{"id":"https://openalex.org/W1964245184","doi":"https://doi.org/10.1021/ci9004354","title":"Predicting Oral Druglikeness by Iterative Stochastic Elimination","display_name":"Predicting Oral Druglikeness by Iterative Stochastic Elimination","publication_year":2010,"publication_date":"2010-02-19","ids":{"openalex":"https://openalex.org/W1964245184","doi":"https://doi.org/10.1021/ci9004354","mag":"1964245184","pmid":"https://pubmed.ncbi.nlm.nih.gov/20170135"},"language":"en","primary_location":{"id":"doi:10.1021/ci9004354","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ci9004354","pdf_url":null,"source":{"id":"https://openalex.org/S167262187","display_name":"Journal of Chemical Information and Modeling","issn_l":"1549-9596","issn":["1549-9596","1549-960X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Chemical Information and Modeling","raw_type":"journal-article"},"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5071300811","display_name":"Anwar Rayan","orcid":"https://orcid.org/0000-0001-8255-5947"},"institutions":[{"id":"https://openalex.org/I197251160","display_name":"Hebrew University of Jerusalem","ror":"https://ror.org/03qxff017","country_code":"IL","type":"education","lineage":["https://openalex.org/I197251160"]}],"countries":["IL"],"is_corresponding":true,"raw_author_name":"Anwar Rayan","raw_affiliation_strings":["Molecular Modeling and Drug Design Lab and the Alex Grass Center for Drug Design and Synthesis, Institute of Drug Research, The Hebrew University of Jerusalem 91120 Israel"],"affiliations":[{"raw_affiliation_string":"Molecular Modeling and Drug Design Lab and the Alex Grass Center for Drug Design and Synthesis, Institute of Drug Research, The Hebrew University of Jerusalem 91120 Israel","institution_ids":["https://openalex.org/I197251160"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5084806194","display_name":"David Marcus","orcid":"https://orcid.org/0000-0001-8932-4906"},"institutions":[{"id":"https://openalex.org/I197251160","display_name":"Hebrew University of Jerusalem","ror":"https://ror.org/03qxff017","country_code":"IL","type":"education","lineage":["https://openalex.org/I197251160"]}],"countries":["IL"],"is_corresponding":false,"raw_author_name":"David Marcus","raw_affiliation_strings":["Molecular Modeling and Drug Design Lab and the Alex Grass Center for Drug Design and Synthesis, Institute of Drug Research, The Hebrew University of Jerusalem 91120 Israel"],"affiliations":[{"raw_affiliation_string":"Molecular Modeling and Drug Design Lab and the Alex Grass Center for Drug Design and Synthesis, Institute of Drug Research, The Hebrew University of Jerusalem 91120 Israel","institution_ids":["https://openalex.org/I197251160"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5045868274","display_name":"Amiram Goldblum","orcid":"https://orcid.org/0000-0002-9344-3673"},"institutions":[{"id":"https://openalex.org/I197251160","display_name":"Hebrew University of Jerusalem","ror":"https://ror.org/03qxff017","country_code":"IL","type":"education","lineage":["https://openalex.org/I197251160"]}],"countries":["IL"],"is_corresponding":false,"raw_author_name":"Amiram Goldblum","raw_affiliation_strings":["Molecular Modeling and Drug Design Lab and the Alex Grass Center for Drug Design and Synthesis, Institute of Drug Research, The Hebrew University of Jerusalem 91120 Israel"],"affiliations":[{"raw_affiliation_string":"Molecular Modeling and Drug Design Lab and the Alex Grass Center for Drug Design and Synthesis, Institute of Drug Research, The Hebrew University of Jerusalem 91120 Israel","institution_ids":["https://openalex.org/I197251160"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5071300811"],"corresponding_institution_ids":["https://openalex.org/I197251160"],"apc_list":null,"apc_paid":null,"fwci":2.77658481,"has_fulltext":false,"cited_by_count":28,"citation_normalized_percentile":{"value":0.89130773,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":97},"biblio":{"volume":"50","issue":"3","first_page":"437","last_page":"445"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10211","display_name":"Computational Drug Discovery Methods","score":1.0,"subfield":{"id":"https://openalex.org/subfields/1703","display_name":"Computational Theory and Mathematics"},"field":{"id":"https://openalex.org/fields/17","display_name":"Computer Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T10211","display_name":"Computational Drug Discovery Methods","score":1.0,"subfield":{"id":"https://openalex.org/subfields/1703","display_name":"Computational Theory and Mathematics"},"field":{"id":"https://openalex.org/fields/17","display_name":"Computer Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10836","display_name":"Metabolomics and Mass Spectrometry Studies","score":0.9794999957084656,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T12878","display_name":"Pharmaceutical Quality and Counterfeiting","score":0.977400004863739,"subfield":{"id":"https://openalex.org/subfields/2739","display_name":"Public Health, Environmental and Occupational Health"},"field":{"id":"https://openalex.org/fields/27","display_name":"Medicine"},"domain":{"id":"https://openalex.org/domains/4","display_name":"Health Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/computer-science","display_name":"Computer science","score":0.6365891695022583},{"id":"https://openalex.org/keywords/discriminative-model","display_name":"Discriminative model","score":0.6151286959648132},{"id":"https://openalex.org/keywords/ranking","display_name":"Ranking (information retrieval)","score":0.49297547340393066},{"id":"https://openalex.org/keywords/set","display_name":"Set (abstract data type)","score":0.4850122630596161},{"id":"https://openalex.org/keywords/drug-discovery","display_name":"Drug discovery","score":0.4256626069545746},{"id":"https://openalex.org/keywords/filter","display_name":"Filter (signal processing)","score":0.42342475056648254},{"id":"https://openalex.org/keywords/data-mining","display_name":"Data mining","score":0.4156950116157532},{"id":"https://openalex.org/keywords/artificial-intelligence","display_name":"Artificial intelligence","score":0.38290441036224365},{"id":"https://openalex.org/keywords/machine-learning","display_name":"Machine learning","score":0.3818451762199402},{"id":"https://openalex.org/keywords/chemistry","display_name":"Chemistry","score":0.11948475241661072}],"concepts":[{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.6365891695022583},{"id":"https://openalex.org/C97931131","wikidata":"https://www.wikidata.org/wiki/Q5282087","display_name":"Discriminative model","level":2,"score":0.6151286959648132},{"id":"https://openalex.org/C189430467","wikidata":"https://www.wikidata.org/wiki/Q7293293","display_name":"Ranking (information retrieval)","level":2,"score":0.49297547340393066},{"id":"https://openalex.org/C177264268","wikidata":"https://www.wikidata.org/wiki/Q1514741","display_name":"Set (abstract data type)","level":2,"score":0.4850122630596161},{"id":"https://openalex.org/C74187038","wikidata":"https://www.wikidata.org/wiki/Q1418791","display_name":"Drug discovery","level":2,"score":0.4256626069545746},{"id":"https://openalex.org/C106131492","wikidata":"https://www.wikidata.org/wiki/Q3072260","display_name":"Filter (signal processing)","level":2,"score":0.42342475056648254},{"id":"https://openalex.org/C124101348","wikidata":"https://www.wikidata.org/wiki/Q172491","display_name":"Data mining","level":1,"score":0.4156950116157532},{"id":"https://openalex.org/C154945302","wikidata":"https://www.wikidata.org/wiki/Q11660","display_name":"Artificial intelligence","level":1,"score":0.38290441036224365},{"id":"https://openalex.org/C119857082","wikidata":"https://www.wikidata.org/wiki/Q2539","display_name":"Machine learning","level":1,"score":0.3818451762199402},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.11948475241661072},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.0},{"id":"https://openalex.org/C199360897","wikidata":"https://www.wikidata.org/wiki/Q9143","display_name":"Programming language","level":1,"score":0.0},{"id":"https://openalex.org/C31972630","wikidata":"https://www.wikidata.org/wiki/Q844240","display_name":"Computer vision","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D000465","descriptor_name":"Algorithms","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D001682","descriptor_name":"Biological Availability","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D016208","descriptor_name":"Databases, Factual","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D055808","descriptor_name":"Drug Discovery","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009055","descriptor_name":"Mouth","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004364","descriptor_name":"Pharmaceutical Preparations","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013269","descriptor_name":"Stochastic Processes","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000465","descriptor_name":"Algorithms","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D001682","descriptor_name":"Biological Availability","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D016208","descriptor_name":"Databases, Factual","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D055808","descriptor_name":"Drug Discovery","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009055","descriptor_name":"Mouth","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004364","descriptor_name":"Pharmaceutical Preparations","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013269","descriptor_name":"Stochastic Processes","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000465","descriptor_name":"Algorithms","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D001682","descriptor_name":"Biological Availability","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D016208","descriptor_name":"Databases, Factual","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D055808","descriptor_name":"Drug Discovery","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009055","descriptor_name":"Mouth","qualifier_ui":"Q000378","qualifier_name":"metabolism","is_major_topic":false},{"descriptor_ui":"D004364","descriptor_name":"Pharmaceutical Preparations","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D013269","descriptor_name":"Stochastic Processes","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/ci9004354","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ci9004354","pdf_url":null,"source":{"id":"https://openalex.org/S167262187","display_name":"Journal of Chemical Information and Modeling","issn_l":"1549-9596","issn":["1549-9596","1549-960X"],"is_oa":false,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Chemical Information and Modeling","raw_type":"journal-article"},{"id":"pmid:20170135","is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/20170135","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of chemical information and modeling","raw_type":null}],"best_oa_location":null,"sustainable_development_goals":[{"id":"https://metadata.un.org/sdg/10","display_name":"Reduced inequalities","score":0.5799999833106995}],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":71,"referenced_works":["https://openalex.org/W82186612","https://openalex.org/W1487233798","https://openalex.org/W1574994167","https://openalex.org/W1969231756","https://openalex.org/W1974751086","https://openalex.org/W1975293246","https://openalex.org/W1978009405","https://openalex.org/W1989451208","https://openalex.org/W1990195871","https://openalex.org/W1990878163","https://openalex.org/W1993605104","https://openalex.org/W2000005919","https://openalex.org/W2003076573","https://openalex.org/W2003873735","https://openalex.org/W2005263430","https://openalex.org/W2007365648","https://openalex.org/W2007697155","https://openalex.org/W2009052065","https://openalex.org/W2010304681","https://openalex.org/W2010595835","https://openalex.org/W2011505858","https://openalex.org/W2012704983","https://openalex.org/W2020116600","https://openalex.org/W2020567606","https://openalex.org/W2021592048","https://openalex.org/W2024674972","https://openalex.org/W2032353075","https://openalex.org/W2033062180","https://openalex.org/W2035419902","https://openalex.org/W2039478311","https://openalex.org/W2039773298","https://openalex.org/W2042107474","https://openalex.org/W2043293105","https://openalex.org/W2046564413","https://openalex.org/W2047710091","https://openalex.org/W2055142184","https://openalex.org/W2058253769","https://openalex.org/W2060581674","https://openalex.org/W2062458432","https://openalex.org/W2064885619","https://openalex.org/W2068950612","https://openalex.org/W2069506489","https://openalex.org/W2073887042","https://openalex.org/W2074596609","https://openalex.org/W2080242559","https://openalex.org/W2080245527","https://openalex.org/W2085789404","https://openalex.org/W2088449942","https://openalex.org/W2101257231","https://openalex.org/W2105649494","https://openalex.org/W2111771265","https://openalex.org/W2112664428","https://openalex.org/W2130403843","https://openalex.org/W2142328147","https://openalex.org/W2145781320","https://openalex.org/W2149658535","https://openalex.org/W2151356831","https://openalex.org/W2152681556","https://openalex.org/W2154033129","https://openalex.org/W2159469951","https://openalex.org/W2166096070","https://openalex.org/W2166465687","https://openalex.org/W2214291252","https://openalex.org/W2214798411","https://openalex.org/W2318578326","https://openalex.org/W2324996872","https://openalex.org/W2327839171","https://openalex.org/W2950780616","https://openalex.org/W3175318380","https://openalex.org/W4235312057","https://openalex.org/W4248107770"],"related_works":["https://openalex.org/W2899084033","https://openalex.org/W2983744209","https://openalex.org/W2961085424","https://openalex.org/W2026121273","https://openalex.org/W2801772698","https://openalex.org/W66955737","https://openalex.org/W2102106825","https://openalex.org/W4306674287","https://openalex.org/W2752271443","https://openalex.org/W2073139667"],"abstract_inverted_index":{"Integration":[0],"of":[1,8,14,53,73,92,97,101,124,160,168,216,237,242,248,271],"computational":[2],"methods":[3,252],"in":[4,18,84,145,151,193,199,262],"the":[5,15,19,56,98,119,129,214,224,238,249,263,269],"early":[6],"stages":[7],"drug":[9,26,201,229],"discovery":[10],"has":[11,181,259],"been":[12],"one":[13,166,189],"key":[16],"trends":[17],"pharmaceutical":[20],"industry.":[21],"Starting":[22],"with":[23,158,223],"high":[24,164],"quality":[25],"candidates":[27,202],"should":[28],"ultimately":[29],"minimize":[30],"clinical":[31],"attrition":[32],"rates":[33],"and":[34,68,103,147,175,274,277],"give":[35],"rise":[36],"to":[37,88,105,142,204,207,219,235,246],"higher":[38],"success":[39,270],"rates.":[40],"In":[41],"this":[42,85,243],"paper,":[43],"we":[44,62,117],"present":[45],"a":[46,80,107],"novel":[47],"approach":[48,218,258],"for":[49,253],"indexing":[50],"oral":[51,210],"druglikeness":[52],"compounds.":[54],"With":[55],"Iterative":[57],"Stochastic":[58],"Elimination":[59],"(ISE)":[60],"Algorithm,":[61],"distinguish":[63],"between":[64],"orally":[65,227],"available":[66],"drugs":[67],"nondrugs":[69],"by":[70,114,127],"generating":[71],"sets":[72,95,159],"optimized":[74],"descriptors'":[75],"ranges,":[76],"each":[77],"set":[78],"constituting":[79],"\"filter\".":[81],"We":[82,212],"delineate":[83],"paper":[86],"how":[87,104],"produce":[89],"an":[90,132],"ensemble":[91],"best":[93],"k-descriptor":[94],"out":[96],"huge":[99],"number":[100],"possibilities,":[102],"construct":[106],"\"filter":[108],"bank\"":[109],"that":[110,231,256],"retains":[111],"diverse":[112],"filters":[113,130],"clustering.":[115],"Finally,":[116],"define":[118],"\"orally":[120],"bioavailable":[121,228],"drug-like\"":[122],"character":[123],"individual":[125],"molecules":[126,144],"combining":[128],"into":[131],"\"Orally":[133],"Bioavailable":[134],"Druglike":[135],"Index\"":[136],"(OB-DLI)":[137],"which":[138,267],"may":[139],"be":[140,208],"used":[141],"prioritize":[143],"databases":[146],"discuss":[148],"its":[149],"uses":[150],"several":[152],"potential":[153],"applications.":[154],"The":[155],"predictive":[156],"power":[157,196],"4-6":[161],"descriptors":[162,170],"is":[163],"(i.e.,":[165],"filter":[167],"5":[169],"retrieved":[171],"81%":[172],"true":[173,177,273],"positives":[174,276],">77%":[176],"negatives).":[178],"Thus,":[179],"OB-DLI":[180],"advantages":[182],"over":[183],"binary":[184],"decisions":[185],"(that":[186],"use":[187],"only":[188,192],"filter)":[190],"not":[191],"raising":[194],"discriminative":[195],"but":[197],"also":[198],"ranking":[200],"according":[203],"their":[205],"chance":[206],"successful":[209],"drugs.":[211],"demonstrate":[213],"ability":[215],"our":[217,257],"discover":[220],"molecular":[221],"entities":[222],"required":[225],"property,":[226],"likeness,":[230],"are":[232],"structurally":[233],"dissimilar":[234],"those":[236],"training":[239],"set.":[240],"Comparison":[241],"ISE":[244],"application":[245],"some":[247],"current":[250],"main":[251],"classification":[254],"reveals":[255],">13%":[260],"improvement":[261],"Matthews":[264],"Correlation":[265],"Coefficient,":[266],"measures":[268],"identifying":[272],"false":[275],"negatives.":[278]},"counts_by_year":[{"year":2024,"cited_by_count":2},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":3},{"year":2019,"cited_by_count":3},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":3},{"year":2016,"cited_by_count":2},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":1},{"year":2012,"cited_by_count":3}],"updated_date":"2025-11-06T03:46:38.306776","created_date":"2025-10-10T00:00:00"}