{ "cells": [ { "cell_type": "code", "execution_count": 13, "metadata": { "collapsed": true }, "outputs": [], "source": [ "# aim: to retrieve compounds from chembl tested against a target\n", "# starting point: UNIPROT ID of target (from e.g. www.rcsb.org)" ] }, { "cell_type": "code", "execution_count": 14, "metadata": { "collapsed": true }, "outputs": [], "source": [ "# some general settngs\n", "import json\n", "import warnings\n", "import logging" ] }, { "cell_type": "code", "execution_count": 15, "metadata": { "collapsed": true }, "outputs": [], "source": [ "# loading chembl package, creating chembl client\n", "import chembl_webresource_client\n", "from chembl_webresource_client import *\n", "from chembl_webresource_client.settings import Settings\n", "from chembl_webresource_client.new_client import new_client as chembl" ] }, { "cell_type": "code", "execution_count": 16, "metadata": { "collapsed": true }, "outputs": [], "source": [ "chembl.target.set_format('json')" ] }, { "cell_type": "code", "execution_count": 17, "metadata": { "collapsed": false, "scrolled": false }, "outputs": [ { "name": "stdout", "output_type": "stream", "text": [ "['__class__', '__delattr__', '__dict__', '__dir__', '__doc__', '__eq__', '__format__', '__ge__', '__getattribute__', '__gt__', '__hash__', '__init__', '__init_subclass__', '__le__', '__lt__', '__module__', '__ne__', '__new__', '__reduce__', '__reduce_ex__', '__repr__', '__setattr__', '__sizeof__', '__str__', '__subclasshook__', '__weakref__', 'activity', 'assay', 'atc_class', 'binding_site', 'biotherapeutic', 'cell_line', 'chembl_id_lookup', 'compound_record', 'compound_structural_alert', 'description', 'document', 'document_similarity', 'document_term', 'drug', 'drug_indication', 'go_slim', 'image', 'mechanism', 'metabolism', 'molecule', 'molecule_form', 'official', 'organism', 'protein_class', 'similarity', 'source', 'substructure', 'target', 'target_component', 'target_prediction', 'target_relation', 'tissue', 'xref_source']\n", "[{'cross_references': [{'xref_id': 'O43451', 'xref_name': None, 'xref_src': 'canSAR-Target'}, {'xref_id': 'Maltase-glucoamylase', 'xref_name': None, 'xref_src': 'Wikipedia'}], 'organism': 'Homo sapiens', 'pref_name': 'Maltase-glucoamylase', 'species_group_flag': False, 'target_chembl_id': 'CHEMBL2074', 'target_components': [{'accession': 'O43451', 'component_description': 'Maltase-glucoamylase, intestinal', 'component_id': 434, 'component_type': 'PROTEIN', 'relationship': 'SINGLE PROTEIN', 'target_component_synonyms': [{'component_synonym': 'MGA ', 'syn_type': 'GENE_SYMBOL'}, {'component_synonym': 'MGAML', 'syn_type': 'GENE_SYMBOL'}, {'component_synonym': 'MGAM', 'syn_type': 'GENE_SYMBOL'}, {'component_synonym': 'Maltase-glucoamylase, intestinal', 'syn_type': 'UNIPROT'}, {'component_synonym': 'Maltase', 'syn_type': 'UNIPROT'}, {'component_synonym': 'Glucoamylase', 'syn_type': 'UNIPROT'}, {'component_synonym': 'Alpha-glucosidase', 'syn_type': 'UNIPROT'}, {'component_synonym': 'Glucan 1,4-alpha-glucosidase', 'syn_type': 'UNIPROT'}, {'component_synonym': '3.2.1.20', 'syn_type': 'EC_NUMBER'}, {'component_synonym': '3.2.1.3', 'syn_type': 'EC_NUMBER'}]}], 'target_type': 'SINGLE PROTEIN', 'tax_id': 9606}, {'cross_references': [{'xref_id': 'O60706', 'xref_name': None, 'xref_src': 'canSAR-Target'}, {'xref_id': 'ABCC9', 'xref_name': None, 'xref_src': 'Wikipedia'}], 'organism': 'Homo sapiens', 'pref_name': 'Sulfonylurea receptor 2', 'species_group_flag': False, 'target_chembl_id': 'CHEMBL1971', 'target_components': [{'accession': 'O60706', 'component_description': 'ATP-binding cassette sub-family C member 9', 'component_id': 294, 'component_type': 'PROTEIN', 'relationship': 'SINGLE PROTEIN', 'target_component_synonyms': [{'component_synonym': 'SUR2', 'syn_type': 'GENE_SYMBOL'}, {'component_synonym': 'ABCC9', 'syn_type': 'GENE_SYMBOL'}, {'component_synonym': 'ATP-binding cassette sub-family C member 9', 'syn_type': 'UNIPROT'}, {'component_synonym': 'Sulfonylurea receptor 2', 'syn_type': 'UNIPROT'}]}], 'target_type': 'SINGLE PROTEIN', 'tax_id': 9606}, {'cross_references': [{'xref_id': 'CGMP-specific_phosphodiesterase_type_5', 'xref_name': None, 'xref_src': 'Wikipedia'}], 'organism': 'Homo sapiens', 'pref_name': 'Phosphodiesterase 5A', 'species_group_flag': False, 'target_chembl_id': 'CHEMBL1827', 'target_components': [{'accession': 'O76074', 'component_description': \"cGMP-specific 3',5'-cyclic phosphodiesterase\", 'component_id': 124, 'component_type': 'PROTEIN', 'relationship': 'SINGLE PROTEIN', 'target_component_synonyms': [{'component_synonym': 'PDE5', 'syn_type': 'GENE_SYMBOL'}, {'component_synonym': 'PDE5A', 'syn_type': 'GENE_SYMBOL'}, {'component_synonym': \"cGMP-specific 3',5'-cyclic phosphodiesterase\", 'syn_type': 'UNIPROT'}, {'component_synonym': 'cGMP-binding cGMP-specific phosphodiesterase', 'syn_type': 'UNIPROT'}, {'component_synonym': 'CGB-PDE', 'syn_type': 'UNIPROT'}, {'component_synonym': '3.1.4.35', 'syn_type': 'EC_NUMBER'}]}], 'target_type': 'SINGLE PROTEIN', 'tax_id': 9606}, {'cross_references': [{'xref_id': 'O95180', 'xref_name': None, 'xref_src': 'canSAR-Target'}, {'xref_id': 'CACNA1H', 'xref_name': None, 'xref_src': 'Wikipedia'}], 'organism': 'Homo sapiens', 'pref_name': 'Voltage-gated T-type calcium channel alpha-1H subunit', 'species_group_flag': False, 'target_chembl_id': 'CHEMBL1859', 'target_components': [{'accession': 'O95180', 'component_description': 'Voltage-dependent T-type calcium channel subunit alpha-1H', 'component_id': 167, 'component_type': 'PROTEIN', 'relationship': 'SINGLE PROTEIN', 'target_component_synonyms': [{'component_synonym': 'CACNA1H', 'syn_type': 'GENE_SYMBOL'}, {'component_synonym': 'Voltage-dependent T-type calcium channel subunit alpha-1H', 'syn_type': 'UNIPROT'}, {'component_synonym': 'Low-voltage-activated calcium channel alpha1 3.2 subunit', 'syn_type': 'UNIPROT'}, {'component_synonym': 'Voltage-gated calcium channel subunit alpha Cav3.2', 'syn_type': 'UNIPROT'}]}], 'target_type': 'SINGLE PROTEIN', 'tax_id': 9606}, '...(remaining elements truncated)...']\n", "O43451\n" ] } ], "source": [ "# step 1: finding CHEMBL id of target\n", "# we poke a bit around in the data structure\n", "print(dir(chembl))\n", "print(chembl.target)\n", "print(chembl.target[0]['target_components'][0]['accession'] )" ] }, { "cell_type": "code", "execution_count": 18, "metadata": { "collapsed": false }, "outputs": [ { "name": "stdout", "output_type": "stream", "text": [ "P42684\n", "0\n", "1\n", "2\n", "3\n", "4\n", "5\n", "6\n", "7\n", "8\n", "9\n", "10\n", "11\n", "12\n", "13\n", "14\n", "15\n", "16\n", "17\n", "18\n", "19\n", "20\n", "21\n", "22\n", "23\n", "24\n", "25\n", "26\n", "27\n", "28\n", "29\n", "30\n", "31\n", "32\n", "33\n", "34\n", "35\n", "36\n", "37\n", "38\n", "39\n", "40\n", "41\n", "42\n", "43\n", "44\n", "45\n", "46\n", "47\n", "48\n", "49\n", "50\n", "51\n", "52\n", "53\n", "54\n", "55\n", "56\n", "57\n", "58\n", 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"11507\n", "11508\n", "11509\n", "11510\n", "11511\n", "11512\n", "11513\n", "11514\n", "11515\n", "11516\n", "11517\n", "11518\n", "11519\n", "11520\n", "11521\n", "11522\n", "11523\n", "11524\n", "11525\n", "11526\n", "11527\n", "11528\n", "11529\n", "11530\n", "11531\n", "11532\n", "11533\n", "11534\n", "11535\n", "11536\n", "11537\n", "1\n", "Abelson tyrosine-protein kinase 2 CHEMBL4014\n", "for 4099 targets no accession id was found\n" ] } ], "source": [ "# step 2: we search chembl.target list for items that have our \n", "# uniprot code in chembl.target[]['target_components'][0]['accession'] dictionary\n", "ABL_kinase_uniprotID = \"P42684\"\n", "print(ABL_kinase_uniprotID)\n", "chembl_abl_candidates = []\n", "errorcount = 0\n", "for i in range(len(chembl.target)):\n", " print(i)\n", " try:\n", " if chembl.target[i]['target_components'][0]['accession'] == ABL_kinase_uniprotID:\n", " chembl_abl_candidates.append(chembl.target[i])\n", " except:\n", " errorcount += 1\n", "print(len(chembl_abl_candidates)) \n", "print(chembl_abl_candidates[0]['target_components'][0]['component_description'],\n", " chembl_abl_candidates[0]['target_chembl_id'] )\n", "\n", "print(\"for \" + str(errorcount) + \" targets no accession id was found\") \n", " " ] }, { "cell_type": "code", "execution_count": 19, "metadata": { "collapsed": false }, "outputs": [ { "name": "stdout", "output_type": "stream", "text": [ "[('CHEMBL4014', 'Tyrosine-protein kinase ABL2'), ('CHEMBL2111414', 'Tyrosine-protein kinase ABL')]\n" ] } ], "source": [ "# bingo, the component maescription matches, we have found our CHEMBL id\n", "# this code snippet does a similar job, but returns the CHEMBL id for the ABL family of enzymes as well\n", "chembl_abl_candidates_alt = chembl.target.filter(target_components__accession=ABL_kinase_uniprotID)\n", "print ([(x['target_chembl_id'], x['pref_name']) for x in chembl_abl_candidates_alt])" ] }, { "cell_type": "code", "execution_count": 20, "metadata": { "collapsed": false }, "outputs": [ { "name": "stdout", "output_type": "stream", "text": [ "[{'activity_comment': None, 'activity_id': 31863, 'assay_chembl_id': 'CHEMBL663853', 'assay_description': 'Inhibitory concentration against human DNA topoisomerase II, alpha mediated relaxation of pBR322; no measurable activity', 'assay_type': 'B', 'bao_endpoint': 'BAO_0000190', 'bao_format': 'BAO_0000357', 'bao_label': 'single protein format', 'canonical_smiles': 'o1c(nc2c(cccc12)c3oc4ccccc4n3)c5ccccc5', 'data_validity_comment': None, 'document_chembl_id': 'CHEMBL1137930', 'document_journal': 'Bioorg. Med. Chem. Lett.', 'document_year': 2004, 'ligand_efficiency': None, 'molecule_chembl_id': 'CHEMBL113081', 'parent_molecule_chembl_id': 'CHEMBL113081', 'pchembl_value': None, 'potential_duplicate': False, 'published_relation': '>', 'published_type': 'IC50', 'published_units': 'uM', 'published_value': '100', 'qudt_units': 'http://www.openphacts.org/units/Nanomolar', 'record_id': 206172, 'src_id': 1, 'standard_flag': True, 'standard_relation': '>', 'standard_type': 'IC50', 'standard_units': 'nM', 'standard_value': '100000', 'target_chembl_id': 'CHEMBL1806', 'target_organism': 'Homo sapiens', 'target_pref_name': 'DNA topoisomerase II alpha', 'target_tax_id': '9606', 'uo_units': 'UO_0000065'}, {'activity_comment': None, 'activity_id': 31864, 'assay_chembl_id': 'CHEMBL872937', 'assay_description': 'In vivo inhibitory activity against human Heparanase', 'assay_type': 'B', 'bao_endpoint': 'BAO_0000190', 'bao_format': 'BAO_0000218', 'bao_label': 'organism-based format', 'canonical_smiles': 'Cc1ccc2oc(nc2c1)c3cccc(c3)N4C(=O)c5ccc(cc5C4=O)C(=O)O', 'data_validity_comment': None, 'document_chembl_id': 'CHEMBL1146658', 'document_journal': 'Bioorg. Med. Chem. Lett.', 'document_year': 2004, 'ligand_efficiency': {'bei': '14.06', 'le': '0.26', 'lle': '1.59', 'sei': '5.56'}, 'molecule_chembl_id': 'CHEMBL324340', 'parent_molecule_chembl_id': 'CHEMBL324340', 'pchembl_value': '5.6', 'potential_duplicate': False, 'published_relation': '=', 'published_type': 'IC50', 'published_units': 'uM', 'published_value': '2.5', 'qudt_units': 'http://www.openphacts.org/units/Nanomolar', 'record_id': 208970, 'src_id': 1, 'standard_flag': True, 'standard_relation': '=', 'standard_type': 'IC50', 'standard_units': 'nM', 'standard_value': '2500', 'target_chembl_id': 'CHEMBL3921', 'target_organism': 'Homo sapiens', 'target_pref_name': 'Heparanase', 'target_tax_id': '9606', 'uo_units': 'UO_0000065'}, {'activity_comment': None, 'activity_id': 31865, 'assay_chembl_id': 'CHEMBL693237', 'assay_description': 'In vivo concentration required against angiogenesis in human endothelial cells', 'assay_type': 'F', 'bao_endpoint': 'BAO_0000190', 'bao_format': 'BAO_0000218', 'bao_label': 'organism-based format', 'canonical_smiles': 'Cc1ccc2oc(nc2c1)c3cccc(c3)N4C(=O)c5ccc(cc5C4=O)C(=O)O', 'data_validity_comment': None, 'document_chembl_id': 'CHEMBL1146658', 'document_journal': 'Bioorg. Med. Chem. Lett.', 'document_year': 2004, 'ligand_efficiency': None, 'molecule_chembl_id': 'CHEMBL324340', 'parent_molecule_chembl_id': 'CHEMBL324340', 'pchembl_value': None, 'potential_duplicate': False, 'published_relation': '>', 'published_type': 'IC50', 'published_units': 'uM', 'published_value': '50', 'qudt_units': 'http://www.openphacts.org/units/Nanomolar', 'record_id': 208970, 'src_id': 1, 'standard_flag': True, 'standard_relation': '>', 'standard_type': 'IC50', 'standard_units': 'nM', 'standard_value': '50000', 'target_chembl_id': 'CHEMBL612545', 'target_organism': None, 'target_pref_name': 'Unchecked', 'target_tax_id': None, 'uo_units': 'UO_0000065'}, {'activity_comment': None, 'activity_id': 31866, 'assay_chembl_id': 'CHEMBL872937', 'assay_description': 'In vivo inhibitory activity against human Heparanase', 'assay_type': 'B', 'bao_endpoint': 'BAO_0000190', 'bao_format': 'BAO_0000218', 'bao_label': 'organism-based format', 'canonical_smiles': 'COc1ccc(cc1N2C(=O)c3ccc(cc3C2=O)C(=O)O)c4oc5ccc(cc5n4)c6ccccc6OC', 'data_validity_comment': None, 'document_chembl_id': 'CHEMBL1146658', 'document_journal': 'Bioorg. Med. Chem. Lett.', 'document_year': 2004, 'ligand_efficiency': {'bei': '9.69', 'le': '0.18', 'lle': '0.04', 'sei': '4.23'}, 'molecule_chembl_id': 'CHEMBL109600', 'parent_molecule_chembl_id': 'CHEMBL109600', 'pchembl_value': '5.05', 'potential_duplicate': False, 'published_relation': '=', 'published_type': 'IC50', 'published_units': 'uM', 'published_value': '9', 'qudt_units': 'http://www.openphacts.org/units/Nanomolar', 'record_id': 208987, 'src_id': 1, 'standard_flag': True, 'standard_relation': '=', 'standard_type': 'IC50', 'standard_units': 'nM', 'standard_value': '9000', 'target_chembl_id': 'CHEMBL3921', 'target_organism': 'Homo sapiens', 'target_pref_name': 'Heparanase', 'target_tax_id': '9606', 'uo_units': 'UO_0000065'}, '...(remaining elements truncated)...']\n" ] } ], "source": [ "print(chembl.activity)" ] }, { "cell_type": "code", "execution_count": 21, "metadata": { "collapsed": false }, "outputs": [ { "name": "stdout", "output_type": "stream", "text": [ "[{'activity_comment': 'Not Active', 'activity_id': 1650414, 'assay_chembl_id': 'CHEMBL860899', 'assay_description': 'Average Binding Constant for ABL2; NA=Not Active at 10 uM', 'assay_type': 'B', 'bao_endpoint': 'BAO_0000034', 'bao_format': 'BAO_0000357', 'bao_label': 'single protein format', 'canonical_smiles': 'CS(=O)(=O)CCNCc1oc(cc1)c2ccc3ncnc(Nc4ccc(OCc5cccc(F)c5)c(Cl)c4)c3c2', 'data_validity_comment': None, 'document_chembl_id': 'CHEMBL1144455', 'document_journal': 'Nat. 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Chem.', 'document_year': 2016, 'ligand_efficiency': None, 'molecule_chembl_id': 'CHEMBL3818247', 'parent_molecule_chembl_id': 'CHEMBL3818247', 'pchembl_value': None, 'potential_duplicate': None, 'published_relation': '>', 'published_type': 'IC50', 'published_units': 'nM', 'published_value': '30000', 'qudt_units': 'http://www.openphacts.org/units/Nanomolar', 'record_id': 2784915, 'src_id': 1, 'standard_flag': True, 'standard_relation': '>', 'standard_type': 'IC50', 'standard_units': 'nM', 'standard_value': '30000', 'target_chembl_id': 'CHEMBL4014', 'target_organism': 'Homo sapiens', 'target_pref_name': 'Tyrosine-protein kinase ABL2', 'target_tax_id': '9606', 'uo_units': 'UO_0000065'}, {'activity_comment': None, 'activity_id': 16622192, 'assay_chembl_id': 'CHEMBL3820470', 'assay_description': 'Inhibition of ARG (unknown origin) incubated for 1 hr by spectrophotometric analysis', 'assay_type': 'B', 'bao_endpoint': 'BAO_0000190', 'bao_format': None, 'bao_label': None, 'canonical_smiles': 'CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)n3c4ccccc4c5c6CNC(=O)c6c7c8ccccc8n2c7c35', 'data_validity_comment': None, 'document_chembl_id': 'CHEMBL3817824', 'document_journal': 'Bioorg. Med. Chem.', 'document_year': 2016, 'ligand_efficiency': None, 'molecule_chembl_id': 'CHEMBL388978', 'parent_molecule_chembl_id': 'CHEMBL388978', 'pchembl_value': '7.12', 'potential_duplicate': None, 'published_relation': '=', 'published_type': 'IC50', 'published_units': 'nM', 'published_value': '75.9', 'qudt_units': 'http://www.openphacts.org/units/Nanomolar', 'record_id': 2783100, 'src_id': 1, 'standard_flag': True, 'standard_relation': '=', 'standard_type': 'IC50', 'standard_units': 'nM', 'standard_value': '75.9', 'target_chembl_id': 'CHEMBL4014', 'target_organism': 'Homo sapiens', 'target_pref_name': 'Tyrosine-protein kinase ABL2', 'target_tax_id': '9606', 'uo_units': 'UO_0000065'}]\n" ] } ], "source": [ "# Let's get all measurement for a target\n", "chembl_abl_activities = chembl.activity.filter(target_chembl_id='CHEMBL4014')\n", "print(list(chembl_abl_activities))" ] }, { "cell_type": "code", "execution_count": 22, "metadata": { "collapsed": false }, "outputs": [], "source": [ "import xmltodict" ] }, { "cell_type": "code", "execution_count": 23, "metadata": { "collapsed": false, "scrolled": false }, "outputs": [ { "name": "stdout", "output_type": "stream", "text": [ "14 2\n", "CN1CCN(CC1)c2cc(Nc3cc(C)[nH]n3)nc(Sc4ccc(NC(=O)C5CC5)cc4)n2\n", "CSc1cccc(Nc2ncc3C=C(C(=O)N(C)c3n2)c4c(Cl)cccc4Cl)c1\n", "Cc1nc(Nc2ncc(s2)C(=O)Nc3c(C)cccc3Cl)cc(n1)N4CCN(CCO)CC4\n", "COc1cc(Nc2c(cnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)C#N)c(Cl)cc1Cl\n", "CN1CCN(Cc2ccc(NC(=O)Nc3cc(C#Cc4cnc5cnccn45)n(C)n3)cc2C(F)(F)F)CC1\n", "CN1CCN(Cc2ccc(NC(=O)c3ccc(C)c(c3)C#Cc4cncc5nccn45)cc2C(F)(F)F)CC1\n", "CN1CCN(Cc2ccc(cc2)C(=O)Nc3ccc(C)c(Nc4nccc(n4)c5cccnc5)c3)CC1\n", "CCN1CCN(Cc2ccc(NC(=O)Nc3ccc(Oc4cc(NC)ncn4)cc3)cc2C(F)(F)F)CC1\n", "CN1CCN(Cc2ccc(NC(=O)Nc3cc(C#Cc4cnc5cccnn45)n(C)n3)cc2C(F)(F)F)CC1\n", "CN1CCN(Cc2ccc(cc2C(F)(F)F)C(=O)Nc3ccc(C)c(c3)C#Cc4cnc5cccnn45)CC1\n" ] } ], "source": [ "# next, we are retrieving details from the assay the activity was measured in\n", "# we keep binding and functional assays\n", "# compounds of 10nM or better are considered as actives\n", "# compounds of 10mycroM or worse are considered as inactives\n", "chembl.assay.set_format('xml')\n", "selected_actives = []\n", "selected_decoys = []\n", "for i in range(len(chembl_abl_activities)):\n", " x = chembl_abl_activities[i]\n", " ID = (x['assay_chembl_id'])\n", " details = chembl.assay.get(ID)\n", " d=xmltodict.parse(details)\n", " if(int(d['assay']['confidence_score']) == 9):\n", " if (d['assay']['assay_type'] in ['B','F']):\n", " if str(x['standard_units']) == 'nM':\n", " if float(x['standard_value']) < 10:\n", " selected_actives.append(x['canonical_smiles'])\n", " elif float(x['standard_value']) > 10000:\n", " selected_decoys.append(x['canonical_smiles'])\n", "#selected_actives = set(selected_actives) \n", "print (len(selected_actives), len(selected_decoys)) \n", "selected_actives = set(selected_actives)\n", "with open(\"ABL_smi\",\"w\") as fh:\n", " count = 0\n", " for e in selected_actives:\n", " print(e)\n", " count+=1\n", " fh.write(e + \"\\n\")" ] }, { "cell_type": "code", "execution_count": null, "metadata": { "collapsed": true }, "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": "3.6.0" } }, "nbformat": 4, "nbformat_minor": 2 }