{"id":"https://openalex.org/W2016455326","doi":"https://doi.org/10.1007/s10822-010-9346-4","title":"Tautomerism in large databases","display_name":"Tautomerism in large databases","publication_year":2010,"publication_date":"2010-05-28","ids":{"openalex":"https://openalex.org/W2016455326","doi":"https://doi.org/10.1007/s10822-010-9346-4","mag":"2016455326","pmid":"https://pubmed.ncbi.nlm.nih.gov/20512400"},"language":"en","primary_location":{"id":"doi:10.1007/s10822-010-9346-4","is_oa":true,"landing_page_url":"https://doi.org/10.1007/s10822-010-9346-4","pdf_url":"https://link.springer.com/content/pdf/10.1007/s10822-010-9346-4.pdf","source":{"id":"https://openalex.org/S64621741","display_name":"Journal of Computer-Aided Molecular Design","issn_l":"0920-654X","issn":["0920-654X","1573-4951"],"is_oa":false,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310319900","host_organization_name":"Springer Science+Business Media","host_organization_lineage":["https://openalex.org/P4310319900","https://openalex.org/P4310319965"],"host_organization_lineage_names":["Springer Science+Business Media","Springer Nature"],"type":"journal"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Computer-Aided Molecular Design","raw_type":"journal-article"},"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"hybrid","oa_url":"https://link.springer.com/content/pdf/10.1007/s10822-010-9346-4.pdf","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5048549754","display_name":"Markus Sitzmann","orcid":null},"institutions":[],"countries":[],"is_corresponding":true,"raw_author_name":"Markus Sitzmann","raw_affiliation_strings":["Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, DHHS, NCI-Frederick, 376 Boyles St., Frederick, MD 21702, USA","Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, DHHS, NCI-Frederick, 376 Boyles St, Frederick, MD 21702, USA"],"affiliations":[{"raw_affiliation_string":"Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, DHHS, NCI-Frederick, 376 Boyles St., Frederick, MD 21702, USA","institution_ids":[]},{"raw_affiliation_string":"Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, DHHS, NCI-Frederick, 376 Boyles St, Frederick, MD 21702, USA","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110246499","display_name":"Wolf\u2010Dietrich Ihlenfeldt","orcid":null},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Wolf-Dietrich Ihlenfeldt","raw_affiliation_strings":["Xemistry GmbH, Hainholzweg 11, 61462, K\u00f6nigstein, Germany","Xemistry GmbH"],"affiliations":[{"raw_affiliation_string":"Xemistry GmbH, Hainholzweg 11, 61462, K\u00f6nigstein, Germany","institution_ids":[]},{"raw_affiliation_string":"Xemistry GmbH","institution_ids":[]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5078864876","display_name":"Marc C. Nicklaus","orcid":"https://orcid.org/0000-0002-4775-7030"},"institutions":[{"id":"https://openalex.org/I4210140884","display_name":"National Cancer Institute","ror":"https://ror.org/040gcmg81","country_code":"US","type":"government","lineage":["https://openalex.org/I1299022934","https://openalex.org/I1299303238","https://openalex.org/I4210140884"]},{"id":"https://openalex.org/I4210149717","display_name":"Center for Cancer Research","ror":"https://ror.org/05bjen692","country_code":"US","type":"facility","lineage":["https://openalex.org/I1299022934","https://openalex.org/I1299303238","https://openalex.org/I4210140884","https://openalex.org/I4210149717"]},{"id":"https://openalex.org/I1299303238","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88","country_code":"US","type":"government","lineage":["https://openalex.org/I1299022934","https://openalex.org/I1299303238"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Marc C. Nicklaus","raw_affiliation_strings":["Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, DHHS, NCI-Frederick, 376 Boyles St., Frederick, MD, 21702, USA","National Institutes of Health, DHHS, NCI-Frederick"],"affiliations":[{"raw_affiliation_string":"Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, DHHS, NCI-Frederick, 376 Boyles St., Frederick, MD, 21702, USA","institution_ids":["https://openalex.org/I1299303238","https://openalex.org/I4210140884","https://openalex.org/I4210149717"]},{"raw_affiliation_string":"National Institutes of Health, DHHS, NCI-Frederick","institution_ids":["https://openalex.org/I1299303238"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5048549754"],"corresponding_institution_ids":[],"apc_list":{"value":2890,"currency":"EUR","value_usd":3690},"apc_paid":{"value":2890,"currency":"EUR","value_usd":3690},"fwci":2.3926,"has_fulltext":true,"cited_by_count":83,"citation_normalized_percentile":{"value":0.8817089,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":90,"max":99},"biblio":{"volume":"24","issue":"6-7","first_page":"521","last_page":"551"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10211","display_name":"Computational Drug Discovery Methods","score":0.9998999834060669,"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":0.9998999834060669,"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/T10911","display_name":"Chemical Synthesis and Analysis","score":0.9965000152587891,"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/T10908","display_name":"Analytical Chemistry and Chromatography","score":0.9933000206947327,"subfield":{"id":"https://openalex.org/subfields/1607","display_name":"Spectroscopy"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/tautomer","display_name":"Tautomer","score":0.9734439849853516},{"id":"https://openalex.org/keywords/identifier","display_name":"Identifier","score":0.6179726719856262},{"id":"https://openalex.org/keywords/database","display_name":"Database","score":0.5776510238647461},{"id":"https://openalex.org/keywords/cheminformatics","display_name":"Cheminformatics","score":0.5754619836807251},{"id":"https://openalex.org/keywords/computer-science","display_name":"Computer science","score":0.5363579392433167},{"id":"https://openalex.org/keywords/set","display_name":"Set (abstract data type)","score":0.5123227834701538},{"id":"https://openalex.org/keywords/information-retrieval","display_name":"Information retrieval","score":0.3496648073196411},{"id":"https://openalex.org/keywords/chemistry","display_name":"Chemistry","score":0.3346342444419861},{"id":"https://openalex.org/keywords/computational-chemistry","display_name":"Computational chemistry","score":0.3267989158630371},{"id":"https://openalex.org/keywords/stereochemistry","display_name":"Stereochemistry","score":0.17748886346817017},{"id":"https://openalex.org/keywords/programming-language","display_name":"Programming language","score":0.09421461820602417}],"concepts":[{"id":"https://openalex.org/C111233374","wikidata":"https://www.wikidata.org/wiki/Q334640","display_name":"Tautomer","level":2,"score":0.9734439849853516},{"id":"https://openalex.org/C154504017","wikidata":"https://www.wikidata.org/wiki/Q853614","display_name":"Identifier","level":2,"score":0.6179726719856262},{"id":"https://openalex.org/C77088390","wikidata":"https://www.wikidata.org/wiki/Q8513","display_name":"Database","level":1,"score":0.5776510238647461},{"id":"https://openalex.org/C68762167","wikidata":"https://www.wikidata.org/wiki/Q910164","display_name":"Cheminformatics","level":2,"score":0.5754619836807251},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.5363579392433167},{"id":"https://openalex.org/C177264268","wikidata":"https://www.wikidata.org/wiki/Q1514741","display_name":"Set (abstract data type)","level":2,"score":0.5123227834701538},{"id":"https://openalex.org/C23123220","wikidata":"https://www.wikidata.org/wiki/Q816826","display_name":"Information retrieval","level":1,"score":0.3496648073196411},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.3346342444419861},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.3267989158630371},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.17748886346817017},{"id":"https://openalex.org/C199360897","wikidata":"https://www.wikidata.org/wiki/Q9143","display_name":"Programming language","level":1,"score":0.09421461820602417}],"mesh":[{"descriptor_ui":"D007536","descriptor_name":"Isomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007536","descriptor_name":"Isomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D007536","descriptor_name":"Isomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D016208","descriptor_name":"Databases, Factual","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D016208","descriptor_name":"Databases, Factual","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D016208","descriptor_name":"Databases, Factual","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D048088","descriptor_name":"Informatics","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D048088","descriptor_name":"Informatics","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D048088","descriptor_name":"Informatics","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":3,"locations":[{"id":"doi:10.1007/s10822-010-9346-4","is_oa":true,"landing_page_url":"https://doi.org/10.1007/s10822-010-9346-4","pdf_url":"https://link.springer.com/content/pdf/10.1007/s10822-010-9346-4.pdf","source":{"id":"https://openalex.org/S64621741","display_name":"Journal of Computer-Aided Molecular Design","issn_l":"0920-654X","issn":["0920-654X","1573-4951"],"is_oa":false,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310319900","host_organization_name":"Springer Science+Business Media","host_organization_lineage":["https://openalex.org/P4310319900","https://openalex.org/P4310319965"],"host_organization_lineage_names":["Springer Science+Business Media","Springer Nature"],"type":"journal"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Computer-Aided Molecular Design","raw_type":"journal-article"},{"id":"pmid:20512400","is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/20512400","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 computer-aided molecular design","raw_type":null},{"id":"pmh:oai:pubmedcentral.nih.gov:2886898","is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/2886898","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"J Comput Aided Mol Des","raw_type":"Text"}],"best_oa_location":{"id":"doi:10.1007/s10822-010-9346-4","is_oa":true,"landing_page_url":"https://doi.org/10.1007/s10822-010-9346-4","pdf_url":"https://link.springer.com/content/pdf/10.1007/s10822-010-9346-4.pdf","source":{"id":"https://openalex.org/S64621741","display_name":"Journal of Computer-Aided Molecular Design","issn_l":"0920-654X","issn":["0920-654X","1573-4951"],"is_oa":false,"is_in_doaj":false,"is_core":true,"host_organization":"https://openalex.org/P4310319900","host_organization_name":"Springer Science+Business Media","host_organization_lineage":["https://openalex.org/P4310319900","https://openalex.org/P4310319965"],"host_organization_lineage_names":["Springer Science+Business Media","Springer Nature"],"type":"journal"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of Computer-Aided Molecular Design","raw_type":"journal-article"},"sustainable_development_goals":[],"awards":[],"funders":[],"has_content":{"grobid_xml":true,"pdf":true},"content_urls":{"pdf":"https://content.openalex.org/works/W2016455326.pdf","grobid_xml":"https://content.openalex.org/works/W2016455326.grobid-xml"},"referenced_works_count":20,"referenced_works":["https://openalex.org/W1967829800","https://openalex.org/W2027423337","https://openalex.org/W2041587408","https://openalex.org/W2045873232","https://openalex.org/W2050083547","https://openalex.org/W2063140507","https://openalex.org/W2069878925","https://openalex.org/W2088221622","https://openalex.org/W2095663170","https://openalex.org/W2097186436","https://openalex.org/W2119284427","https://openalex.org/W2142602210","https://openalex.org/W2153693853","https://openalex.org/W2154033129","https://openalex.org/W2155741020","https://openalex.org/W2200017991","https://openalex.org/W2209568211","https://openalex.org/W2209889155","https://openalex.org/W2487649280","https://openalex.org/W2950696803"],"related_works":["https://openalex.org/W1994715304","https://openalex.org/W4297103231","https://openalex.org/W2006553579","https://openalex.org/W2070940942","https://openalex.org/W2106027604","https://openalex.org/W2361129091","https://openalex.org/W4323359560","https://openalex.org/W2884165437","https://openalex.org/W2082158222","https://openalex.org/W2744233384"],"abstract_inverted_index":{"We":[0],"have":[1],"used":[2],"the":[3,9,33,56,66,108,126,130,143,150,171,183,197,203,218,234,237],"Chemical":[4],"Structure":[5],"DataBase":[6],"(CSDB)":[7],"of":[8,16,32,38,90,111,125,134,170,180,182,196,205,217,233],"NCI":[10,57],"CADD":[11,58],"Group,":[12,59],"an":[13,177],"aggregated":[14],"collection":[15],"over":[17],"150":[18],"small-molecule":[19],"databases":[20,198,225],"totaling":[21],"103.5":[22],"million":[23,136],"structure":[24,52,145,185],"records,":[25,186],"to":[26,76,107,118],"conduct":[27],"tautomerism":[28,86],"analyses":[29],"on":[30,61],"one":[31,157],"largest":[34],"currently":[35],"existing":[36],"sets":[37],"real":[39],"(i.e.":[40,154],"not":[41],"computer-generated)":[42],"compounds.":[43],"This":[44],"analysis":[45],"was":[46,99,116,160,163,174,228],"carried":[47],"out":[48],"using":[49],"calculable":[50],"chemical":[51],"identifiers":[53],"developed":[54,73],"by":[55],"based":[60],"hash":[62],"codes":[63],"available":[64],"in":[65,95,129,199,214,226,236],"chemoinformatics":[67],"toolkit":[68],"CACTVS":[69],"and":[70,141],"a":[71,78,88,103,166],"newly":[72],"scoring":[74],"scheme":[75],"define":[77],"canonical":[79],"tautomer":[80],"for":[81,121,194,230],"any":[82],"encountered":[83],"structure.":[84],"CACTVS's":[85],"definition,":[87],"set":[89,204],"21":[91],"transform":[92],"rules":[93],"expressed":[94],"SMIRKS":[96],"line":[97],"notation,":[98],"used,":[100],"which":[101],"takes":[102],"comprehensive":[104],"stance":[105],"as":[106,189,191],"possible":[109,120],"types":[110],"tautomeric":[112,168],"interconversion":[113],"included.":[114],"Tautomerism":[115,147],"found":[117,175,229],"be":[119],"more":[122],"than":[123],"2/3":[124],"unique":[127,206],"structures":[128,207],"CSDB.":[131,200],"A":[132],"total":[133],"680":[135],"tautomers":[137],"were":[138],"calculated":[139],"from,":[140],"including,":[142],"original":[144,184],"records.":[146],"overlap":[148,221],"within":[149],"same":[151,172],"individual":[152],"database":[153],"at":[155,176],"least":[156],"other":[158],"entry":[159],"present":[161],"that":[162],"really":[164],"only":[165],"different":[167],"representation":[169],"compound)":[173],"average":[178],"rate":[179],"0.3%":[181],"with":[187],"values":[188],"high":[190],"nearly":[192,231],"2%":[193],"some":[195],"Projected":[201],"onto":[202],"(by":[208],"FICuS":[209],"identifier),":[210],"this":[211],"still":[212],"occurred":[213],"about":[215],"1.5%":[216],"cases.":[219],"Tautomeric":[220],"across":[222],"all":[223],"constituent":[224],"CSDB":[227],"10%":[232],"records":[235],"collection.":[238]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":4},{"year":2024,"cited_by_count":6},{"year":2023,"cited_by_count":5},{"year":2022,"cited_by_count":9},{"year":2021,"cited_by_count":10},{"year":2020,"cited_by_count":9},{"year":2019,"cited_by_count":2},{"year":2018,"cited_by_count":8},{"year":2017,"cited_by_count":4},{"year":2016,"cited_by_count":4},{"year":2015,"cited_by_count":6},{"year":2014,"cited_by_count":5},{"year":2013,"cited_by_count":2},{"year":2012,"cited_by_count":1}],"updated_date":"2026-04-21T08:09:41.155169","created_date":"2025-10-10T00:00:00"}