... \n", - "34 CC[C@H](C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O... \n", - "129 OCc1ccc(CN2[C@H](Cc3ccccc3)[C@H](O)[C@@H](O)[C... \n", - "130 Nc1cccc(CN2[C@H](Cc3ccccc3)[C@H](O)[C@@H](O)[C... \n", - "... ... \n", - "2333375 CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@... \n", - "2333376 CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]... \n", - "2333380 CC(C)NCC(O)COc1cccc2ccccc12 \n", - "2333384 CC(C)NCC(O)COc1cccc2ccccc12 \n", - "2333385 CC(C)c1onc(c1COc1ccc(\\C=C\\c2cccc(c2)C(O)=O)c(C... \n", - "\n", - " can_smiles \n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 \n", - "29 C=CCN1C(=O)N(CC=C)[C@H](Cc2ccccc2)[C@H](O)[C@@... \n", - "34 CC[C@H](C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O... \n", - "129 O=C1N(Cc2ccc(CO)cc2)[C@H](Cc2ccccc2)[C@H](O)[C... \n", - "130 Nc1cccc(CN2C(=O)N(Cc3cccc(N)c3)[C@H](Cc3ccccc3... \n", - "... ... \n", - "2333375 Cc1cccc(C)c1OCC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)... \n", - "2333376 CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]... \n", - "2333380 CC(C)NCC(O)COc1cccc2ccccc12 \n", - "2333384 CC(C)NCC(O)COc1cccc2ccccc12 \n", - "2333385 CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc(/C=C/c2cc... \n", - "\n", - "[123385 rows x 3 columns]" - ] - }, - "execution_count": 29, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_pdb" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "593c9aec", - "metadata": {}, - "outputs": [], - "source": [] - } - ], - "metadata": { - "kernelspec": { - "display_name": "Python 3", - "language": "python", - "name": "python3" - }, - "language_info": { - "codemirror_mode": { - "name": "ipython", - "version": 3 - }, - "file_extension": ".py", - "mimetype": "text/x-python", - "name": "python", - "nbconvert_exporter": "python", - "pygments_lexer": "ipython3", - "version": "3.9.4" - } - }, - "nbformat": 4, - "nbformat_minor": 5 -} diff --git a/bindingdb_single.ipynb b/bindingdb_single.ipynb deleted file mode 100644 index 0c34fcc0c52f0d575ab0e9ca1718c8ec796df8ef..0000000000000000000000000000000000000000 --- a/bindingdb_single.ipynb +++ /dev/null @@ -1,1036 +0,0 @@ -{ - "cells": [ - { - "cell_type": "code", - "execution_count": 1, - "id": "ecce356e-321b-441e-8a5d-a20bf72f8691", - "metadata": {}, - "outputs": [], - "source": [ - "import pandas as pd\n", - "import dask.dataframe as dd" - ] - }, - { - "cell_type": "code", - "execution_count": 2, - "id": "89cbcd82-4ca2-4aba-95b7-e58c0ceed770", - "metadata": {}, - "outputs": [], - "source": [ - "cols = ['Ligand SMILES', 'IC50 (nM)','KEGG ID of Ligand','Ki (nM)', 'Kd (nM)','EC50 (nM)']" - ] - }, - { - "cell_type": "code", - "execution_count": 3, - "id": "1b923f02-e858-4737-ab5e-4c98c2def1b6", - "metadata": {}, - "outputs": [], - "source": [ - "allseq = ['BindingDB Target Chain Sequence']+['BindingDB Target Chain Sequence.{}'.format(j) for j in range(1,13)]" - ] - }, - { - "cell_type": "code", - "execution_count": 4, - "id": "54f0721e-1e36-48cc-a635-a1617a04f9e5", - "metadata": {}, - "outputs": [], - "source": [ - "dtypes = {'BindingDB Target Chain Sequence.{}'.format(i): 'object' for i in range(1,13)}" - ] - }, - { - "cell_type": "code", - "execution_count": 5, - "id": "c1843c65-a5ef-4604-adca-40fb18bc2991", - "metadata": {}, - "outputs": [], - "source": [ - "dtypes.update({'BindingDB Target Chain Sequence': 'object',\n", - " 'IC50 (nM)': 'object',\n", - " 'KEGG ID of Ligand': 'object',\n", - " 'Ki (nM)': 'object',\n", - " 'Kd (nM)': 'object',\n", - " 'EC50 (nM)': 'object',\n", - " 'koff (s-1)': 'object'})" - ] - }, - { - "cell_type": "code", - "execution_count": 6, - "id": "aa337ac3-4ca1-4369-a9c7-ab705221a137", - "metadata": {}, - "outputs": [], - "source": [ - "seq_name = 'BindingDB Target Chain Sequence'" - ] - }, - { - "cell_type": "code", - "execution_count": 7, - "id": "a870d8d7-374b-4474-b9ee-305bbf9f17a9", - "metadata": {}, - "outputs": [], - "source": [ - "import tqdm.notebook" - ] - }, - { - "cell_type": "code", - "execution_count": 8, - "id": "e97d29e6-d153-480e-a1ee-c216c22af8d2", - "metadata": {}, - "outputs": [], - "source": [ - "ddf = dd.read_csv('bindingdb/data/BindingDB_All.tsv',sep='\\t',\n", - " error_bad_lines=False,\n", - " usecols=cols+allseq,\n", - " dtype=dtypes)" - ] - }, - { - "cell_type": "code", - "execution_count": 11, - "id": "a4b381c0-968b-4248-a24f-9609acb12136", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "0.04789522637942933" - ] - }, - "execution_count": 11, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(ddf[~ddf['BindingDB Target Chain Sequence.1'].isnull()])/len(ddf[~ddf['BindingDB Target Chain Sequence'].isnull()])" - ] - }, - { - "cell_type": "code", - "execution_count": 18, - "id": "7a8efd3f-c9c4-4f6a-83e5-9e9610deb17f", - "metadata": {}, - "outputs": [], - "source": [ - "# remove rows with more than one target\n", - "ddf_prune = ddf[ddf['BindingDB Target Chain Sequence.1'].isnull()]\n", - "ddf_prune = ddf_prune.rename(columns={'BindingDB Target Chain Sequence': 'seq'})" - ] - }, - { - "cell_type": "code", - "execution_count": 19, - "id": "c00102b8-f4be-4ebd-8d30-7a2c7fc2d05e", - "metadata": {}, - "outputs": [], - "source": [ - "ddf_nonnull = ddf_prune[~ddf_prune.seq.isnull()].copy()" - ] - }, - { - "cell_type": "code", - "execution_count": 20, - "id": "c5337e06-1e45-4180-90ed-49ac9ecdd24a", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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Ligand SMILESKi (nM)IC50 (nM)Kd (nM)EC50 (nM)KEGG ID of LigandseqBindingDB Target Chain Sequence.1BindingDB Target Chain Sequence.2BindingDB Target Chain Sequence.3BindingDB Target Chain Sequence.4BindingDB Target Chain Sequence.5BindingDB Target Chain Sequence.6BindingDB Target Chain Sequence.7BindingDB Target Chain Sequence.8BindingDB Target Chain Sequence.9BindingDB Target Chain Sequence.10BindingDB Target Chain Sequence.11BindingDB Target Chain Sequence.12
0COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC10.24NaNNaNNaNNaNPQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...NaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaN
1O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn...0.25NaNNaNNaNNaNPQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...NaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaN
2O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=...0.41NaNNaNNaNNaNPQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...NaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaN
3OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@...0.8NaNNaNNaNNaNPQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...NaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaN
4OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H...0.99NaNNaNNaNNaNPQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...NaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaNNaN
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" - ], - "text/plain": [ - " Ligand SMILES Ki (nM) IC50 (nM) \\\n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 0.24 NaN \n", - "1 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn... 0.25 NaN \n", - "2 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=... 0.41 NaN \n", - "3 OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@... 0.8 NaN \n", - "4 OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H... 0.99 NaN \n", - "\n", - " Kd (nM) EC50 (nM) KEGG ID of Ligand \\\n", - "0 NaN NaN NaN \n", - "1 NaN NaN NaN \n", - "2 NaN NaN NaN \n", - "3 NaN NaN NaN \n", - "4 NaN NaN NaN \n", - "\n", - " seq \\\n", - "0 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "1 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "2 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "3 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "4 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "\n", - " BindingDB Target Chain Sequence.1 BindingDB Target Chain Sequence.2 \\\n", - "0 NaN NaN \n", - "1 NaN NaN \n", - "2 NaN NaN \n", - "3 NaN NaN \n", - "4 NaN NaN \n", - "\n", - " BindingDB Target Chain Sequence.3 BindingDB Target Chain Sequence.4 \\\n", - "0 NaN NaN \n", - "1 NaN NaN \n", - "2 NaN NaN \n", - "3 NaN NaN \n", - "4 NaN NaN \n", - "\n", - " BindingDB Target Chain Sequence.5 BindingDB Target Chain Sequence.6 \\\n", - "0 NaN NaN \n", - "1 NaN NaN \n", - "2 NaN NaN \n", - "3 NaN NaN \n", - "4 NaN NaN \n", - "\n", - " BindingDB Target Chain Sequence.7 BindingDB Target Chain Sequence.8 \\\n", - "0 NaN NaN \n", - "1 NaN NaN \n", - "2 NaN NaN \n", - "3 NaN NaN \n", - "4 NaN NaN \n", - "\n", - " BindingDB Target Chain Sequence.9 BindingDB Target Chain Sequence.10 \\\n", - "0 NaN NaN \n", - "1 NaN NaN \n", - "2 NaN NaN \n", - "3 NaN NaN \n", - "4 NaN NaN \n", - "\n", - " BindingDB Target Chain Sequence.11 BindingDB Target Chain Sequence.12 \n", - "0 NaN NaN \n", - "1 NaN NaN \n", - "2 NaN NaN \n", - "3 NaN NaN \n", - "4 NaN NaN " - ] - }, - "execution_count": 20, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "ddf_nonnull.head()" - ] - }, - { - "cell_type": "code", - "execution_count": 21, - "id": "7b423365-4989-4325-a5a5-845d852d52e9", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2221761" - ] - }, - "execution_count": 21, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(ddf_nonnull)" - ] - }, - { - "cell_type": "code", - "execution_count": 22, - "id": "872edb84-3459-43d9-8e0e-e2a6b5d281eb", - "metadata": {}, - "outputs": [], - "source": [ - "from pint import UnitRegistry\n", - "import numpy as np\n", - "import re\n", - "ureg = UnitRegistry()\n", - "\n", - "def to_uM(affinities):\n", - " ic50, Ki, Kd, ec50 = affinities\n", - "\n", - " vals = []\n", - " \n", - " try:\n", - " ic50 = ureg(str(ic50)+'nM').m_as(ureg.uM)\n", - " vals.append(ic50)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " Ki = ureg(str(Ki)+'nM').m_as(ureg.uM)\n", - " vals.append(Ki)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " Kd = ureg(str(Kd)+'nM').m_as(ureg.uM)\n", - " vals.append(Kd)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " ec50 = ureg(str(ec50)+'nM').m_as(ureg.uM)\n", - " vals.append(ec50)\n", - " except:\n", - " pass\n", - "\n", - " if len(vals) > 0:\n", - " vals = np.array(vals)\n", - " return np.mean(vals[~np.isnan(vals)])\n", - " \n", - " return None" - ] - }, - { - "cell_type": "code", - "execution_count": 23, - "id": "b3cff13c-19b2-4413-a84b-d99062f516a7", - "metadata": {}, - "outputs": [], - "source": [ - "df_nonnull = ddf_nonnull.compute()" - ] - }, - { - "cell_type": "code", - "execution_count": 24, - "id": "ca9795de-e821-4dc3-a7bf-70ade9e4c7f0", - "metadata": {}, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "INFO: Pandarallel will run on 32 workers.\n", - "INFO: Pandarallel will use Memory file system to transfer data between the main process and workers.\n" - ] - } - ], - "source": [ - "from pandarallel import pandarallel\n", - "pandarallel.initialize()\n" - ] - }, - { - "cell_type": "code", - "execution_count": 25, - "id": "4356a3e2-fede-48e7-a486-343661fe0a0a", - "metadata": {}, - "outputs": [], - "source": [ - "df_affinity = df_nonnull.copy()\n", - "df_affinity['affinity_uM'] = df_affinity[['IC50 (nM)', 'Ki (nM)', 'Kd (nM)','EC50 (nM)']].parallel_apply(to_uM,axis=1)" - ] - }, - { - "cell_type": "code", - "execution_count": 26, - "id": "e91c3af8-84a5-42a2-9e25-49cb2f320b0b", - "metadata": {}, - "outputs": [], - "source": [ - "df_affinity[~df_affinity['affinity_uM'].isnull()].to_parquet('data/bindingdb.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 27, - "id": "f3a9173e-d574-4314-9cea-f8c0a66766c0", - "metadata": {}, - "outputs": [], - "source": [ - "import pandas as pd\n", - "df_affinity = pd.read_parquet('data/bindingdb.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 28, - "id": "f602fdbe-7083-436c-9eac-9d97fbc8be67", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2219812" - ] - }, - "execution_count": 28, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_affinity)" - ] - }, - { - "cell_type": "code", - "execution_count": 29, - "id": "27194288-cf3e-4c30-ad55-3b0998fdf939", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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Ligand SMILESKi (nM)IC50 (nM)Kd (nM)EC50 (nM)KEGG ID of LigandseqBindingDB Target Chain Sequence.1BindingDB Target Chain Sequence.2BindingDB Target Chain Sequence.3BindingDB Target Chain Sequence.4BindingDB Target Chain Sequence.5BindingDB Target Chain Sequence.6BindingDB Target Chain Sequence.7BindingDB Target Chain Sequence.8BindingDB Target Chain Sequence.9BindingDB Target Chain Sequence.10BindingDB Target Chain Sequence.11BindingDB Target Chain Sequence.12affinity_uM
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1O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn...0.25NoneNoneNoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...NoneNoneNoneNoneNoneNoneNoneNoneNoneNoneNoneNone0.00025
2O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=...0.41NoneNoneNoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...NoneNoneNoneNoneNoneNoneNoneNoneNoneNoneNoneNone0.00041
3OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@...0.8NoneNoneNoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...NoneNoneNoneNoneNoneNoneNoneNoneNoneNoneNoneNone0.00080
4OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H...0.99NoneNoneNoneNonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...NoneNoneNoneNoneNoneNoneNoneNoneNoneNoneNoneNone0.00099
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" - ], - "text/plain": [ - " Ligand SMILES Ki (nM) IC50 (nM) \\\n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 0.24 None \n", - "1 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn... 0.25 None \n", - "2 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=... 0.41 None \n", - "3 OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@... 0.8 None \n", - "4 OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H... 0.99 None \n", - "\n", - " Kd (nM) EC50 (nM) KEGG ID of Ligand \\\n", - "0 None None None \n", - "1 None None None \n", - "2 None None None \n", - "3 None None None \n", - "4 None None None \n", - "\n", - " seq \\\n", - "0 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "1 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "2 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "3 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "4 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "\n", - " BindingDB Target Chain Sequence.1 BindingDB Target Chain Sequence.2 \\\n", - "0 None None \n", - "1 None None \n", - "2 None None \n", - "3 None None \n", - "4 None None \n", - "\n", - " BindingDB Target Chain Sequence.3 BindingDB Target Chain Sequence.4 \\\n", - "0 None None \n", - "1 None None \n", - "2 None None \n", - "3 None None \n", - "4 None None \n", - "\n", - " BindingDB Target Chain Sequence.5 BindingDB Target Chain Sequence.6 \\\n", - "0 None None \n", - "1 None None \n", - "2 None None \n", - "3 None None \n", - "4 None None \n", - "\n", - " BindingDB Target Chain Sequence.7 BindingDB Target Chain Sequence.8 \\\n", - "0 None None \n", - "1 None None \n", - "2 None None \n", - "3 None None \n", - "4 None None \n", - "\n", - " BindingDB Target Chain Sequence.9 BindingDB Target Chain Sequence.10 \\\n", - "0 None None \n", - "1 None None \n", - "2 None None \n", - "3 None None \n", - "4 None None \n", - "\n", - " BindingDB Target Chain Sequence.11 BindingDB Target Chain Sequence.12 \\\n", - "0 None None \n", - "1 None None \n", - "2 None None \n", - "3 None None \n", - "4 None None \n", - "\n", - " affinity_uM \n", - "0 0.00024 \n", - "1 0.00025 \n", - "2 0.00041 \n", - "3 0.00080 \n", - "4 0.00099 " - ] - }, - "execution_count": 29, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_affinity.head()" - ] - }, - { - "cell_type": "code", - "execution_count": 30, - "id": "603fd298-0aa6-4097-b298-c55db013548c", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2219812" - ] - }, - "execution_count": 30, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_affinity)" - ] - }, - { - "cell_type": "code", - "execution_count": 31, - "id": "d95ad9a9-d4ca-4679-8a33-235fe6e7047f", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2219812" - ] - }, - "execution_count": 31, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_affinity[~df_affinity['affinity_uM'].isnull()])" - ] - }, - { - "cell_type": "code", - "execution_count": 25, - "id": "20690729", - "metadata": {}, - "outputs": [], - "source": [ - "import rdkit.Chem as Chem" - ] - }, - { - "cell_type": "code", - "execution_count": 27, - "id": "48114dcc", - "metadata": {}, - "outputs": [], - "source": [ - "df_pdb = df[~df['PDB ID(s) for Ligand-Target Complex'].isnull()][['PDB ID(s) for Ligand-Target Complex','Ligand SMILES']]" - ] - }, - { - "cell_type": "code", - "execution_count": 28, - "id": "caa0497c", - "metadata": {}, - "outputs": [], - "source": [ - "def make_canonical(smi):\n", - " return Chem.MolToSmiles(Chem.MolFromSmiles(smi))\n", - "\n", - "df_pdb['can_smiles'] = df_pdb['Ligand SMILES'].apply(make_canonical)" - ] - }, - { - "cell_type": "code", - "execution_count": 29, - "id": "e82d64f3", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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PDB ID(s) for Ligand-Target ComplexLigand SMILEScan_smiles
02IVUCOc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1
291HWRO[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC=C)C(=O)...C=CCN1C(=O)N(CC=C)[C@H](Cc2ccccc2)[C@H](O)[C@@...
346DGY,6DH1,6DH4,6DH7,3O99CC[C@H](C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O...CC[C@H](C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O...
1291MES,1MEU,1MET,1BVG,1BVE,3JVW,1QBSOCc1ccc(CN2[C@H](Cc3ccccc3)[C@H](O)[C@@H](O)[C...O=C1N(Cc2ccc(CO)cc2)[C@H](Cc2ccccc2)[C@H](O)[C...
1301MER,1DMP,1RQ9Nc1cccc(CN2[C@H](Cc3ccccc3)[C@H](O)[C@@H](O)[C...Nc1cccc(CN2C(=O)N(Cc3cccc(N)c3)[C@H](Cc3ccccc3...
............
23333751MUI,2RKG,2RKF,1RV7,2Q5K,2O4S,6DJ1,6DJ2,3OGQ,2...CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@...Cc1cccc(C)c1OCC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)...
23333764NPT,4DQH,4DQE,5E5J,3JW2,6OPU,6OPX,2HS2,2HS1,2...CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]...CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]...
23333806EKZ,1DY4,5FUK,6PS5CC(C)NCC(O)COc1cccc2ccccc12CC(C)NCC(O)COc1cccc2ccccc12
23333846EKZ,1DY4,5FUK,6PS5CC(C)NCC(O)COc1cccc2ccccc12CC(C)NCC(O)COc1cccc2ccccc12
23333856A60,3DCTCC(C)c1onc(c1COc1ccc(\\C=C\\c2cccc(c2)C(O)=O)c(C...CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc(/C=C/c2cc...
\n", - "

123385 rows × 3 columns

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" - ], - "text/plain": [ - " PDB ID(s) for Ligand-Target Complex \\\n", - "0 2IVU \n", - "29 1HWR \n", - "34 6DGY,6DH1,6DH4,6DH7,3O99 \n", - "129 1MES,1MEU,1MET,1BVG,1BVE,3JVW,1QBS \n", - "130 1MER,1DMP,1RQ9 \n", - "... ... \n", - "2333375 1MUI,2RKG,2RKF,1RV7,2Q5K,2O4S,6DJ1,6DJ2,3OGQ,2... \n", - "2333376 4NPT,4DQH,4DQE,5E5J,3JW2,6OPU,6OPX,2HS2,2HS1,2... \n", - "2333380 6EKZ,1DY4,5FUK,6PS5 \n", - "2333384 6EKZ,1DY4,5FUK,6PS5 \n", - "2333385 6A60,3DCT \n", - "\n", - " Ligand SMILES \\\n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 \n", - "29 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC=C)C(=O)... \n", - "34 CC[C@H](C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O... \n", - "129 OCc1ccc(CN2[C@H](Cc3ccccc3)[C@H](O)[C@@H](O)[C... \n", - "130 Nc1cccc(CN2[C@H](Cc3ccccc3)[C@H](O)[C@@H](O)[C... \n", - "... ... \n", - "2333375 CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@... \n", - "2333376 CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]... \n", - "2333380 CC(C)NCC(O)COc1cccc2ccccc12 \n", - "2333384 CC(C)NCC(O)COc1cccc2ccccc12 \n", - "2333385 CC(C)c1onc(c1COc1ccc(\\C=C\\c2cccc(c2)C(O)=O)c(C... \n", - "\n", - " can_smiles \n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 \n", - "29 C=CCN1C(=O)N(CC=C)[C@H](Cc2ccccc2)[C@H](O)[C@@... \n", - "34 CC[C@H](C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O... \n", - "129 O=C1N(Cc2ccc(CO)cc2)[C@H](Cc2ccccc2)[C@H](O)[C... \n", - "130 Nc1cccc(CN2C(=O)N(Cc3cccc(N)c3)[C@H](Cc3ccccc3... \n", - "... ... \n", - "2333375 Cc1cccc(C)c1OCC(=O)N[C@@H](Cc1ccccc1)[C@@H](O)... \n", - "2333376 CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]... \n", - "2333380 CC(C)NCC(O)COc1cccc2ccccc12 \n", - "2333384 CC(C)NCC(O)COc1cccc2ccccc12 \n", - "2333385 CC(C)c1onc(-c2c(Cl)cccc2Cl)c1COc1ccc(/C=C/c2cc... \n", - "\n", - "[123385 rows x 3 columns]" - ] - }, - "execution_count": 29, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_pdb" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "593c9aec", - "metadata": {}, - "outputs": [], - "source": [] - } - ], - "metadata": { - "kernelspec": { - "display_name": "Python 3", - "language": "python", - "name": "python3" - }, - "language_info": { - "codemirror_mode": { - "name": "ipython", - "version": 3 - }, - "file_extension": ".py", - "mimetype": "text/x-python", - "name": "python", - "nbconvert_exporter": "python", - "pygments_lexer": "ipython3", - "version": "3.9.4" - } - }, - "nbformat": 4, - "nbformat_minor": 5 -} diff --git a/biolip.ipynb b/biolip.ipynb deleted file mode 100644 index 9aa88ed2db1459e7f645e4c63c8bc0ca08cf2b24..0000000000000000000000000000000000000000 --- a/biolip.ipynb +++ /dev/null @@ -1,586 +0,0 @@ -{ - "cells": [ - { - "cell_type": "code", - "execution_count": 3, - "id": "26bc18a2-a6eb-49d3-be80-876ddc7dd8e1", - "metadata": {}, - "outputs": [], - "source": [ - "import pandas as pd" - ] - }, - { - "cell_type": "markdown", - "id": "dbef8a5d-8603-4f40-aa98-fe50aa1160f6", - "metadata": {}, - "source": [ - "the binding affinities are **only** present in the 2013 snapshot, not in the updated ones" - ] - }, - { - "cell_type": "code", - "execution_count": 48, - "id": "3b59cfb4-c42a-425d-9653-44f07f9e864e", - "metadata": {}, - "outputs": [], - "source": [ - "df = pd.read_table('biolip/data/BioLiP_2013-03-6_nr.txt',sep='\\t',header=None,usecols=[0,4,5,6,13,14,15,16,19])\n", - "df = df.rename(columns={0:'pdb',4:'chain',5:'l_id',6:'l_chain',\n", - " 13: 'affinity_lit',14: 'affinity_moad',15: 'affinity_pdbbind-cn',16:'affinity_bindingdb',\n", - " 19: 'seq'})" - ] - }, - { - "cell_type": "code", - "execution_count": 49, - "id": "01123edd-2b98-4fcc-a2e9-28213b9bed82", - "metadata": {}, - "outputs": [], - "source": [ - "base = 'biolip/data/ligand/'\n", - "df['ligand_fn'] = base + df['pdb']+'_'+df['chain']+'_'+df['l_id'].astype(str)+'_'+df['l_chain'].astype(str)+'.pdb'" - ] - }, - { - "cell_type": "code", - "execution_count": 50, - "id": "bd8671da-66ad-40ad-b221-e33228be65f4", - "metadata": {}, - "outputs": [], - "source": [ - "df_complex = pd.read_parquet('data/biolip_complex.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 51, - "id": "08b04d75-c01e-4b26-ae2d-622efae3bd1f", - "metadata": {}, - "outputs": [], - "source": [ - "df_affinity = df_complex[~df_complex['affinity_lit'].isnull() | ~df_complex['affinity_moad'].isnull() \n", - " | ~df_complex['affinity_pdbbind-cn'].isnull() | ~df_complex['affinity_bindingdb'].isnull()].copy()" - ] - }, - { - "cell_type": "code", - "execution_count": 57, - "id": "97af5533-10fe-4419-a998-ed80b7d26690", - "metadata": {}, - "outputs": [], - "source": [ - "from pint import UnitRegistry\n", - "import numpy as np\n", - "import re\n", - "ureg = UnitRegistry()\n", - "\n", - "quantities = ['ki','kd','ka','k1/2','kb','ic50','ec50','km']\n", - "\n", - "others = set()\n", - "def to_uM(affinities):\n", - " lit, moad, pdbbind, bindingdb = affinities\n", - "\n", - " vals = []\n", - " try:\n", - " q = re.split('[=~<>]',str(lit))[0].lower()\n", - " if q not in quantities:\n", - " others.add(q)\n", - " raise\n", - " val = re.split('[=~<>]',str(lit))[1].split(' ')[0]\n", - " val = ureg(val).m_as(ureg.uM)\n", - " vals.append(val)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " q = re.split('[=~<>]',str(lit))[0].lower()\n", - " if q not in quantities:\n", - " others.add(q)\n", - " raise\n", - " val = re.split('[=~<>]',str(lit))[1].split(' ')[0]\n", - " val = ureg(val).m_as(1/ureg.uM)\n", - " vals.append(1/val)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " q = re.split('[=~<>]',str(moad))[0].lower()\n", - " if q not in quantities:\n", - " others.add(q)\n", - " raise\n", - " val = re.split('[=~<>]',str(moad))[1].split(' ')[0]\n", - " val = ureg(val).m_as(ureg.uM)\n", - " vals.append(val)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " q = re.split('[=~<>]',str(moad))[0].lower()\n", - " if q not in quantities:\n", - " others.add(q)\n", - " raise\n", - " val = re.split('[=~<>]',str(moad))[1].split(' ')[0]\n", - " val = ureg(val).m_as(1/ureg.uM)\n", - " vals.append(1/moad)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " q = re.split('[=~<>]',str(pdbbind))[0].lower()\n", - " if q not in quantities:\n", - " others.add(q)\n", - " raise\n", - " val = re.split('[=~<>]',str(pdbbind))[1].split(' ')[0]\n", - " val = ureg(val).m_as(ureg.uM)\n", - " vals.append(val)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " q = re.split('[=~<>]',str(pdbbind))[0].lower()\n", - " if q not in quantities:\n", - " others.add(q)\n", - " raise\n", - " val = re.split('[=~<>]',str(pdbbind))[1].split(' ')[0]\n", - " val = ureg(val).m_as(1/ureg.uM)\n", - " vals.append(1/val)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " q = re.split('[=~<>]',str(bindingdb))[0].lower()\n", - " if q not in quantities:\n", - " others.add(q)\n", - " raise\n", - " val = re.split('[=~<>]',str(bindingdb))[1].split(' ')[0]\n", - " val = ureg(val).m_as(ureg.uM)\n", - " vals.append(val)\n", - " except:\n", - " pass\n", - "\n", - " try:\n", - " q = re.split('[=~<>]',str(bindingdb))[0].lower()\n", - " if q not in quantities:\n", - " others.add(q)\n", - " raise\n", - " val = re.split('[=~<>]',str(bindingdb))[1].split(' ')[0]\n", - " val = ureg(val).m_as(1/ureg.uM)\n", - " vals.append(1/val)\n", - " except:\n", - " pass\n", - "\n", - " if len(vals) > 0:\n", - " vals = np.array(vals)\n", - " return np.mean(vals[~np.isnan(vals)])\n", - " \n", - " return None" - ] - }, - { - "cell_type": "code", - "execution_count": 58, - "id": "d2fab1e6-ec5b-46f9-a4a2-f3744128c777", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "Index(['pdb', 'chain', 'l_id', 'l_chain', 'affinity_lit', 'affinity_moad',\n", - " 'affinity_pdbbind-cn', 'affinity_bindingdb', 'seq', 'ligand_fn',\n", - " 'smiles', 'affinity_uM'],\n", - " dtype='object')" - ] - }, - "execution_count": 58, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_affinity.columns" - ] - }, - { - "cell_type": "code", - "execution_count": 59, - "id": "e21154a9-d3a0-4aa3-986f-cfeebc280da6", - "metadata": {}, - "outputs": [], - "source": [ - "df_affinity['affinity_uM'] = df_affinity[['affinity_lit','affinity_moad','affinity_pdbbind-cn','affinity_bindingdb']].apply(to_uM,axis=1)" - ] - }, - { - "cell_type": "code", - "execution_count": 60, - "id": "6b9526ec-b134-4ecb-8fea-b493c3fdac22", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "{'deltag', 'deltah', 'none'}" - ] - }, - "execution_count": 60, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "others" - ] - }, - { - "cell_type": "code", - "execution_count": 61, - "id": "0fc94de0-823d-4f4f-9904-1c4d1e722c2e", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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pdbchainl_idl_chainaffinity_litaffinity_moadaffinity_pdbbind-cnaffinity_bindingdbseqligand_fnsmilesaffinity_uM
3811gsEAAA1Noneki=1.5uM (GTT EAA)Ki=1.5uM (GTT-EAA)NonePYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKASC...biolip/data/ligand/11gs_EAA_A_1.pdbCC[C@H](C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O)C1.5000
4313gsSASA1Noneki=24uM (SAS)Ki=24uM (SAS)NoneMPPYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKA...biolip/data/ligand/13gs_SAS_A_1.pdbOC(=O)c1cc(/N=N/c2ccc(cc2)S(=O)(=O)Nc2ccccn2)c...24.0000
5316pkBISA1NoneNoneKi=6uM (BIS)NoneEKKSINECDLKGKKVLIRVDFNVPVKNGKITNDYRIRSALPTLKKV...biolip/data/ligand/16pk_BIS_A_1.pdbO[C@@H]1[C@@H](CO[P@](=O)(O[P@@](=O)(C(CCCC(P(...6.0000
5417gsGTXA1NoneNoneNoneKd=10000nMMPPYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKA...biolip/data/ligand/17gs_GTX_A_1.pdbCCCCCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(...10.0000
55181lBNZA1NoneKa=5700M^-1 (BNZ)NoneKd=175000nMMNIFEMLRIDEGLRLKIYKDTEGYYTIGIGHLLTKSPSLNAAKSEL...biolip/data/ligand/181l_BNZ_A_1.pdbc1ccccc1175.0000
.......................................
1051189hvp0E9A1NoneNoneKi=4.5nM (5-mer)NonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM...biolip/data/ligand/9hvp_0E9_A_1.pdbO[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=...0.0045
1051199hvp0E9A1NoneNoneKi=4.5nM (5-mer)NonePQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM...biolip/data/ligand/9hvp_0E9_A_1.pdbO[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=...0.0045
1051249icdNAPA1Nonekd=125uM (NAP)Kd=125uM (NAP)NoneSKVVVPAQGKKITLQNGKLNVPENPIIPYIEGDGIGVDVTPAMLKV...biolip/data/ligand/9icd_NAP_A_1.pdbO[C@@H]1[C@@H](COP(=O)(O)O)O[C@H]([C@@H]1OP(=O...125.0000
1051339lprIIIP1NoneNoneKi=2000nM (4-mer)NoneANIVGGIEYSINNASLCSVGFSVTRGATKGFVTAGHCGTVNATARI...biolip/data/ligand/9lpr_III_P_1.pdbCC(C[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]...2.0000
1051389nseISUB2NoneKi=0.039uM (ISU)NoneNoneKFPRVKNWELGSITYDTLCAQSQQDGPCTPRRCLGSLVLPRKLQTR...biolip/data/ligand/9nse_ISU_B_2.pdbCC[Se]C(=N)N0.0390
\n", - "

12851 rows × 12 columns

\n", - "
" - ], - "text/plain": [ - " pdb chain l_id l_chain affinity_lit affinity_moad \\\n", - "38 11gs EAA A 1 None ki=1.5uM (GTT EAA) \n", - "43 13gs SAS A 1 None ki=24uM (SAS) \n", - "53 16pk BIS A 1 None None \n", - "54 17gs GTX A 1 None None \n", - "55 181l BNZ A 1 None Ka=5700M^-1 (BNZ) \n", - "... ... ... ... ... ... ... \n", - "105118 9hvp 0E9 A 1 None None \n", - "105119 9hvp 0E9 A 1 None None \n", - "105124 9icd NAP A 1 None kd=125uM (NAP) \n", - "105133 9lpr III P 1 None None \n", - "105138 9nse ISU B 2 None Ki=0.039uM (ISU) \n", - "\n", - " affinity_pdbbind-cn affinity_bindingdb \\\n", - "38 Ki=1.5uM (GTT-EAA) None \n", - "43 Ki=24uM (SAS) None \n", - "53 Ki=6uM (BIS) None \n", - "54 None Kd=10000nM \n", - "55 None Kd=175000nM \n", - "... ... ... \n", - "105118 Ki=4.5nM (5-mer) None \n", - "105119 Ki=4.5nM (5-mer) None \n", - "105124 Kd=125uM (NAP) None \n", - "105133 Ki=2000nM (4-mer) None \n", - "105138 None None \n", - "\n", - " seq \\\n", - "38 PYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKASC... \n", - "43 MPPYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKA... \n", - "53 EKKSINECDLKGKKVLIRVDFNVPVKNGKITNDYRIRSALPTLKKV... \n", - "54 MPPYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKA... \n", - "55 MNIFEMLRIDEGLRLKIYKDTEGYYTIGIGHLLTKSPSLNAAKSEL... \n", - "... ... \n", - "105118 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM... \n", - "105119 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM... \n", - "105124 SKVVVPAQGKKITLQNGKLNVPENPIIPYIEGDGIGVDVTPAMLKV... \n", - "105133 ANIVGGIEYSINNASLCSVGFSVTRGATKGFVTAGHCGTVNATARI... \n", - "105138 KFPRVKNWELGSITYDTLCAQSQQDGPCTPRRCLGSLVLPRKLQTR... \n", - "\n", - " ligand_fn \\\n", - "38 biolip/data/ligand/11gs_EAA_A_1.pdb \n", - "43 biolip/data/ligand/13gs_SAS_A_1.pdb \n", - "53 biolip/data/ligand/16pk_BIS_A_1.pdb \n", - "54 biolip/data/ligand/17gs_GTX_A_1.pdb \n", - "55 biolip/data/ligand/181l_BNZ_A_1.pdb \n", - "... ... \n", - "105118 biolip/data/ligand/9hvp_0E9_A_1.pdb \n", - "105119 biolip/data/ligand/9hvp_0E9_A_1.pdb \n", - "105124 biolip/data/ligand/9icd_NAP_A_1.pdb \n", - "105133 biolip/data/ligand/9lpr_III_P_1.pdb \n", - "105138 biolip/data/ligand/9nse_ISU_B_2.pdb \n", - "\n", - " smiles affinity_uM \n", - "38 CC[C@H](C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O)C 1.5000 \n", - "43 OC(=O)c1cc(/N=N/c2ccc(cc2)S(=O)(=O)Nc2ccccn2)c... 24.0000 \n", - "53 O[C@@H]1[C@@H](CO[P@](=O)(O[P@@](=O)(C(CCCC(P(... 6.0000 \n", - "54 CCCCCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(... 10.0000 \n", - "55 c1ccccc1 175.0000 \n", - "... ... ... \n", - "105118 O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=... 0.0045 \n", - "105119 O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=... 0.0045 \n", - "105124 O[C@@H]1[C@@H](COP(=O)(O)O)O[C@H]([C@@H]1OP(=O... 125.0000 \n", - "105133 CC(C[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]... 2.0000 \n", - "105138 CC[Se]C(=N)N 0.0390 \n", - "\n", - "[12851 rows x 12 columns]" - ] - }, - "execution_count": 61, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_affinity[~df_affinity['affinity_uM'].isnull()]" - ] - }, - { - "cell_type": "code", - "execution_count": 63, - "id": "2b483565-3c99-4c42-b2a9-f7b97cd8e80e", - "metadata": {}, - "outputs": [], - "source": [ - "df_affinity.to_parquet('data/biolip.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 64, - "id": "68dd5e45-b31d-492d-a47e-39072b67fa72", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "13645" - ] - }, - "execution_count": 64, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_affinity)" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "cf11317d-bbab-40f1-a8a2-b6fd6126e998", - "metadata": {}, - "outputs": [], - "source": [] - } - ], - "metadata": { - "kernelspec": { - "display_name": "Python 3", - "language": "python", - "name": "python3" - }, - "language_info": { - "codemirror_mode": { - "name": "ipython", - "version": 3 - }, - "file_extension": ".py", - "mimetype": "text/x-python", - "name": "python", - "nbconvert_exporter": "python", - "pygments_lexer": "ipython3", - "version": "3.9.4" - } - }, - "nbformat": 4, - "nbformat_minor": 5 -} diff --git a/biolip.py b/biolip.py deleted file mode 100644 index 4ca2227c30b172854099f059e0eec496dd0b5493..0000000000000000000000000000000000000000 --- a/biolip.py +++ /dev/null @@ -1,41 +0,0 @@ -from mpi4py import MPI -from mpi4py.futures import MPICommExecutor - -from openbabel import pybel -from Bio.PDB import * -parser = PDBParser() - -import os -molecular_weight_cutoff = 2500 -def parse_ligand(fn): - print(fn) - try: - struct = parser.get_structure('lig',fn) - if len(list(struct.get_atoms())) > molecular_weight_cutoff: - raise ValueError - mol = next(pybel.readfile('pdb',fn)) - if mol.molwt > molecular_weight_cutoff: - raise ValueError - smi = mol.write('can').split('\t')[0] - return smi - except: - return None - - -if __name__ == '__main__': - import glob - - comm = MPI.COMM_WORLD - with MPICommExecutor(comm, root=0) as executor: - if executor is not None: - import pandas as pd - - df = pd.read_table('biolip/data/BioLiP_2013-03-6_nr.txt',sep='\t',header=None,usecols=[0,4,5,6,13,14,15,16,19]) - df = df.rename(columns={0:'pdb',4:'chain',5:'l_id',6:'l_chain', - 13: 'affinity_lit',14: 'affinity_moad',15: 'affinity_pdbbind-cn',16:'affinity_bindingdb', - 19: 'seq'}) - base = 'biolip/data/ligand/' - df['ligand_fn'] = base + df['pdb']+'_'+df['chain']+'_'+df['l_id'].astype(str)+'_'+df['l_chain'].astype(str)+'.pdb' - smiles = list(executor.map(parse_ligand, df['ligand_fn'])) - df['smiles'] = smiles - df.to_parquet('data/biolip_complex.parquet') diff --git a/biolip.slurm b/biolip.slurm deleted file mode 100644 index 6a21baea3ef131666be55d8581cc8def9af47f28..0000000000000000000000000000000000000000 --- a/biolip.slurm +++ /dev/null @@ -1,10 +0,0 @@ -#!/bin/bash -#SBATCH -J preprocess_biolip -#SBATCH -p batch -#SBATCH -A BIP214 -#SBATCH -t 3:00:00 -#SBATCH -N 11 -#SBATCH --ntasks-per-node=32 - -export PYTHONUNBUFFERED=1 -srun python biolip.py diff --git a/combine_dbs.ipynb b/combine_dbs.ipynb deleted file mode 100644 index 1eb30b734279950b0f4421c19b90c820b178a855..0000000000000000000000000000000000000000 --- a/combine_dbs.ipynb +++ /dev/null @@ -1,1763 +0,0 @@ -{ - "cells": [ - { - "cell_type": "code", - "execution_count": 2, - "id": "95bd761a-fe51-4a8e-bc70-1365260ba5f8", - "metadata": {}, - "outputs": [], - "source": [ - "import pandas as pd" - ] - }, - { - "cell_type": "code", - "execution_count": 2, - "id": "b0859483-5e19-4280-9f53-0d00a6f22d34", - "metadata": {}, - "outputs": [], - "source": [ - "df_pdbbind = pd.read_parquet('data/pdbbind.parquet')\n", - "df_pdbbind = df_pdbbind[['seq','smiles','affinity_uM']]" - ] - }, - { - "cell_type": "code", - "execution_count": 3, - "id": "f30732b7-7444-47ad-84e7-566e7a6f2f8e", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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seqsmilesaffinity_uM
0MTVPDRSEIAGKWYVVALASNTEFFLREKDKMKMAMARISFLGEDE...CCCCCCCCCCCCCCCCCCCC(=O)O0.026
1APQTITELCSEYRNTQIYTINDKILSYTESMAGKREMVIITFKSGE...OC[C@H]1O[C@H](Oc2cccc(c2)N(=O)=O)[C@@H]([C@H]...500.000
2VETFAFQAEIAQLMSLIINTFYSNKEIFLRELISNSSDALDKIRYE...COc1ccc(cc1)c1c(onc1c1cc(C(C)C)c(cc1O)O)NC(=O)...0.023
3AAPFDKSKNVAQSIDQLIGQTPALYLNKLNNTKAKVVLKMECENPM...OC[C@@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)NC(=O)...6.430
4YITFRSFTAVLIAFFLTLVLSPSFINRLRKIQRKKYTPTMGGIVIL...CO[C@@H]1[C@H](O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1...0.185
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" - ], - "text/plain": [ - " seq \\\n", - "0 MTVPDRSEIAGKWYVVALASNTEFFLREKDKMKMAMARISFLGEDE... \n", - "1 APQTITELCSEYRNTQIYTINDKILSYTESMAGKREMVIITFKSGE... \n", - "2 VETFAFQAEIAQLMSLIINTFYSNKEIFLRELISNSSDALDKIRYE... \n", - "3 AAPFDKSKNVAQSIDQLIGQTPALYLNKLNNTKAKVVLKMECENPM... \n", - "4 YITFRSFTAVLIAFFLTLVLSPSFINRLRKIQRKKYTPTMGGIVIL... \n", - "\n", - " smiles affinity_uM \n", - "0 CCCCCCCCCCCCCCCCCCCC(=O)O 0.026 \n", - "1 OC[C@H]1O[C@H](Oc2cccc(c2)N(=O)=O)[C@@H]([C@H]... 500.000 \n", - "2 COc1ccc(cc1)c1c(onc1c1cc(C(C)C)c(cc1O)O)NC(=O)... 0.023 \n", - "3 OC[C@@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)NC(=O)... 6.430 \n", - "4 CO[C@@H]1[C@H](O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1... 0.185 " - ] - }, - "execution_count": 3, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_pdbbind.head()" - ] - }, - { - "cell_type": "code", - "execution_count": 4, - "id": "2787b9fd-3d6f-4ae3-a3ad-d3539b72782b", - "metadata": {}, - "outputs": [], - "source": [ - "from rdkit import Chem\n", - "from rdkit.Chem import MACCSkeys\n", - "import numpy as np\n", - "\n", - "def get_maccs(smi):\n", - " try:\n", - " mol = Chem.MolFromSmiles(smi)\n", - " arr = np.packbits([0 if c=='0' else 1 for c in MACCSkeys.GenMACCSKeys(mol).ToBitString()])\n", - " return np.pad(arr,(0,3)).view(np.uint32)\n", - " except Exception:\n", - " pass" - ] - }, - { - "cell_type": "code", - "execution_count": 5, - "id": "d1abe1c8-ac66-4289-8964-367a5b18528d", - "metadata": {}, - "outputs": [], - "source": [ - "df_bindingdb = pd.read_parquet('data/bindingdb.parquet')\n", - "df_bindingdb = df_bindingdb[['seq','Ligand SMILES','affinity_uM']].rename(columns={'Ligand SMILES': 'smiles'})" - ] - }, - { - "cell_type": "code", - "execution_count": 6, - "id": "988bab9c-5147-44e2-92ef-902eaf3c5a90", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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seqsmilesaffinity_uM
0PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC10.00024
1PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn...0.00025
2PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=...0.00041
3PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@...0.00080
4PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM...OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H...0.00099
\n", - "
" - ], - "text/plain": [ - " seq \\\n", - "0 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "1 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "2 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "3 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "4 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKM... \n", - "\n", - " smiles affinity_uM \n", - "0 COc1cc2c(Nc3ccc(Br)cc3F)ncnc2cc1OCC1CCN(C)CC1 0.00024 \n", - "1 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(C\\C=C\\c2cn... 0.00025 \n", - "2 O[C@@H]1[C@@H](O)[C@@H](Cc2ccccc2)N(CC2CC2)C(=... 0.00041 \n", - "3 OCCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@... 0.00080 \n", - "4 OCCCCCN1[C@H](Cc2ccccc2)[C@H](O)[C@@H](O)[C@@H... 0.00099 " - ] - }, - "execution_count": 6, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_bindingdb.head()" - ] - }, - { - "cell_type": "code", - "execution_count": 7, - "id": "d7bfee2a-c4e6-48c9-b0c6-52f6a69c7453", - "metadata": {}, - "outputs": [], - "source": [ - "df_moad = pd.read_parquet('data/moad.parquet')\n", - "df_moad = df_moad[['seq','smiles','affinity_uM']]" - ] - }, - { - "cell_type": "code", - "execution_count": 8, - "id": "25553199-1715-40fb-9260-427bdd6c3706", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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seqsmilesaffinity_uM
0NYIVPGEYRVAEGEIEINAGREKTTIRVSNTGDRPIQVGSHIHFVE...NP(=O)(N)O0.000620
1NYIVPGEYRVAEGEIEINAGREKTTIRVSNTGDRPIQVGSHIHFVE...CC(=O)NO2.600000
2MEGMRRPTPTVYVGRVPIGGAHPIAVQSMTNTPTRDVEATTAQVLE...C#CCCOP(=O)(O)OP(=O)(O)O0.580000
3MEGMRRPTPTVYVGRVPIGGAHPIAVQSMTNTPTRDVEATTAQVLE...C#CCOP(=O)(O)OP(=O)(O)O0.770000
4MTDMSIKFELIDVPIPQGTNVIIGQAHFIKTVEDLYEALVTSVPGV...c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3...15.000000
............
25420MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...None127.226463
25421MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...None127.226463
25422MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...None169.204738
25423MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...None169.204738
25424MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...None169.204738
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25425 rows × 3 columns

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" - ], - "text/plain": [ - " seq \\\n", - "0 NYIVPGEYRVAEGEIEINAGREKTTIRVSNTGDRPIQVGSHIHFVE... \n", - "1 NYIVPGEYRVAEGEIEINAGREKTTIRVSNTGDRPIQVGSHIHFVE... \n", - "2 MEGMRRPTPTVYVGRVPIGGAHPIAVQSMTNTPTRDVEATTAQVLE... \n", - "3 MEGMRRPTPTVYVGRVPIGGAHPIAVQSMTNTPTRDVEATTAQVLE... \n", - "4 MTDMSIKFELIDVPIPQGTNVIIGQAHFIKTVEDLYEALVTSVPGV... \n", - "... ... \n", - "25420 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "25421 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "25422 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "25423 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "25424 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "\n", - " smiles affinity_uM \n", - "0 NP(=O)(N)O 0.000620 \n", - "1 CC(=O)NO 2.600000 \n", - "2 C#CCCOP(=O)(O)OP(=O)(O)O 0.580000 \n", - "3 C#CCOP(=O)(O)OP(=O)(O)O 0.770000 \n", - "4 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3... 15.000000 \n", - "... ... ... \n", - "25420 None 127.226463 \n", - "25421 None 127.226463 \n", - "25422 None 169.204738 \n", - "25423 None 169.204738 \n", - "25424 None 169.204738 \n", - "\n", - "[25425 rows x 3 columns]" - ] - }, - "execution_count": 8, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_moad" - ] - }, - { - "cell_type": "code", - "execution_count": 9, - "id": "b2c936bc-cdc8-4bc1-b92d-f8755fd65f0a", - "metadata": {}, - "outputs": [], - "source": [ - "df_biolip = pd.read_parquet('data/biolip.parquet')\n", - "df_biolip = df_biolip[['seq','smiles','affinity_uM']]" - ] - }, - { - "cell_type": "code", - "execution_count": 10, - "id": "cee93018-601d-458b-af44-bd978da7a2bc", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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seqsmilesaffinity_uM
38PYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKASC...CC[C@H](C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O)C1.5000
43MPPYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKA...OC(=O)c1cc(/N=N/c2ccc(cc2)S(=O)(=O)Nc2ccccn2)c...24.0000
53EKKSINECDLKGKKVLIRVDFNVPVKNGKITNDYRIRSALPTLKKV...O[C@@H]1[C@@H](CO[P@](=O)(O[P@@](=O)(C(CCCC(P(...6.0000
54MPPYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKA...CCCCCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(...10.0000
55MNIFEMLRIDEGLRLKIYKDTEGYYTIGIGHLLTKSPSLNAAKSEL...c1ccccc1175.0000
............
105118PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM...O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=...0.0045
105119PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM...O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=...0.0045
105124SKVVVPAQGKKITLQNGKLNVPENPIIPYIEGDGIGVDVTPAMLKV...O[C@@H]1[C@@H](COP(=O)(O)O)O[C@H]([C@@H]1OP(=O...125.0000
105133ANIVGGIEYSINNASLCSVGFSVTRGATKGFVTAGHCGTVNATARI...CC(C[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]...2.0000
105138KFPRVKNWELGSITYDTLCAQSQQDGPCTPRRCLGSLVLPRKLQTR...CC[Se]C(=N)N0.0390
\n", - "

13645 rows × 3 columns

\n", - "
" - ], - "text/plain": [ - " seq \\\n", - "38 PYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKASC... \n", - "43 MPPYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKA... \n", - "53 EKKSINECDLKGKKVLIRVDFNVPVKNGKITNDYRIRSALPTLKKV... \n", - "54 MPPYTVVYFPVRGRCAALRMLLADQGQSWKEEVVTVETWQEGSLKA... \n", - "55 MNIFEMLRIDEGLRLKIYKDTEGYYTIGIGHLLTKSPSLNAAKSEL... \n", - "... ... \n", - "105118 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM... \n", - "105119 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM... \n", - "105124 SKVVVPAQGKKITLQNGKLNVPENPIIPYIEGDGIGVDVTPAMLKV... \n", - "105133 ANIVGGIEYSINNASLCSVGFSVTRGATKGFVTAGHCGTVNATARI... \n", - "105138 KFPRVKNWELGSITYDTLCAQSQQDGPCTPRRCLGSLVLPRKLQTR... \n", - "\n", - " smiles affinity_uM \n", - "38 CC[C@H](C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O)C 1.5000 \n", - "43 OC(=O)c1cc(/N=N/c2ccc(cc2)S(=O)(=O)Nc2ccccn2)c... 24.0000 \n", - "53 O[C@@H]1[C@@H](CO[P@](=O)(O[P@@](=O)(C(CCCC(P(... 6.0000 \n", - "54 CCCCCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(... 10.0000 \n", - "55 c1ccccc1 175.0000 \n", - "... ... ... \n", - "105118 O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=... 0.0045 \n", - "105119 O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=... 0.0045 \n", - "105124 O[C@@H]1[C@@H](COP(=O)(O)O)O[C@H]([C@@H]1OP(=O... 125.0000 \n", - "105133 CC(C[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]... 2.0000 \n", - "105138 CC[Se]C(=N)N 0.0390 \n", - "\n", - "[13645 rows x 3 columns]" - ] - }, - "execution_count": 10, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_biolip" - ] - }, - { - "cell_type": "code", - "execution_count": 11, - "id": "195f92db-fe06-4d03-8500-8d6c310a3347", - "metadata": {}, - "outputs": [], - "source": [ - "df_all = pd.concat([df_pdbbind,df_bindingdb,df_moad,df_biolip]).reset_index()" - ] - }, - { - "cell_type": "code", - "execution_count": 12, - "id": "d25c1e24-6566-4944-a0b4-944b3c8dbc6f", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2283641" - ] - }, - "execution_count": 12, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_all)" - ] - }, - { - "cell_type": "code", - "execution_count": 13, - "id": "c8287da2-cfdf-4d89-b175-f4c6b38ff8ac", - "metadata": {}, - "outputs": [ - { - "name": "stdout", - "output_type": "stream", - "text": [ - "INFO: Pandarallel will run on 32 workers.\n", - "INFO: Pandarallel will use Memory file system to transfer data between the main process and workers.\n" - ] - } - ], - "source": [ - "from pandarallel import pandarallel\n", - "pandarallel.initialize()" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "de5ffc4a-afb7-4a26-8d57-509c2278d750", - "metadata": {}, - "outputs": [], - "source": [ - "df_all['maccs'] = df_all['smiles'].parallel_apply(get_maccs)" - ] - }, - { - "cell_type": "code", - "execution_count": 16, - "id": "59a6706d-dab9-4ee0-8ef6-33537a3622a4", - "metadata": {}, - "outputs": [], - "source": [ - "df_all.to_parquet('data/all_maccs.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 17, - "id": "4ccf2ee5-d369-4c0e-bb91-792765d661bf", - "metadata": {}, - "outputs": [], - "source": [ - "import numpy as np" - ] - }, - { - "cell_type": "code", - "execution_count": 18, - "id": "399f4ace-6dc3-441f-972a-f7b3a103e239", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2283641" - ] - }, - "execution_count": 18, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_all)" - ] - }, - { - "cell_type": "code", - "execution_count": 19, - "id": "8a4bbb18-e62f-4774-ac6b-8a1be68204c1", - "metadata": {}, - "outputs": [], - "source": [ - "df_all = pd.read_parquet('data/all_maccs.parquet')\n", - "df_all = df_all.dropna().reset_index(drop=True)" - ] - }, - { - "cell_type": "code", - "execution_count": 25, - "id": "d210fe56-a7eb-4adc-a77a-14c0c6d0034e", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2277323" - ] - }, - "execution_count": 25, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_all)" - ] - }, - { - "cell_type": "code", - "execution_count": 26, - "id": "d12b365d-98bd-4b61-b836-1a08d2e55418", - "metadata": {}, - "outputs": [], - "source": [ - "maccs = df_all['maccs'].to_numpy()\n", - "#df_reindex[df_reindex.duplicated(keep='first')].reset_index()" - ] - }, - { - "cell_type": "code", - "execution_count": 27, - "id": "80c15210-1af3-436e-970b-f81fc596fb41", - "metadata": {}, - "outputs": [], - "source": [ - "df_maccs = pd.DataFrame(np.vstack(maccs))" - ] - }, - { - "cell_type": "code", - "execution_count": 28, - "id": "30c314b8-8fe7-48ae-a2b8-149de1471b0c", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "0 int64\n", - "1 int64\n", - "2 int64\n", - "3 int64\n", - "4 int64\n", - "5 int64\n", - "dtype: object" - ] - }, - "execution_count": 28, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_maccs.dtypes" - ] - }, - { - "cell_type": "code", - "execution_count": 29, - "id": "70a0a820-4d0c-4472-af96-9c301c0ab204", - "metadata": {}, - "outputs": [], - "source": [ - "df_expand = pd.concat([df_all[['seq','smiles','affinity_uM']],df_maccs],axis=1)" - ] - }, - { - "cell_type": "code", - "execution_count": 30, - "id": "13d092fa-5625-40d0-b7ec-e3405ea20279", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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seqsmilesaffinity_uM012345
0MTVPDRSEIAGKWYVVALASNTEFFLREKDKMKMAMARISFLGEDE...CCCCCCCCCCCCCCCCCCCC(=O)O0.026000805306368272271360890245320136
1APQTITELCSEYRNTQIYTINDKILSYTESMAGKREMVIITFKSGE...OC[C@H]1O[C@H](Oc2cccc(c2)N(=O)=O)[C@@H]([C@H]...500.00002147483648324259020819147325479941167063748288829124
2VETFAFQAEIAQLMSLIINTFYSNKEIFLRELISNSSDALDKIRYE...COc1ccc(cc1)c1c(onc1c1cc(C(C)C)c(cc1O)O)NC(=O)...0.02301310721109655552212337696134773408822951175957252
3AAPFDKSKNVAQSIDQLIGQTPALYLNKLNNTKAKVVLKMECENPM...OC[C@@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)NC(=O)...6.430006685696203319168013457018442133187096220
4YITFRSFTAVLIAFFLTLVLSPSFINRLRKIQRKKYTPTMGGIVIL...CO[C@@H]1[C@H](O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1...0.185010485761107427332210951302440814929844026260436252
..............................
2277318PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM...O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=...0.0045655363932169646983683694036484284858000252
2277319PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM...O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=...0.0045655363932169646983683694036484284858000252
2277320SKVVVPAQGKKITLQNGKLNVPENPIIPYIEGDGIGVDVTPAMLKV...O[C@@H]1[C@@H](COP(=O)(O)O)O[C@H]([C@@H]1OP(=O...125.0000671088641115688962177186950840184317183744193341124
2277321ANIVGGIEYSINNASLCSVGFSVTRGATKGFVTAGHCGTVNATARI...CC(C[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]...2.0000209715213721695814886817463079782067783280204
2277322KFPRVKNWELGSITYDTLCAQSQQDGPCTPRRCLGSLVLPRKLQTR...CC[Se]C(=N)N0.039016614453739673621708801510015504192
\n", - "

2277323 rows × 9 columns

\n", - "
" - ], - "text/plain": [ - " seq \\\n", - "0 MTVPDRSEIAGKWYVVALASNTEFFLREKDKMKMAMARISFLGEDE... \n", - "1 APQTITELCSEYRNTQIYTINDKILSYTESMAGKREMVIITFKSGE... \n", - "2 VETFAFQAEIAQLMSLIINTFYSNKEIFLRELISNSSDALDKIRYE... \n", - "3 AAPFDKSKNVAQSIDQLIGQTPALYLNKLNNTKAKVVLKMECENPM... \n", - "4 YITFRSFTAVLIAFFLTLVLSPSFINRLRKIQRKKYTPTMGGIVIL... \n", - "... ... \n", - "2277318 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM... \n", - "2277319 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM... \n", - "2277320 SKVVVPAQGKKITLQNGKLNVPENPIIPYIEGDGIGVDVTPAMLKV... \n", - "2277321 ANIVGGIEYSINNASLCSVGFSVTRGATKGFVTAGHCGTVNATARI... \n", - "2277322 KFPRVKNWELGSITYDTLCAQSQQDGPCTPRRCLGSLVLPRKLQTR... \n", - "\n", - " smiles affinity_uM \\\n", - "0 CCCCCCCCCCCCCCCCCCCC(=O)O 0.0260 \n", - "1 OC[C@H]1O[C@H](Oc2cccc(c2)N(=O)=O)[C@@H]([C@H]... 500.0000 \n", - "2 COc1ccc(cc1)c1c(onc1c1cc(C(C)C)c(cc1O)O)NC(=O)... 0.0230 \n", - "3 OC[C@@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)NC(=O)... 6.4300 \n", - "4 CO[C@@H]1[C@H](O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1... 0.1850 \n", - "... ... ... \n", - "2277318 O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=... 0.0045 \n", - "2277319 O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=... 0.0045 \n", - "2277320 O[C@@H]1[C@@H](COP(=O)(O)O)O[C@H]([C@@H]1OP(=O... 125.0000 \n", - "2277321 CC(C[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]... 2.0000 \n", - "2277322 CC[Se]C(=N)N 0.0390 \n", - "\n", - " 0 1 2 3 4 5 \n", - "0 0 0 805306368 272271360 890245320 136 \n", - "1 2147483648 3242590208 1914732547 994116706 3748288829 124 \n", - "2 131072 1109655552 2123376961 3477340882 2951175957 252 \n", - "3 0 6685696 2033191680 1345701844 2133187096 220 \n", - "4 1048576 1107427332 2109513024 4081492984 4026260436 252 \n", - "... ... ... ... ... ... ... \n", - "2277318 65536 393216 964698368 369403648 4284858000 252 \n", - "2277319 65536 393216 964698368 369403648 4284858000 252 \n", - "2277320 67108864 1115688962 1771869508 4018431718 3744193341 124 \n", - "2277321 2097152 137216 958148868 1746307978 2067783280 204 \n", - "2277322 16 6144 537396736 2170880 1510015504 192 \n", - "\n", - "[2277323 rows x 9 columns]" - ] - }, - "execution_count": 30, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_expand" - ] - }, - { - "cell_type": "code", - "execution_count": 31, - "id": "30f7fff7-3cfe-41c8-97c9-666f3e256222", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "Index(['seq', 'smiles', 'affinity_uM', 0, 1, 2, 3, 4, 5], dtype='object')" - ] - }, - "execution_count": 31, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_expand.columns" - ] - }, - { - "cell_type": "code", - "execution_count": 32, - "id": "16d2b26e-984f-4c71-af19-a3e711ed9ca2", - "metadata": {}, - "outputs": [], - "source": [ - "df_reindex = df_expand.set_index([0,1,2,3,4,5,'seq'])" - ] - }, - { - "cell_type": "code", - "execution_count": 33, - "id": "27fa2150-8152-444b-ba5b-24bea39fc098", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "Index(['smiles', 'affinity_uM'], dtype='object')" - ] - }, - "execution_count": 33, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_reindex.columns" - ] - }, - { - "cell_type": "code", - "execution_count": 34, - "id": "89edacbc-52f3-4a76-90b0-95273f5e53b3", - "metadata": {}, - "outputs": [], - "source": [ - "df_nr = df_reindex[~df_reindex.duplicated(keep='first')].reset_index()\n", - "df_nr = df_nr.drop(columns=[0,1,2,3,4,5])" - ] - }, - { - "cell_type": "code", - "execution_count": 36, - "id": "6a704c5e-68a6-418f-bcad-8688a13ca1d6", - "metadata": {}, - "outputs": [], - "source": [ - "# final sanity checks" - ] - }, - { - "cell_type": "code", - "execution_count": 37, - "id": "0cad3882-975d-4693-aad1-63ec26646bd0", - "metadata": {}, - "outputs": [ - { - "name": "stderr", - "output_type": "stream", - "text": [ - "/ccs/proj/stf006/glaser/conda-envs/dask/lib/python3.9/site-packages/pandas/core/arraylike.py:358: RuntimeWarning: divide by zero encountered in log\n", - " result = getattr(ufunc, method)(*inputs, **kwargs)\n" - ] - } - ], - "source": [ - "df_nr['neg_log10_affinity_M'] = 6-np.log(df_nr['affinity_uM'])/np.log(10)" - ] - }, - { - "cell_type": "code", - "execution_count": 38, - "id": "c200e29a-3f14-41f4-b620-ccce0eb0d5ce", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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seqsmilesaffinity_uMneg_log10_affinity_M
0MTVPDRSEIAGKWYVVALASNTEFFLREKDKMKMAMARISFLGEDE...CCCCCCCCCCCCCCCCCCCC(=O)O0.02607.585027
1APQTITELCSEYRNTQIYTINDKILSYTESMAGKREMVIITFKSGE...OC[C@H]1O[C@H](Oc2cccc(c2)N(=O)=O)[C@@H]([C@H]...500.00003.301030
2VETFAFQAEIAQLMSLIINTFYSNKEIFLRELISNSSDALDKIRYE...COc1ccc(cc1)c1c(onc1c1cc(C(C)C)c(cc1O)O)NC(=O)...0.02307.638272
3AAPFDKSKNVAQSIDQLIGQTPALYLNKLNNTKAKVVLKMECENPM...OC[C@@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)NC(=O)...6.43005.191789
4YITFRSFTAVLIAFFLTLVLSPSFINRLRKIQRKKYTPTMGGIVIL...CO[C@@H]1[C@H](O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1...0.18506.732828
...............
1838495IVEGSDAEIGMSPWQVMLFRKSPQELLCGASLISDRWVLTAAHCLL...O=C[C@@H](NC(=O)[C@H](Cc1ccc(cc1)OS(O)(O)O)NC(...8.00005.096910
1838496IVEGSDAEIGMSPWQVMLFRKSPQELLCGASLISDRWVLTAAHCLL...CC(C[C@@H](C(=O)N1C=CC[C@H]1C(=O)N)NC(=O)[C@@H...8.00005.096910
1838497PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM...O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=...0.00458.346787
1838498ANIVGGIEYSINNASLCSVGFSVTRGATKGFVTAGHCGTVNATARI...CC(C[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]...2.00005.698970
1838499KFPRVKNWELGSITYDTLCAQSQQDGPCTPRRCLGSLVLPRKLQTR...CC[Se]C(=N)N0.03907.408935
\n", - "

1838500 rows × 4 columns

\n", - "
" - ], - "text/plain": [ - " seq \\\n", - "0 MTVPDRSEIAGKWYVVALASNTEFFLREKDKMKMAMARISFLGEDE... \n", - "1 APQTITELCSEYRNTQIYTINDKILSYTESMAGKREMVIITFKSGE... \n", - "2 VETFAFQAEIAQLMSLIINTFYSNKEIFLRELISNSSDALDKIRYE... \n", - "3 AAPFDKSKNVAQSIDQLIGQTPALYLNKLNNTKAKVVLKMECENPM... \n", - "4 YITFRSFTAVLIAFFLTLVLSPSFINRLRKIQRKKYTPTMGGIVIL... \n", - "... ... \n", - "1838495 IVEGSDAEIGMSPWQVMLFRKSPQELLCGASLISDRWVLTAAHCLL... \n", - "1838496 IVEGSDAEIGMSPWQVMLFRKSPQELLCGASLISDRWVLTAAHCLL... \n", - "1838497 PQITLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMNLPGRWKPKM... \n", - "1838498 ANIVGGIEYSINNASLCSVGFSVTRGATKGFVTAGHCGTVNATARI... \n", - "1838499 KFPRVKNWELGSITYDTLCAQSQQDGPCTPRRCLGSLVLPRKLQTR... \n", - "\n", - " smiles affinity_uM \\\n", - "0 CCCCCCCCCCCCCCCCCCCC(=O)O 0.0260 \n", - "1 OC[C@H]1O[C@H](Oc2cccc(c2)N(=O)=O)[C@@H]([C@H]... 500.0000 \n", - "2 COc1ccc(cc1)c1c(onc1c1cc(C(C)C)c(cc1O)O)NC(=O)... 0.0230 \n", - "3 OC[C@@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)NC(=O)... 6.4300 \n", - "4 CO[C@@H]1[C@H](O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1... 0.1850 \n", - "... ... ... \n", - "1838495 O=C[C@@H](NC(=O)[C@H](Cc1ccc(cc1)OS(O)(O)O)NC(... 8.0000 \n", - "1838496 CC(C[C@@H](C(=O)N1C=CC[C@H]1C(=O)N)NC(=O)[C@@H... 8.0000 \n", - "1838497 O[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)C)NC(=... 0.0045 \n", - "1838498 CC(C[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]... 2.0000 \n", - "1838499 CC[Se]C(=N)N 0.0390 \n", - "\n", - " neg_log10_affinity_M \n", - "0 7.585027 \n", - "1 3.301030 \n", - "2 7.638272 \n", - "3 5.191789 \n", - "4 6.732828 \n", - "... ... \n", - "1838495 5.096910 \n", - "1838496 5.096910 \n", - "1838497 8.346787 \n", - "1838498 5.698970 \n", - "1838499 7.408935 \n", - "\n", - "[1838500 rows x 4 columns]" - ] - }, - "execution_count": 38, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_nr" - ] - }, - { - "cell_type": "code", - "execution_count": 52, - "id": "7f4027a2-0a5f-47bf-8a34-0c6a73b9b112", - "metadata": {}, - "outputs": [], - "source": [ - "df = df_nr[np.isfinite(df_nr['neg_log10_affinity_M'])].copy()" - ] - }, - { - "cell_type": "code", - "execution_count": 53, - "id": "eb99774f-9bcc-454d-b5e5-a8470223d6ca", - "metadata": {}, - "outputs": [], - "source": [ - "from rdkit import Chem\n", - "def make_canonical(smi):\n", - " try:\n", - " return Chem.MolToSmiles(Chem.MolFromSmiles(smi))\n", - " except:\n", - " return smi" - ] - }, - { - "cell_type": "code", - "execution_count": 54, - "id": "4d44bd8e-f2e1-44b4-aea7-40b4437baf44", - "metadata": {}, - "outputs": [], - "source": [ - "df['smiles_can'] = df['smiles'].parallel_apply(make_canonical)" - ] - }, - { - "cell_type": "code", - "execution_count": 55, - "id": "07ffdeb1-f4fa-4776-9fea-a18439e03d2e", - "metadata": {}, - "outputs": [], - "source": [ - "df = df[(df['neg_log10_affinity_M']>0) & (df['neg_log10_affinity_M']<15)].reset_index()" - ] - }, - { - "cell_type": "code", - "execution_count": 56, - "id": "8f949038-d07d-4d3a-a47e-b825cc9018ca", - "metadata": {}, - "outputs": [], - "source": [ - "from sklearn.preprocessing import StandardScaler" - ] - }, - { - "cell_type": "code", - "execution_count": 57, - "id": "0c027988-0b44-4010-ad61-7d70eead1654", - "metadata": {}, - "outputs": [], - "source": [ - "scaler = StandardScaler()" - ] - }, - { - "cell_type": "code", - "execution_count": 58, - "id": "6aeba020-b6ff-4633-902e-4df74463eb2f", - "metadata": {}, - "outputs": [], - "source": [ - "df['affinity'] = scaler.fit_transform(df['neg_log10_affinity_M'].values.reshape(-1,1))" - ] - }, - { - "cell_type": "code", - "execution_count": 59, - "id": "91196eee-5fd0-4aa4-927a-5c1a3f436ac8", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "(array([6.50604534]), array([2.43319576]))" - ] - }, - "execution_count": 59, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "scaler.mean_, scaler.var_" - ] - }, - { - "cell_type": "code", - "execution_count": 60, - "id": "56269dcb-e691-4759-949d-7bfdd02f5fd4", - "metadata": {}, - "outputs": [], - "source": [ - "df = df.drop(columns='index')" - ] - }, - { - "cell_type": "code", - "execution_count": 7, - "id": "c6c64066-4032-4247-a8b9-00388176cc7b", - "metadata": {}, - "outputs": [], - "source": [ - "df = df.astype({'affinity_uM': 'float32', 'neg_log10_affinity_M': 'float32', 'affinity': 'float32'})\n", - "df.to_parquet('data/all.parquet')\n", - "\n", - "#df = pd.read_parquet('data/all.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 14, - "id": "469cf0dd-7b87-4245-973c-2a445e1fcca9", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "Index(['seq', 'smiles', 'affinity_uM', 'neg_log10_affinity_M', 'smiles_can',\n", - " 'affinity'],\n", - " dtype='object')" - ] - }, - "execution_count": 14, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df.columns" - ] - }, - { - "cell_type": "code", - "execution_count": 63, - "id": "d91c0d91-474c-4ab2-9a5e-3b7861f7a832", - "metadata": {}, - "outputs": [ - { - "data": { - "image/png": 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\n", - "text/plain": [ - "
" - ] - }, - "metadata": { - "needs_background": "light" - }, - "output_type": "display_data" - } - ], - "source": [ - "ax = df['neg_log10_affinity_M'].hist(bins=100,density=True)\n", - "ax.set_xlabel('-$\\log_{10}$ affinity[M]',fontsize=16)\n", - "ax.set_ylabel('probability',fontsize=16)\n", - "ax.figure.savefig('affinity_neglog10_M.pdf')" - ] - }, - { - "cell_type": "code", - "execution_count": 64, - "id": "0e895ef5-1812-46c7-a4c2-dd6619b49157", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "1836729" - ] - }, - "execution_count": 64, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df)" - ] - }, - { - "cell_type": "code", - "execution_count": 65, - "id": "3af855d3-a943-4574-985c-540d3f6b6f80", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "{'with_mean': True,\n", - " 'with_std': True,\n", - " 'copy': True,\n", - " 'n_features_in_': 1,\n", - " 'n_samples_seen_': 1836729,\n", - " 'mean_': array([6.50604534]),\n", - " 'var_': array([2.43319576]),\n", - " 'scale_': array([1.55987043])}" - ] - }, - "execution_count": 65, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "scaler.__dict__" - ] - }, - { - "cell_type": "code", - "execution_count": 66, - "id": "15f8d5b9-37d5-453e-a6df-df6510cc5c81", - "metadata": {}, - "outputs": [], - "source": [ - "# output the normalization\n", - "\n", - "import json\n", - "\n", - "class NumpyEncoder(json.JSONEncoder):\n", - " def default(self, obj):\n", - " if isinstance(obj, np.ndarray):\n", - " return obj.tolist()\n", - " if isinstance(obj, np.int64):\n", - " return int(obj)\n", - " return json.JSONEncoder.default(self, obj)\n", - " \n", - "json.dump(scaler.__dict__,open('data/scaling.json','w'),cls=NumpyEncoder)" - ] - }, - { - "cell_type": "markdown", - "id": "210b39d3-505b-4a6e-b186-35e660f4d510", - "metadata": {}, - "source": [ - "**without KRAS**" - ] - }, - { - "cell_type": "code", - "execution_count": 67, - "id": "8dec95dc-a014-4d39-ae51-8de981173573", - "metadata": {}, - "outputs": [], - "source": [ - "smiles_sotorasib = 'C=CC(=O)N1CCN(c2nc(=O)n(-c3c(C)ccnc3C(C)C)c3nc(-c4c(O)cccc4F)c(F)cc23)[C@@H](C)C1'\n", - "seq_kras_wt = 'MTEYKLVVVGAGGVGKSALTIQLIQNHFVDEYDPTIEDSYRKQVVIDGETCLLDILDTAGQEEYSAMRDQYMRTGEGFLCVFAINNTKSFEDIHHYREQIKRVKDSEDVPMVLVGNKCDLPSRTVDTKQAQDLARSYGIPFIETSAKTRQRVEDAFYTLVREIRQYRLKKISKEEKTPGCVKIKKCIIM'" - ] - }, - { - "cell_type": "code", - "execution_count": 68, - "id": "3f90eadd-d7e4-4104-961f-adaf5437e24b", - "metadata": {}, - "outputs": [], - "source": [ - "df_nokras = df[~df.seq.str.startswith(seq_kras_wt[:20])]" - ] - }, - { - "cell_type": "code", - "execution_count": 69, - "id": "f5f5335a-8f28-4058-8647-fcc8f7d2f841", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "1836326" - ] - }, - "execution_count": 69, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_nokras)" - ] - }, - { - "cell_type": "code", - "execution_count": 10, - "id": "47966268-c97c-4bd9-9c90-eb568249f2ef", - "metadata": {}, - "outputs": [], - "source": [ - "#df_nokras = df_nokras.astype({'affinity_uM': 'float32', 'neg_log10_affinity_M': 'float32', 'affinity': 'float32'})\n", - "#df_nokras.to_parquet('data/all_nokras.parquet')\n", - "#df_nokras = pd.read_parquet('data/all_nokras.parquet')" - ] - }, - { - "cell_type": "markdown", - "id": "4838f164-aed7-4f2d-a047-df647dfb8ea6", - "metadata": {}, - "source": [ - "**with covalently binding ligands only**" - ] - }, - { - "cell_type": "code", - "execution_count": 89, - "id": "c0d250a3-5680-446c-9c98-7d6623643304", - "metadata": {}, - "outputs": [], - "source": [ - "from rdkit.Chem import SDMolSupplier\n", - "suppl = SDMolSupplier('data/CovPDB_ligands.sdf')\n" - ] - }, - { - "cell_type": "code", - "execution_count": 90, - "id": "0c7c0b26-1f2a-4b80-8117-f1e02719aac9", - "metadata": {}, - "outputs": [ - { - "name": "stderr", - "output_type": "stream", - "text": [ - "RDKit WARNING: [13:44:45] Warning: molecule is tagged as 3D, but all Z coords are zero\n", - "RDKit WARNING: [13:44:45] Warning: molecule is tagged as 3D, but all Z coords are zero\n", - "RDKit WARNING: [13:44:45] Warning: molecule is tagged as 3D, but all Z coords are zero\n", - "RDKit WARNING: [13:44:45] Warning: molecule is tagged as 3D, but all Z coords are zero\n", - "RDKit WARNING: [13:44:45] Warning: molecule is tagged as 3D, but all Z coords are zero\n", - "RDKit WARNING: [13:44:45] Warning: molecule is tagged as 3D, but all Z coords are zero\n", - "RDKit WARNING: [13:44:45] Warning: molecule is tagged as 3D, but all Z coords are zero\n", - "RDKit WARNING: [13:44:45] Warning: molecule is tagged as 3D, but all Z coords are zero\n" - ] - } - ], - "source": [ - "from rdkit import Chem\n", - "cov_smiles = [Chem.MolToSmiles(m) for m in suppl]" - ] - }, - { - "cell_type": "code", - "execution_count": 74, - "id": "258f593c-1cba-45cb-936e-8c1360075926", - "metadata": {}, - "outputs": [], - "source": [ - "df_cov = df[df['smiles'].isin(cov_smiles)]" - ] - }, - { - "cell_type": "code", - "execution_count": 12, - "id": "ee3fa0bc-9ad3-4ea7-9393-cbc7504f634c", - "metadata": {}, - "outputs": [], - "source": [ - "df_cov = df_cov.astype({'affinity_uM': 'float32', 'neg_log10_affinity_M': 'float32', 'affinity': 'float32'})\n", - "#df_cov.reset_index(drop=True).to_parquet('data/cov.parquet')\n", - "#df_cov = pd.read_parquet('data/cov.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 77, - "id": "5c12fedc-4236-4587-a744-c0c9ec21ceaa", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "346" - ] - }, - "execution_count": 77, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_cov)" - ] - }, - { - "cell_type": "code", - "execution_count": 78, - "id": "1b73cea5-e6d9-427f-a31e-7ab38b5e6e4e", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "2.703125" - ] - }, - "execution_count": 78, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "346/128" - ] - }, - { - "cell_type": "code", - "execution_count": 80, - "id": "2d1d2955-7839-45e0-9a11-07dda2d51b24", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "" - ] - }, - "execution_count": 80, - "metadata": {}, - "output_type": "execute_result" - }, - { - "data": { - "image/png": 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}, - "execution_count": 96, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_cov)" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "b8af53a6-5203-4889-9c4b-31140da5fc5b", - "metadata": {}, - "outputs": [], - "source": [] - } - ], - "metadata": { - "kernelspec": { - "display_name": "Python 3 (ipykernel)", - "language": "python", - "name": "python3" - }, - "language_info": { - "codemirror_mode": { - "name": "ipython", - "version": 3 - }, - "file_extension": ".py", - "mimetype": "text/x-python", - "name": "python", - "nbconvert_exporter": "python", - "pygments_lexer": "ipython3", - "version": "3.9.6" - } - }, - "nbformat": 4, - "nbformat_minor": 5 -} diff --git a/combine_predictions.py b/combine_predictions.py deleted file mode 100644 index bad5d9bfd9f7dbd0c6190e14af9bde1869dd9883..0000000000000000000000000000000000000000 --- a/combine_predictions.py +++ /dev/null @@ -1,10 +0,0 @@ -import dask.dataframe as dd -import sys - -if __name__ == '__main__': - import glob - - filenames = glob.glob(sys.argv[2]) - - ddf = dd.read_parquet(filenames) - ddf.compute().to_parquet(sys.argv[1]) diff --git a/data/.gitattributes b/data/.gitattributes deleted file mode 100644 index 18385176dad27bc6ee529166260615a488584635..0000000000000000000000000000000000000000 --- a/data/.gitattributes +++ /dev/null @@ -1 +0,0 @@ -all_512.parquet filter=lfs diff=lfs merge=lfs -text diff --git a/data/all.parquet b/data/all.parquet deleted file mode 100644 index fb449808c85b90b4fc3239c32a02c15400720091..0000000000000000000000000000000000000000 --- a/data/all.parquet +++ /dev/null @@ -1,3 +0,0 @@ -version https://git-lfs.github.com/spec/v1 -oid sha256:d50f4cae794298f32c39f75a9e8603528d20e50e4fa757025def412f5b2a78d8 -size 227593647 diff --git a/data/all_512.parquet b/data/all_512.parquet deleted file mode 100644 index c68970b343be4a9086e69e9a7358d89c6791e01b..0000000000000000000000000000000000000000 --- a/data/all_512.parquet +++ /dev/null @@ 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--- a/data/moad_complex.parquet +++ /dev/null @@ -1,3 +0,0 @@ -version https://git-lfs.github.com/spec/v1 -oid sha256:93ede51816dbac2bea4c6c22d4d94b144a929af378515ed9650b1e49cf94733b -size 989849 diff --git a/data/pdbbind.parquet b/data/pdbbind.parquet deleted file mode 100644 index 0a46e16da46e900df1d44f441a012417cabfc70e..0000000000000000000000000000000000000000 --- a/data/pdbbind.parquet +++ /dev/null @@ -1,3 +0,0 @@ -version https://git-lfs.github.com/spec/v1 -oid sha256:3bd6c0780d51dbb3a828a0c45de10d6364f4499b4e964f0de6e3036f6792a7f2 -size 6353090 diff --git a/data/pdbbind_complex.parquet b/data/pdbbind_complex.parquet deleted file mode 100644 index ce3a77eb1c143de3aff0a06ec18e9be145c9ef88..0000000000000000000000000000000000000000 --- a/data/pdbbind_complex.parquet +++ /dev/null @@ -1,3 +0,0 @@ -version https://git-lfs.github.com/spec/v1 -oid sha256:1c63549d34e14cb8a73cd21dee31461728cd7a37a80cf8fc488f0fb5e024c368 -size 6078339 diff --git a/data/scaling.json b/data/scaling.json deleted file mode 100644 index b1e6d139de1db55dbbd523466a70df100ee634bf..0000000000000000000000000000000000000000 --- a/data/scaling.json +++ /dev/null @@ -1 +0,0 @@ -{"with_mean": true, "with_std": true, "copy": true, "n_features_in_": 1, "n_samples_seen_": 1927202, "mean_": [6.51286529169358], "var_": [2.4379994951935378], "scale_": [1.5614094578916633]} \ No newline at end of file diff --git a/dcoid.py b/dcoid.py deleted file mode 100644 index 71853dea4dc7017e480d6381856839c4c79ab7ed..0000000000000000000000000000000000000000 --- a/dcoid.py +++ /dev/null @@ -1,85 +0,0 @@ -from mpi4py import MPI -from mpi4py.futures import MPICommExecutor - -from Bio.PDB import PDBParser, PDBIO, Select, PPBuilder -import warnings - -import tempfile -import os -import sys -from rdkit import Chem - -import pandas as pd - -def is_het(residue): - res = residue.id[0] - return res != " " and res != "W" - - -class ResidueSelect(Select): - def __init__(self, het): - self.het = het - - def accept_residue(self, residue): - """ Recognition of heteroatoms - Remove water molecules """ - return (self.het and is_het(residue) or not self.het and not is_het(residue)) - -def get_complex(fn): - try: - parser = PDBParser() - io = PDBIO() - structure = parser.get_structure('complex',fn) - io.set_structure(structure) - - with tempfile.NamedTemporaryFile(mode='w',delete=False) as f: - name_receptor = f.name - - with tempfile.NamedTemporaryFile(mode='w',delete=False) as f: - name_ligand = f.name - - io.save(name_receptor,ResidueSelect(het=False)) - io.save(name_ligand,ResidueSelect(het=True)) - - parser = PDBParser() - receptor = parser.get_structure('protein',name_receptor) - ppb = PPBuilder() - seq = [] - for pp in ppb.build_peptides(structure): - seq.append(str(pp.get_sequence())) - seq = ''.join(seq) - - mol = Chem.MolFromPDBFile(name_ligand) - smiles = Chem.MolToSmiles(mol) - - os.unlink(name_ligand) - os.unlink(name_receptor) - - return seq, smiles - - except Exception as e: - print(e) - pass - - -if __name__ == '__main__': - import glob - - filenames = glob.glob(sys.argv[2]) - comm = MPI.COMM_WORLD - with MPICommExecutor(comm, root=0) as executor: - if executor is not None: - result = executor.map(get_complex, filenames) - - names = [] - all_seq = [] - all_smiles = [] - for n,r in zip(filenames,result): - try: - all_seq.append(r[0]) - all_smiles.append(r[1]) - names.append(os.path.basename(n)) - except: - pass - df = pd.DataFrame({'name': names, 'seq': all_seq, 'smiles': all_smiles}) - df.to_parquet(sys.argv[1]) - diff --git a/dcoid.slurm b/dcoid.slurm deleted file mode 100644 index b069238667a375966f84ad646805959228865d26..0000000000000000000000000000000000000000 --- a/dcoid.slurm +++ /dev/null @@ -1,10 +0,0 @@ -#!/bin/bash -#SBATCH -J preprocess_dcoid -#SBATCH -p batch -#SBATCH -A STF006 -#SBATCH -t 3:00:00 -#SBATCH -N 20 -##SBATCH --ntasks-per-node=16 - -srun python dcoid.py data/dcoid_actives.parquet "/gpfs/alpine/world-shared/bip214/binding_affinity/dcoid/actives/*pdb" -srun python dcoid.py data/dcoid_decoys.parquet "/gpfs/alpine/world-shared/bip214/binding_affinity/dcoid/decoys/*pdb" diff --git a/dcoid_combine.py b/dcoid_combine.py deleted file mode 100644 index dd63e2a039cbfefe2cf63b1d0c861e405cad9562..0000000000000000000000000000000000000000 --- a/dcoid_combine.py +++ /dev/null @@ -1,13 +0,0 @@ -import pandas as pd -import sys - -if __name__ == '__main__': - import glob - - df_actives = pd.read_parquet(sys.argv[1]) - df_decoys = pd.read_parquet(sys.argv[2]) - - df_actives['active'] = pd.Series([True]*len(df_actives)) - df_decoys['active'] = pd.Series([False]*len(df_decoys)) - - pd.concat([df_actives,df_decoys]).to_parquet(sys.argv[3]) diff --git a/dcoid_rf2.py b/dcoid_rf2.py deleted file mode 100644 index 7ef329e45445b5fcfb302bfe7f1dee23c5b7c683..0000000000000000000000000000000000000000 --- a/dcoid_rf2.py +++ /dev/null @@ -1,77 +0,0 @@ -from mpi4py import MPI -from mpi4py.futures import MPICommExecutor - - -from oddt.scoring.functions import RFScore -import oddt -from Bio.PDB import PDBParser, PDBIO, Select -import tempfile -import os -import sys - -import pandas as pd - -scorer = RFScore.rfscore.load(version=2) - -def is_het(residue): - res = residue.id[0] - return res != " " and res != "W" - -class ResidueSelect(Select): - def __init__(self, het): - self.het = het - - def accept_residue(self, residue): - """ Recognition of heteroatoms - Remove water molecules """ - return (self.het and is_het(residue) or not self.het and not is_het(residue)) - -def get_complex(fn): - try: - io = PDBIO() - parser = PDBParser() - - structure = parser.get_structure('complex',fn) - io.set_structure(structure) - - with tempfile.NamedTemporaryFile(mode='w',delete=False) as f: - name_receptor = f.name - - with tempfile.NamedTemporaryFile(mode='w',delete=False) as f: - name_ligand = f.name - - io.save(name_receptor,ResidueSelect(het=False)) - io.save(name_ligand,ResidueSelect(het=True)) - - receptor = next(oddt.toolkit.readfile('pdb',name_receptor)) - ligand = next(oddt.toolkit.readfile('pdb',name_ligand)) - - scorer.set_protein(receptor) - scorer.predict_ligand(ligand) - - os.unlink(name_ligand) - os.unlink(name_receptor) - return float(ligand.data['rfscore_v2']) - except Exception as e: - print(e) - pass - -if __name__ == '__main__': - import glob - - filenames = glob.glob(sys.argv[2]) - comm = MPI.COMM_WORLD - with MPICommExecutor(comm, root=0) as executor: - if executor is not None: - result = executor.map(get_complex, filenames) - - names = [] - scores = [] - for n,r in zip(filenames,result): - try: - scores.append(r) - names.append(os.path.basename(n)) - except: - pass - df = pd.DataFrame({'name': names, 'rf2': scores}) - df.to_parquet(sys.argv[1]) - diff --git a/dcoid_rf2.slurm b/dcoid_rf2.slurm deleted file mode 100644 index d3188d5fa9a262bd9205f7d4cd80585a8aba7033..0000000000000000000000000000000000000000 --- a/dcoid_rf2.slurm +++ /dev/null @@ -1,10 +0,0 @@ -#!/bin/bash -#SBATCH -J dcoid_rf2 -#SBATCH -p batch -#SBATCH -A STF006 -#SBATCH -t 1:00:00 -#SBATCH -N 8 -#SBATCH --ntasks-per-node=32 - -srun python dcoid_rf2.py data/dcoid_rf2_actives.parquet "/gpfs/alpine/world-shared/bip214/binding_affinity/dcoid/actives/*pdb" -srun python dcoid_rf2.py data/dcoid_rf2_decoys.parquet "/gpfs/alpine/world-shared/bip214/binding_affinity/dcoid/decoys/*pdb" diff --git a/deepcoy_combine.py b/deepcoy_combine.py deleted file mode 100644 index 28c52dbc6b2408443142410bbfd4eebd4a3ed55e..0000000000000000000000000000000000000000 --- a/deepcoy_combine.py +++ /dev/null @@ -1,56 +0,0 @@ -import dask.dataframe as dd -import pandas as pd -import sys -import os -import numpy as np - -from Bio.PDB import PDBList -from Bio import SeqIO - -from rdkit import Chem - -import warnings - -def get_sequence(pdb_id): - try: - pdbfile = PDBList().retrieve_pdb_file(pdb_id.upper(),file_format='pdb',pdir='/tmp') - seq = str(next(SeqIO.parse(pdbfile, "pdb-seqres")).seq) - os.unlink(pdbfile) - - return seq - except Exception as e: - print(e) - pass - -def make_canonical(smi): - return Chem.MolToSmiles(Chem.MolFromSmiles(smi)) - -if __name__ == '__main__': - import glob - - filenames = glob.glob(sys.argv[3]) - - seqs = [] - smiles = [] - active = [] - - targets = pd.read_csv(sys.argv[1],sep=' ',keep_default_na=False) - for fn in filenames: - df = pd.read_csv(fn,header=None,sep=' ') - df[0] = df[0].apply(make_canonical) - df[1] = df[1].apply(make_canonical) - actives = df[0].unique() - decoys = df[1].unique() - smiles += actives.tolist()+decoys.tolist() - active += [True]*len(actives) + [False]*len(decoys) - split = os.path.basename(fn).split('-') - target = split[2].upper() - if len(split) > 5: - target += '-'+split[3].upper() - print(target) - seq = get_sequence(targets[targets.name.str.upper()==target].pdb.values[0]) - seqs += [seq]*(len(actives)+len(decoys)) - - ddf = dd.from_pandas(pd.DataFrame({'seq': seqs, 'smiles': smiles, 'active': active}),npartitions=1) - ddf = ddf.repartition(partition_size='1M') - ddf.to_parquet(sys.argv[2]) diff --git a/default/binding_affinity-covalent.parquet b/default/binding_affinity-covalent.parquet new file mode 100644 index 0000000000000000000000000000000000000000..beb7c2042246cc93c1310681f4c23e04b515998f Binary files /dev/null and b/default/binding_affinity-covalent.parquet differ diff --git a/default/binding_affinity-no_kras.parquet b/default/binding_affinity-no_kras.parquet new file mode 100644 index 0000000000000000000000000000000000000000..142e3c89321f1a69970e3a392e6f246bbb351423 --- /dev/null +++ b/default/binding_affinity-no_kras.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:58df893952f81cb8e5ac5947c0dc0e37837ac0af68d8597539c5538528a011b0 +size 140636252 diff --git a/default/binding_affinity-train.parquet b/default/binding_affinity-train.parquet new file mode 100644 index 0000000000000000000000000000000000000000..a55a0654c8e3e56afa3725c94160610a8f4d1e88 --- /dev/null +++ b/default/binding_affinity-train.parquet @@ -0,0 +1,3 @@ +version https://git-lfs.github.com/spec/v1 +oid sha256:3db1f2eb0675e26c64284bb69b8ea2d4d122411f882de61205808cfd022435a4 +size 140557906 diff --git a/dekois_targets.txt b/dekois_targets.txt deleted file mode 100644 index a96490cb9fd293f422180cb0f1a7ad390e0ca913..0000000000000000000000000000000000000000 --- a/dekois_targets.txt +++ /dev/null @@ -1,84 +0,0 @@ -name pdb -11betaHSD1 3tfq -17betaHSD1 3klm -A2A 3eml -ACE 1uze -ACE2 1r4l -ACHE 1eve -ADAM17 3ewj -ADRB2 3ny9 -AKT1 3qkl -ALR2 1ah3 -AR 1e3g -AURKA 3fdn -AURKB 2vgo -BCL2 2w3l -BRAF 3skc -CATL 3bc3 -CDK2 1ckp -COX1 3kk6 -COX2 1cx2 -CTSK 3kx1 -CYP2A6 1z11 -DHFR 1s3v -EGFR 1m17 -EPHB4 2vwz -ERBB2 3pp0 -ER-beta 3oll -FGFR1 1agw -FGFR1 1agw -FKBP1A 2dg3 -FXA 1f0r -GBA 2wcg -GR 1nhz -GSK3B 3i4b -HDAC2 3max -HDAC8 3sff -HIV1PR 3nu3 -HIV1RT 1s6p -HMGR 1hw8 -HSP90 1uy6 -IGF1R 3nw7 -INHA 1p44 -ITK 3mj1 -JAK3 3lxl -KNK1 33lj -JNK1 3elj -JNK2 3npc -JNK3 2b1p -KIF11 3k5e -LCK 3mpm -MDM2 3lbk -MK2 3kc3 -MMP2 1hov -NA 1a4g -P38-alpha 1ouk -PARP-1 3l3m -PDE4b 3frg -PDE5 1xp0 -PDK1 2xch -PI3Kg 3dbs -PIM-1 3r04 -PIM-2 2iwi -PNP 1b8o -PPARa 2p54 -PPARg 1fm9 -PR 2w8y -PRKCQ 1xjd -PYGL-in 1xoi -PYGL-out 3dds -QPCT 2afx -ROCK-1 3v8s -RXR 2p1t -SARS-HCoV 2z94 -SIRT2 1j8f -SRC 2src -THROMBIN 3rm2 -TIE2 2oo8 -TK 1w4r -TP 1uou -TPA 1a5h -TS 1i00 -uPA 3mhw -VEGFR1 3hng -VEGFR2 3c7q diff --git a/dude.py b/dude.py deleted file mode 100644 index 53cfe32588abac2de4b99250629d404fa8af08bd..0000000000000000000000000000000000000000 --- a/dude.py +++ /dev/null @@ -1,74 +0,0 @@ -from mpi4py import MPI -from mpi4py.futures import MPICommExecutor - -from Bio.PDB import PDBParser, PPBuilder -import warnings - -import gzip -import tempfile -import os -from rdkit import Chem - -import pandas as pd - -def open_ligands(fn): - with tempfile.NamedTemporaryFile(mode='w+b',delete=False) as f: - with gzip.open(fn,'rb') as g: - f.write(g.read()) - name = f.name - - suppl = Chem.SDMolSupplier(name) - os.unlink(name) - return suppl - -def get_ligands(path): - try: - parser = PDBParser() - with warnings.catch_warnings(): - warnings.simplefilter("ignore") - structure = parser.get_structure('protein',path+'/receptor.pdb') - ppb = PPBuilder() - seq = [] - for pp in ppb.build_peptides(structure): - seq.append(str(pp.get_sequence())) - seq = ''.join(seq) - - name = os.path.basename(path) - - decoys = open_ligands(path+'/decoys_final.sdf.gz') - actives = open_ligands(path+'/actives_final.sdf.gz') - - actives_smiles = [] - for m in actives: - try: - actives_smiles.append(Chem.MolToSmiles(m)) - except: - pass - - decoys_smiles = [] - for m in decoys: - try: - decoys_smiles.append(Chem.MolToSmiles(m)) - except: - pass - - all_smiles = actives_smiles + decoys_smiles - all_active = [True]*len(actives_smiles) + [False]*len(decoys_smiles) - names = [name]*len(all_active) - seqs = [seq]*len(all_active) - df = pd.DataFrame({'name': names, 'seq': seqs, 'smiles': all_smiles, 'active': all_active}) - - df.to_parquet(path+'/ligands.parquet') - except Exception as e: - print(e) - pass - - -if __name__ == '__main__': - import glob - - filenames = glob.glob('DUDE/all/*') - comm = MPI.COMM_WORLD - with MPICommExecutor(comm, root=0) as executor: - if executor is not None: - executor.map(get_ligands, filenames) diff --git a/dude.slurm b/dude.slurm deleted file mode 100644 index 91096450ef103d1bb4d01caa15e4f8d4d039d5a6..0000000000000000000000000000000000000000 --- a/dude.slurm +++ /dev/null @@ -1,9 +0,0 @@ -#!/bin/bash -#SBATCH -J preprocess_dude -#SBATCH -p gpu -#SBATCH -A STF006 -#SBATCH -t 3:00:00 -#SBATCH -N 8 -#SBATCH --ntasks-per-node=16 - -srun python dude.py diff --git a/dude_combine.py b/dude_combine.py deleted file mode 100644 index 0da93599318b291d1578c8b5b94f6fc9f3ea76be..0000000000000000000000000000000000000000 --- a/dude_combine.py +++ /dev/null @@ -1,10 +0,0 @@ -import dask.dataframe as dd - -if __name__ == '__main__': - import glob - - filenames = glob.glob('DUDE/all/*/ligands.parquet') - - ddf = dd.read_parquet(filenames) - ddf = ddf.repartition(partition_size='1M') - ddf.to_parquet('data/dude') diff --git a/dude_targets.txt b/dude_targets.txt deleted file mode 100644 index 7bc1762469dff3243519fcfcfe88244fed64cbe8..0000000000000000000000000000000000000000 --- a/dude_targets.txt +++ /dev/null @@ -1,104 +0,0 @@ -name pdb -AA2AR 3eml -ABL1 2hzi -ACE 3bkl -ACES 1e66 -ADA 2e1w -ADA17 2oi0 -ADRB1 2vt4 -ADRB2 3ny8 -AKT1 3cqw -AKT2 3d0e -ALDR 2hv5 -AMPC 1l2s -ANDR 2am9 -AOFB 1s3b -BACE1 3l5d -BRAF 3d4q -CAH2 1bcd -CASP3 2cnk -CDK2 1h00 -COMT 3bwm -CP2C9 1r9o -CP3A4 3nxu -CSF1R 3krj -CXCR4 3odu -DEF 1lru -DHI1 3frj -DPP4 2i78 -DRD3 3pbl -DYR 3nxo -EGFR 2rgp -ESR1 1sj0 -ESR2 2fsz -FA10 3kl6 -FA7 1w7x -FABP4 2nnq -FAK1 3bz3 -FGFR1 3c4f -FKB1A 1j4h -FNTA 3e37 -FPPS 1zw5 -GCR 3bqd -GLCM 2v3f -GRIA2 3kgc -GRIK1 1vso -HDAC2 3max -HDAC8 3f07 -HIVINT 3nf7 -HIVPR 1xl2 -HIVRT 3lan -HMDH 3ccw -HS90A 1uyg -HXK4 3f9m -IGF1R 2oj9 -INHA 4trj -INHA_obsolete 2h7l -ITAL 2ica -JAK2 3lpb -KIF11 3cjo -KIT 3g0e -KITH 2b8t -KPCB 2i0e -LCK 2of2 -LKHA4 3chp -MAPK2 3m2w -MCR 2aa2 -MET 3lq8 -MK01 2ojg -MK10 2zdt -MK14 2qd9 -MMP13 830c -MP2K1 3eqh -NOS1 1qw6 -NRAM 1b9v -PA2GA 1kvo -PARP1 3l3m -PDE5A 1udt -PGH1 2oyu -PGH2 3ln1 -PLK1 2owb -PNPH 3bgs -PPARA 2p54 -PPARD 2znp -PPARG 2gtk -PRGR 3kba -PTN1 2azr -PUR2 1njs -PYGM 1c8k -PYRD 1d3g -RENI 3g6z -ROCK1 2etr -RXRA 1mv9 -SAHH 1li4 -SRC 3el8 -TGFR1 3hmm -THB 1q4x -THRB 1ype -TRY1 2ayw -TRYB1 2zec -TYSY 1syn -UROK 1sqt -VGFR2 2p2i -WEE1 3biz -XIAP 3hl5 diff --git a/moad.ipynb b/moad.ipynb deleted file mode 100644 index bfe9b2f0b57b84846f6d2ab0cdddbbcc7126272b..0000000000000000000000000000000000000000 --- a/moad.ipynb +++ /dev/null @@ -1,880 +0,0 @@ -{ - "cells": [ - { - "cell_type": "code", - "execution_count": 4, - "id": "c47a32d8-c857-41de-a70a-cec48046df12", - "metadata": {}, - "outputs": [], - "source": [ - "import pandas as pd" - ] - }, - { - "cell_type": "code", - "execution_count": 2, - "id": "e0c6bd53-3417-44bd-b1b4-81802b37fbfc", - "metadata": {}, - "outputs": [], - "source": [ - "df = pd.read_csv('binding_moad/every.csv',header=None,skiprows=2)\n", - "df = df.rename(columns={2:'pdb',3: 'ligand_name', 4: 'ligand_valid', 5: 'affinity_quantity',\n", - " 7: 'affinity_val', 8: 'affinity_unit', 9:'smiles'})\n", - "#df = df[df['ligand_valid']!='invalid'].copy()" - ] - }, - { - "cell_type": "code", - "execution_count": 3, - "id": "a4a7384f-8068-43e8-add7-c498aafe61c9", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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01pdbligand_nameligand_validaffinity_quantity6affinity_valaffinity_unitsmiles10
0NaNNaNNaNHAE:C:989validNaNNaNNaNNaNCC(=O)NONaN
1NaNNaNNaNNI:C:574Part of ProteinNaNNaNNaNNaN[Ni+2]NaN
2NaNNaNNaNNI:C:575Part of ProteinNaNNaNNaNNaN[Ni+2]NaN
3NaNFamily. Representative Entry is6H8JNaNNaNNaNNaNNaNNaNNaNNaN
4NaNNaNNaNSO4:C:611invalidNaNNaNNaNNaN[O-]S(=O)(=O)[O-]NaN
....................................
306520NaNNaNNaNCA:D:1950Part of ProteinNaNNaNNaNNaN[Ca+2]NaN
306521NaNNaNNaNNGA NAG:F:1validKa=5910.0M^-1NaNNaN
306522NaNNaNNaNNGA NAG:E:1validKa=5910.0M^-1NaNNaN
306523NaNNaNNaNNGA NAG:H:1validKa=5910.0M^-1NaNNaN
306524NaNNaNNaNA2G NAG:G:1invalidNaNNaNNaNNaNNaNNaN
\n", - "

306525 rows × 11 columns

\n", - "
" - ], - "text/plain": [ - " 0 1 pdb ligand_name \\\n", - "0 NaN NaN NaN HAE:C:989 \n", - "1 NaN NaN NaN NI:C:574 \n", - "2 NaN NaN NaN NI:C:575 \n", - "3 NaN Family. Representative Entry is 6H8J NaN \n", - "4 NaN NaN NaN SO4:C:611 \n", - "... ... ... ... ... \n", - "306520 NaN NaN NaN CA:D:1950 \n", - "306521 NaN NaN NaN NGA NAG:F:1 \n", - "306522 NaN NaN NaN NGA NAG:E:1 \n", - "306523 NaN NaN NaN NGA NAG:H:1 \n", - "306524 NaN NaN NaN A2G NAG:G:1 \n", - "\n", - " ligand_valid affinity_quantity 6 affinity_val affinity_unit \\\n", - "0 valid NaN NaN NaN NaN \n", - "1 Part of Protein NaN NaN NaN NaN \n", - "2 Part of Protein NaN NaN NaN NaN \n", - "3 NaN NaN NaN NaN NaN \n", - "4 invalid NaN NaN NaN NaN \n", - "... ... ... ... ... ... \n", - "306520 Part of Protein NaN NaN NaN NaN \n", - "306521 valid Ka = 5910.0 M^-1 \n", - "306522 valid Ka = 5910.0 M^-1 \n", - "306523 valid Ka = 5910.0 M^-1 \n", - "306524 invalid NaN NaN NaN NaN \n", - "\n", - " smiles 10 \n", - "0 CC(=O)NO NaN \n", - "1 [Ni+2] NaN \n", - "2 [Ni+2] NaN \n", - "3 NaN NaN \n", - "4 [O-]S(=O)(=O)[O-] NaN \n", - "... ... .. \n", - "306520 [Ca+2] NaN \n", - "306521 NaN NaN \n", - "306522 NaN NaN \n", - "306523 NaN NaN \n", - "306524 NaN NaN \n", - "\n", - "[306525 rows x 11 columns]" - ] - }, - "execution_count": 3, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df" - ] - }, - { - "cell_type": "code", - "execution_count": 3, - "id": "e40b1ddc-9a98-4a3b-b8a6-45e3940a3ea2", - "metadata": {}, - "outputs": [], - "source": [ - "df['is_sep'] = df[1] == 'Family. Representative Entry is '" - ] - }, - { - "cell_type": "code", - "execution_count": 4, - "id": "4f00a0d1-78db-4f32-9d12-5e035b70ef98", - "metadata": {}, - "outputs": [], - "source": [ - "df['cum_sum'] = df['is_sep'].cumsum()" - ] - }, - { - "cell_type": "code", - "execution_count": 7, - "id": "ebaeb749-656e-4b92-8dbd-2e29eefdcad5", - "metadata": {}, - "outputs": [], - "source": [ - "quantities = ['ki','kd','ka','k1/2','kb','ic50','ec50']" - ] - }, - { - "cell_type": "code", - "execution_count": 8, - "id": "52c0c66c-1eb0-415b-b019-bc77419ccbd7", - "metadata": {}, - "outputs": [], - "source": [ - "from pint import UnitRegistry\n", - "ureg = UnitRegistry()\n", - "\n", - "def to_uM(affinity_unit):\n", - " try:\n", - " val = ureg(str(affinity_unit[0])+str(affinity_unit[1]))\n", - " return val.m_as(ureg.uM)\n", - " except Exception:\n", - " pass\n", - " \n", - " try:\n", - " val = ureg(str(affinity_unit[0])+str(affinity_unit[1]))\n", - " return 1/val.m_as(1/ureg.uM)\n", - " except Exception:\n", - " pass" - ] - }, - { - "cell_type": "code", - "execution_count": 9, - "id": "e5b4dd41-1389-408d-bee6-6dbeefc1d5c7", - "metadata": {}, - "outputs": [], - "source": [ - "groupby = df.groupby('cum_sum')" - ] - }, - { - "cell_type": "code", - "execution_count": 10, - "id": "61b8276c-54fe-4989-af5f-723994e1df7e", - "metadata": {}, - "outputs": [], - "source": [ - "def group(df):\n", - " pdb = df[df['is_sep']]['pdb'].values\n", - " if len(pdb) > 0:\n", - " pdb = pdb[0]\n", - " df['pdb_ref'] = pdb\n", - " return df[df['ligand_valid']=='valid']\n", - "df_expand = groupby.apply(group).reset_index(drop=True)" - ] - }, - { - "cell_type": "code", - "execution_count": 11, - "id": "342c8ef3-6808-471b-baa4-f9bdc7f6e8d6", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "88806" - ] - }, - "execution_count": 11, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_expand)" - ] - }, - { - "cell_type": "code", - "execution_count": 12, - "id": "8bb2dfac-5f11-455c-9dee-3607b47b4232", - "metadata": {}, - "outputs": [], - "source": [ - "df_expand['affinity_uM'] = df_expand[['affinity_val','affinity_unit']].apply(to_uM,axis=1)" - ] - }, - { - "cell_type": "code", - "execution_count": 13, - "id": "b5c0fa42-b595-4b96-b2d5-57f0031427dc", - "metadata": {}, - "outputs": [], - "source": [ - "df_filter = df_expand[df_expand['affinity_quantity'].str.lower().isin(quantities)]" - ] - }, - { - "cell_type": "code", - "execution_count": 14, - "id": "27c4865b-5337-48e0-9be7-a913b31cfae1", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "88806" - ] - }, - "execution_count": 14, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_expand)" - ] - }, - { - "cell_type": "code", - "execution_count": 15, - "id": "f3daf4ad-0205-48c0-8c38-36aa4eb561e0", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "25490" - ] - }, - "execution_count": 15, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_filter)" - ] - }, - { - "cell_type": "code", - "execution_count": 23, - "id": "0dc39f62-5b18-4a86-9a44-17d1925da2ad", - "metadata": {}, - "outputs": [], - "source": [ - "df_complex = pd.read_parquet('data/moad_complex.parquet')\n", - "df_complex['name'] = df_complex['name'].str.upper()" - ] - }, - { - "cell_type": "code", - "execution_count": 15, - "id": "719d147f-75eb-4ead-a54f-4b448a62a9a0", - "metadata": {}, - "outputs": [], - "source": [] - }, - { - "cell_type": "code", - "execution_count": 24, - "id": "6d158a41-64c6-4fa2-92d5-562aa11e8924", - "metadata": {}, - "outputs": [], - "source": [ - "df_all = df_filter.merge(df_complex,left_on='pdb_ref',right_on='name')" - ] - }, - { - "cell_type": "code", - "execution_count": 25, - "id": "901fe6c6-dc8c-4ce4-82c6-1fb0b718287a", - "metadata": {}, - "outputs": [], - "source": [ - "df_all = df_all[~df_all['affinity_val'].isnull()]" - ] - }, - { - "cell_type": "code", - "execution_count": 26, - "id": "383f9a1c-ffc6-43da-ac5a-5bcb815be28b", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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01pdbligand_nameligand_validaffinity_quantity6affinity_valaffinity_unitsmiles10is_sepcum_sumpdb_refaffinity_uMnameseq
0NaNNaNNaN2PA:C:613validKi=0.62nMNP(=O)(N)ONaNFalse16H8J0.0006206H8JNYIVPGEYRVAEGEIEINAGREKTTIRVSNTGDRPIQVGSHIHFVE...
1NaNNaNNaNHAE:C:800validKi=2.60uMCC(=O)NONaNFalse16H8J2.6000006H8JNYIVPGEYRVAEGEIEINAGREKTTIRVSNTGDRPIQVGSHIHFVE...
2NaNNaNNaN43W:A:902validic50=580.00nMC#CCCOP(=O)(O)OP(=O)(O)ONaNFalse24S3F0.5800004S3FMEGMRRPTPTVYVGRVPIGGAHPIAVQSMTNTPTRDVEATTAQVLE...
3NaNNaNNaN0CG:A:902validic50=770.00nMC#CCOP(=O)(O)OP(=O)(O)ONaNFalse24S3F0.7700004S3FMEGMRRPTPTVYVGRVPIGGAHPIAVQSMTNTPTRDVEATTAQVLE...
4NaNNaNNaNADN:A:901validKd=15.00uMc1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3...NaNFalse52GL015.0000002GL0MTDMSIKFELIDVPIPQGTNVIIGQAHFIKTVEDLYEALVTSVPGV...
......................................................
25420NaNNaNNaNMAN NAG:G:1validKa=7860.00M^-1NaNNaNFalse104992WDB127.2264632WDBMGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...
25421NaNNaNNaNMAN NAG:F:1validKa=7860.00M^-1NaNNaNFalse104992WDB127.2264632WDBMGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...
25422NaNNaNNaNNGA NAG:F:1validKa=5910.00M^-1NaNNaNFalse104992WDB169.2047382WDBMGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...
25423NaNNaNNaNNGA NAG:E:1validKa=5910.00M^-1NaNNaNFalse104992WDB169.2047382WDBMGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...
25424NaNNaNNaNNGA NAG:H:1validKa=5910.00M^-1NaNNaNFalse104992WDB169.2047382WDBMGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG...
\n", - "

25425 rows × 17 columns

\n", - "
" - ], - "text/plain": [ - " 0 1 pdb ligand_name ligand_valid affinity_quantity 6 \\\n", - "0 NaN NaN NaN 2PA:C:613 valid Ki = \n", - "1 NaN NaN NaN HAE:C:800 valid Ki = \n", - "2 NaN NaN NaN 43W:A:902 valid ic50 = \n", - "3 NaN NaN NaN 0CG:A:902 valid ic50 = \n", - "4 NaN NaN NaN ADN:A:901 valid Kd = \n", - "... ... ... ... ... ... ... .. \n", - "25420 NaN NaN NaN MAN NAG:G:1 valid Ka = \n", - "25421 NaN NaN NaN MAN NAG:F:1 valid Ka = \n", - "25422 NaN NaN NaN NGA NAG:F:1 valid Ka = \n", - "25423 NaN NaN NaN NGA NAG:E:1 valid Ka = \n", - "25424 NaN NaN NaN NGA NAG:H:1 valid Ka = \n", - "\n", - " affinity_val affinity_unit \\\n", - "0 0.62 nM \n", - "1 2.60 uM \n", - "2 580.00 nM \n", - "3 770.00 nM \n", - "4 15.00 uM \n", - "... ... ... \n", - "25420 7860.00 M^-1 \n", - "25421 7860.00 M^-1 \n", - "25422 5910.00 M^-1 \n", - "25423 5910.00 M^-1 \n", - "25424 5910.00 M^-1 \n", - "\n", - " smiles 10 is_sep cum_sum \\\n", - "0 NP(=O)(N)O NaN False 1 \n", - "1 CC(=O)NO NaN False 1 \n", - "2 C#CCCOP(=O)(O)OP(=O)(O)O NaN False 2 \n", - "3 C#CCOP(=O)(O)OP(=O)(O)O NaN False 2 \n", - "4 c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3... NaN False 5 \n", - "... ... .. ... ... \n", - "25420 NaN NaN False 10499 \n", - "25421 NaN NaN False 10499 \n", - "25422 NaN NaN False 10499 \n", - "25423 NaN NaN False 10499 \n", - "25424 NaN NaN False 10499 \n", - "\n", - " pdb_ref affinity_uM name \\\n", - "0 6H8J 0.000620 6H8J \n", - "1 6H8J 2.600000 6H8J \n", - "2 4S3F 0.580000 4S3F \n", - "3 4S3F 0.770000 4S3F \n", - "4 2GL0 15.000000 2GL0 \n", - "... ... ... ... \n", - "25420 2WDB 127.226463 2WDB \n", - "25421 2WDB 127.226463 2WDB \n", - "25422 2WDB 169.204738 2WDB \n", - "25423 2WDB 169.204738 2WDB \n", - "25424 2WDB 169.204738 2WDB \n", - "\n", - " seq \n", - "0 NYIVPGEYRVAEGEIEINAGREKTTIRVSNTGDRPIQVGSHIHFVE... \n", - "1 NYIVPGEYRVAEGEIEINAGREKTTIRVSNTGDRPIQVGSHIHFVE... \n", - "2 MEGMRRPTPTVYVGRVPIGGAHPIAVQSMTNTPTRDVEATTAQVLE... \n", - "3 MEGMRRPTPTVYVGRVPIGGAHPIAVQSMTNTPTRDVEATTAQVLE... \n", - "4 MTDMSIKFELIDVPIPQGTNVIIGQAHFIKTVEDLYEALVTSVPGV... \n", - "... ... \n", - "25420 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "25421 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "25422 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "25423 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "25424 MGSSHHHHHHSSGLVPRGSHMASNPSLIRSESWQVYEGNEANLLDG... \n", - "\n", - "[25425 rows x 17 columns]" - ] - }, - "execution_count": 26, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_all" - ] - }, - { - "cell_type": "code", - "execution_count": 27, - "id": "bebc962b-10f7-478c-8e23-e2d3722e875c", - "metadata": {}, - "outputs": [], - "source": [ - "df_all[['pdb','ligand_name','smiles','name','affinity_uM','seq']].to_parquet('data/moad.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 5, - "id": "49a160d6-4599-488a-ba02-a65a79535f38", - "metadata": {}, - "outputs": [], - "source": [ - "df_all = pd.read_parquet('data/moad.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "bebcbe84-fa6d-4e39-bd26-40ed173e0e67", - "metadata": {}, - "outputs": [], - "source": [] - } - ], - "metadata": { - "kernelspec": { - "display_name": "Python 3", - "language": "python", - "name": "python3" - }, - "language_info": { - "codemirror_mode": { - "name": "ipython", - "version": 3 - }, - "file_extension": ".py", - "mimetype": "text/x-python", - "name": "python", - "nbconvert_exporter": "python", - "pygments_lexer": "ipython3", - "version": "3.9.4" - } - }, - "nbformat": 4, - "nbformat_minor": 5 -} diff --git a/moad.py b/moad.py deleted file mode 100644 index e058244e8eff53fd40aa7e9211d2526ccb193050..0000000000000000000000000000000000000000 --- a/moad.py +++ /dev/null @@ -1,32 +0,0 @@ -from mpi4py import MPI -from mpi4py.futures import MPICommExecutor - -from openbabel import pybel -from Bio import SeqIO - -import os -def parse_complex(fn): - try: - name = os.path.basename(fn).split('.')[0] - print(name) - seq = str(next(SeqIO.parse(fn, "pdb-seqres")).seq) - return name, seq - except: - return None - - -if __name__ == '__main__': - import glob - - filenames = glob.glob('binding_moad/BindingMOAD_2020/*.bio1') - comm = MPI.COMM_WORLD - with MPICommExecutor(comm, root=0) as executor: - if executor is not None: - result = executor.map(parse_complex, filenames) - result = list(result) - names = [r[0] for r in result if r is not None] - seqs = [r[1] for r in result if r is not None] - - import pandas as pd - df = pd.DataFrame({'name': names, 'seq': seqs}) - df.to_parquet('data/moad_complex.parquet') diff --git a/moad.slurm b/moad.slurm deleted file mode 100644 index d61ca477541fbc16b56ca542fac7c03f33135a25..0000000000000000000000000000000000000000 --- a/moad.slurm +++ /dev/null @@ -1,10 +0,0 @@ -#!/bin/bash -#SBATCH -J preprocess_moad -#SBATCH -p batch -#SBATCH -A BIP214 -#SBATCH -t 3:00:00 -#SBATCH -N 12 -#SBATCH --ntasks-per-node=8 - -export PYTHONUNBUFFERED=1 -srun python moad.py diff --git a/pdbbind.ipynb b/pdbbind.ipynb deleted file mode 100644 index c63cf95985d9ddbc3fa809dea55ce716f6763b02..0000000000000000000000000000000000000000 --- a/pdbbind.ipynb +++ /dev/null @@ -1,383 +0,0 @@ -{ - "cells": [ - { - "cell_type": "markdown", - "id": "834aeced-c3c5-42a0-bad1-41e009dd86ee", - "metadata": {}, - "source": [ - "### Preprocessing" - ] - }, - { - "cell_type": "code", - "execution_count": 1, - "id": "86476f6e-802a-463b-a1b0-2ae228bb92af", - "metadata": {}, - "outputs": [], - "source": [ - "import pandas as pd" - ] - }, - { - "cell_type": "code", - "execution_count": 12, - "id": "9b2be11c-f4bb-4107-af49-abd78052afcf", - "metadata": {}, - "outputs": [], - "source": [ - "df = pd.read_table('pdbbind/data/index/INDEX_general_PL_data.2020',skiprows=4,sep=r'\\s+',usecols=[0,4]).drop(0)\n", - "df = df.rename(columns={'#': 'name','release': 'affinity'})\n", - "df_refined = pd.read_table('pdbbind/data/index/INDEX_refined_data.2020',skiprows=4,sep=r'\\s+',usecols=[0,4]).drop(0)\n", - "df_refined = df_refined.rename(columns={'#': 'name','release': 'affinity'})\n", - "df = pd.concat([df,df_refined])" - ] - }, - { - "cell_type": "code", - "execution_count": 13, - "id": "68983ab8-bf11-4ed6-ba06-f962dbdc077e", - "metadata": {}, - "outputs": [], - "source": [ - "quantities = ['ki','kd','ka','k1/2','kb','ic50','ec50']" - ] - }, - { - "cell_type": "code", - "execution_count": 14, - "id": "3acbca3c-9c0b-43a1-a45e-331bf153bcfa", - "metadata": {}, - "outputs": [], - "source": [ - "from pint import UnitRegistry\n", - "ureg = UnitRegistry()\n", - "\n", - "def to_uM(affinity):\n", - " val = ureg(affinity)\n", - " try:\n", - " return val.m_as(ureg.uM)\n", - " except Exception:\n", - " pass\n", - " \n", - " try:\n", - " return 1/val.m_as(1/ureg.uM)\n", - " except Exception:\n", - " pass" - ] - }, - { - "cell_type": "code", - "execution_count": 15, - "id": "58e5748b-2cea-43ff-ab51-85a5021bd50b", - "metadata": {}, - "outputs": [], - "source": [ - "df['affinity_uM'] = df['affinity'].str.split('[=\\~><]').str[1].apply(to_uM)\n", - "df['affinity_quantity'] = df['affinity'].str.split('[=\\~><]').str[0]" - ] - }, - { - "cell_type": "code", - "execution_count": 16, - "id": "d92f0004-68c1-4487-94b9-56b4fd598de4", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "" - ] - }, - "execution_count": 16, - "metadata": {}, - "output_type": "execute_result" - }, - { - "data": { - "image/png": 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" - ] - }, - "metadata": { - "needs_background": "light" - }, - "output_type": "display_data" - } - ], - "source": [ - "df['affinity_quantity'].hist()" - ] - }, - { - "cell_type": "code", - "execution_count": 17, - "id": "aa358835-55f3-4551-9217-e76a15de4fe8", - "metadata": {}, - "outputs": [], - "source": [ - "df_filter = df[df['affinity_quantity'].str.lower().isin(quantities)]" - ] - }, - { - "cell_type": "code", - "execution_count": 18, - "id": "d6dda488-f709-4fe7-b372-080042cf7c66", - "metadata": {}, - "outputs": [], - "source": [ - "df_complex = pd.read_parquet('data/pdbbind_complex.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 20, - "id": "df7929e3-c7fd-4e1b-a165-92f8d53b9011", - "metadata": {}, - "outputs": [], - "source": [ - "df_all = df_complex.merge(df_filter,on='name').drop('affinity',axis=1)" - ] - }, - { - "cell_type": "code", - "execution_count": 21, - "id": "41711825-b110-472b-a9f3-2eccc5afbfd9", - "metadata": {}, - "outputs": [ - { - "data": { - "text/html": [ - "
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33t4pAAPFDKSKNVAQSIDQLIGQTPALYLNKLNNTKAKVVLKMECENPM...OC[C@@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)NC(=O)...6.43000Kd
46oyzYITFRSFTAVLIAFFLTLVLSPSFINRLRKIQRKKYTPTMGGIVIL...CO[C@@H]1[C@H](O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1...0.18500IC50
..................
247544j46GTIYPRNPAMYSEEARLKSFQNWPDYAHLTPRELASAGLYYTGIGD...CC[C@@H]([C@@H](C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)...5.24000Ki
247552c80DHIKVIYFNGRGRAESIRMTLVAAGVNYEDERISFQDWPKIKPTIP...CCCCCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(...4.70000Kd
247562c80DHIKVIYFNGRGRAESIRMTLVAAGVNYEDERISFQDWPKIKPTIP...CCCCCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(...4.70000Kd
247575wl0NDDIDQSLIIAARNIVRRASVSADPLASLLEMCHSTQIGGTRMVDI...OC(=O)[C@H]1[C@@H]2CC[C@H]([C@@H]1Nc1nc(ncc1F)...0.00067Kd
247585wl0NDDIDQSLIIAARNIVRRASVSADPLASLLEMCHSTQIGGTRMVDI...OC(=O)[C@H]1[C@@H]2CC[C@H]([C@@H]1Nc1nc(ncc1F)...0.00067Kd
\n", - "

24759 rows × 5 columns

\n", - "
" - ], - "text/plain": [ - " name seq \\\n", - "0 2lbv MTVPDRSEIAGKWYVVALASNTEFFLREKDKMKMAMARISFLGEDE... \n", - "1 1lt6 APQTITELCSEYRNTQIYTINDKILSYTESMAGKREMVIITFKSGE... \n", - "2 4lwi VETFAFQAEIAQLMSLIINTFYSNKEIFLRELISNSSDALDKIRYE... \n", - "3 3t4p AAPFDKSKNVAQSIDQLIGQTPALYLNKLNNTKAKVVLKMECENPM... \n", - "4 6oyz YITFRSFTAVLIAFFLTLVLSPSFINRLRKIQRKKYTPTMGGIVIL... \n", - "... ... ... \n", - "24754 4j46 GTIYPRNPAMYSEEARLKSFQNWPDYAHLTPRELASAGLYYTGIGD... \n", - "24755 2c80 DHIKVIYFNGRGRAESIRMTLVAAGVNYEDERISFQDWPKIKPTIP... \n", - "24756 2c80 DHIKVIYFNGRGRAESIRMTLVAAGVNYEDERISFQDWPKIKPTIP... \n", - "24757 5wl0 NDDIDQSLIIAARNIVRRASVSADPLASLLEMCHSTQIGGTRMVDI... \n", - "24758 5wl0 NDDIDQSLIIAARNIVRRASVSADPLASLLEMCHSTQIGGTRMVDI... \n", - "\n", - " smiles affinity_uM \\\n", - "0 CCCCCCCCCCCCCCCCCCCC(=O)O 0.02600 \n", - "1 OC[C@H]1O[C@H](Oc2cccc(c2)N(=O)=O)[C@@H]([C@H]... 500.00000 \n", - "2 COc1ccc(cc1)c1c(onc1c1cc(C(C)C)c(cc1O)O)NC(=O)... 0.02300 \n", - "3 OC[C@@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)NC(=O)... 6.43000 \n", - "4 CO[C@@H]1[C@H](O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1... 0.18500 \n", - "... ... ... \n", - "24754 CC[C@@H]([C@@H](C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)... 5.24000 \n", - "24755 CCCCCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(... 4.70000 \n", - "24756 CCCCCCSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(... 4.70000 \n", - "24757 OC(=O)[C@H]1[C@@H]2CC[C@H]([C@@H]1Nc1nc(ncc1F)... 0.00067 \n", - "24758 OC(=O)[C@H]1[C@@H]2CC[C@H]([C@@H]1Nc1nc(ncc1F)... 0.00067 \n", - "\n", - " affinity_quantity \n", - "0 Kd \n", - "1 IC50 \n", - "2 IC50 \n", - "3 Kd \n", - "4 IC50 \n", - "... ... \n", - "24754 Ki \n", - "24755 Kd \n", - "24756 Kd \n", - "24757 Kd \n", - "24758 Kd \n", - "\n", - "[24759 rows x 5 columns]" - ] - }, - "execution_count": 21, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "df_all" - ] - }, - { - "cell_type": "code", - "execution_count": 53, - "id": "4d105c42-0d11-49db-9012-52fafc9cd299", - "metadata": {}, - "outputs": [], - "source": [ - "df_all.to_parquet('data/pdbbind.parquet')" - ] - }, - { - "cell_type": "code", - "execution_count": 54, - "id": "2955b056-26dd-45fa-8d74-f17661253a9a", - "metadata": {}, - "outputs": [ - { - "data": { - "text/plain": [ - "24759" - ] - }, - "execution_count": 54, - "metadata": {}, - "output_type": "execute_result" - } - ], - "source": [ - "len(df_all)" - ] - }, - { - "cell_type": "code", - "execution_count": null, - "id": "ed3fe035-6035-4d39-b072-d12dc0a95857", - "metadata": {}, - "outputs": [], - "source": [] - } - ], - "metadata": { - "kernelspec": { - "display_name": "Python 3", - "language": "python", - "name": "python3" - }, - "language_info": { - "codemirror_mode": { - "name": "ipython", - "version": 3 - }, - "file_extension": ".py", - "mimetype": "text/x-python", - "name": "python", - "nbconvert_exporter": "python", - "pygments_lexer": "ipython3", - "version": "3.9.4" - } - }, - "nbformat": 4, - "nbformat_minor": 5 -} diff --git a/pdbbind.py b/pdbbind.py deleted file mode 100644 index b471da8d53963541ff5b503be0a544bbc6b9bc36..0000000000000000000000000000000000000000 --- a/pdbbind.py +++ /dev/null @@ -1,108 +0,0 @@ -from mpi4py import MPI -from mpi4py.futures import MPICommExecutor - -import warnings -from Bio.PDB import PDBParser, PPBuilder, CaPPBuilder -from Bio.PDB.NeighborSearch import NeighborSearch -from Bio.PDB.Selection import unfold_entities - -import numpy as np -import dask.array as da - -from rdkit import Chem - -import os -import re - -# all punctuation -punctuation_regex = r"""(\(|\)|\.|=|#|-|\+|\\|\/|:|~|@|\?|>>?|\*|\$|\%[0-9]{2}|[0-9])""" - -# tokenization regex (Schwaller) -molecule_regex = r"""(\[[^\]]+]|Br?|Cl?|N|O|S|P|F|I|b|c|n|o|s|p|\(|\)|\.|=|#|-|\+|\\|\/|:|~|@|\?|>>?|\*|\$|\%[0-9]{2}|[0-9])""" - -cutoff = 5 -max_seq = 2048 -max_smiles = 512 -chunk_size = '1G' - -def parse_complex(fn): - try: - name = os.path.basename(fn) - - # parse protein sequence and coordinates - parser = PDBParser() - with warnings.catch_warnings(): - warnings.simplefilter("ignore") - structure = parser.get_structure('protein',fn+'/'+name+'_protein.pdb') - -# ppb = PPBuilder() - ppb = CaPPBuilder() - seq = [] - for pp in ppb.build_peptides(structure): - seq.append(str(pp.get_sequence())) - seq = ''.join(seq) - - # parse ligand, convert to SMILES and map atoms - suppl = Chem.SDMolSupplier(fn+'/'+name+'_ligand.sdf') - mol = next(suppl) - smi = Chem.MolToSmiles(mol) - - # position of atoms in SMILES (not counting punctuation) - atom_order = mol.GetProp("_smilesAtomOutputOrder") - atom_order = [int(s) for s in list(filter(None,re.sub(r'[\[\]]','',mol.GetProp("_smilesAtomOutputOrder")).split(',')))] - - # tokenize the SMILES - tokens = list(filter(None, re.split(molecule_regex, smi))) - - # remove punctuation - masked_tokens = [re.sub(punctuation_regex,'',s) for s in tokens] - - k = 0 - token_pos = [] - token_id = [] - for i,token in enumerate(masked_tokens): - if token != '': - token_pos.append(tuple(mol.GetConformer().GetAtomPosition(atom_order[k]))) - token_id.append(i) - k += 1 - - # query protein for ligand contacts - atoms = unfold_entities(structure, 'A') - neighbor_search = NeighborSearch(atoms) - - close_residues = [neighbor_search.search(center=t, level='R', radius=cutoff) for t in token_pos] - residue_id = [[c.get_id()[1]-1 for c in query] for query in close_residues] # zero-based - - # contact map - contact_map = np.zeros((max_seq, max_smiles),dtype=np.float32) - - for query,t in zip(residue_id,token_id): - for r in query: - contact_map[r,t] = 1 - - return name, seq, smi, contact_map - except Exception as e: - print(e) - return None - - -if __name__ == '__main__': - import glob - - filenames = glob.glob('data/pdbbind/v2020-other-PL/*') - filenames.extend(glob.glob('data/pdbbind/refined-set/*')) - comm = MPI.COMM_WORLD - with MPICommExecutor(comm, root=0) as executor: - if executor is not None: - result = executor.map(parse_complex, filenames) - result = list(result) - names = [r[0] for r in result if r is not None] - seqs = [r[1] for r in result if r is not None] - all_smiles = [r[2] for r in result if r is not None] - all_contacts = [r[3] for r in result if r is not None] - - import pandas as pd - df = pd.DataFrame({'name': names, 'seq': seqs, 'smiles': all_smiles}) - all_contacts = da.from_array(all_contacts, chunks=chunk_size) - da.to_npy_stack('data/pdbbind_contacts/', all_contacts) - df.to_parquet('data/pdbbind_complex.parquet') diff --git a/pdbbind.slurm b/pdbbind.slurm deleted file mode 100644 index 72b0c424e629a0d3d98c7868f539de2ae8cc93dc..0000000000000000000000000000000000000000 --- a/pdbbind.slurm +++ /dev/null @@ -1,9 +0,0 @@ -#!/bin/bash -#SBATCH -J preprocess_pdbbind -#SBATCH -p gpu -#SBATCH -A STF006 -#SBATCH -t 3:00:00 -#SBATCH -N 2 -#SBATCH --ntasks-per-node=16 - -srun python pdbbind.py diff --git a/pdbbind_contacts.npy b/pdbbind_contacts.npy deleted file mode 100644 index e69de29bb2d1d6434b8b29ae775ad8c2e48c5391..0000000000000000000000000000000000000000 diff --git a/requirements.txt b/requirements.txt deleted file mode 100644 index 57393ba2f947870bcad565949efdbfae7497f9f0..0000000000000000000000000000000000000000 --- a/requirements.txt +++ /dev/null @@ -1,6 +0,0 @@ -mpi4py -rdkit -openbabel -pyarrow -huggingface_hub -datasets