{"id":"https://openalex.org/W3034910277","doi":"https://doi.org/10.1021/acs.jcim.0c00293","title":"Prediction of Natural Product Classes Using Machine Learning and <sup>13</sup>C NMR Spectroscopic Data","display_name":"Prediction of Natural Product Classes Using Machine Learning and <sup>13</sup>C NMR Spectroscopic Data","publication_year":2020,"publication_date":"2020-06-15","ids":{"openalex":"https://openalex.org/W3034910277","doi":"https://doi.org/10.1021/acs.jcim.0c00293","mag":"3034910277","pmid":"https://pubmed.ncbi.nlm.nih.gov/32538625"},"language":"en","primary_location":{"id":"doi:10.1021/acs.jcim.0c00293","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.0c00293","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/A5050771815","display_name":"Sa\u00fal H. Mart\u00ednez-Trevi\u00f1o","orcid":"https://orcid.org/0000-0001-7240-8863"},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Sa\u00fal H. Mart\u00ednez-Trevi\u00f1o","raw_affiliation_strings":["Departamento de F\u0131\u0301sica Aplicada, Centro de Investigaci\u00f3n y de Estudios Avanzados, Km. 6 Antigua carretera a Progreso Apdo. Postal 73, Cordemex, 97310 M\u00e9rida, Mexico"],"raw_orcid":"https://orcid.org/0000-0001-7240-8863","affiliations":[{"raw_affiliation_string":"Departamento de F\u0131\u0301sica Aplicada, Centro de Investigaci\u00f3n y de Estudios Avanzados, Km. 6 Antigua carretera a Progreso Apdo. Postal 73, Cordemex, 97310 M\u00e9rida, Mexico","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5007082510","display_name":"V\u00edctor Uc-Cetina","orcid":"https://orcid.org/0000-0002-4713-3762"},"institutions":[{"id":"https://openalex.org/I23878562","display_name":"Autonomous University of Yucat\u00e1n","ror":"https://ror.org/032p1n739","country_code":"MX","type":"education","lineage":["https://openalex.org/I23878562"]}],"countries":["MX"],"is_corresponding":false,"raw_author_name":"V\u00edctor Uc-Cetina","raw_affiliation_strings":["Facultad de Matem\u00e1ticas, Universidad Aut\u00f3noma de Yucat\u00e1n, Av. Industrias no contaminantes, S/N, 97119 M\u00e9rida, Yucat\u00e1n, Mexico"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Facultad de Matem\u00e1ticas, Universidad Aut\u00f3noma de Yucat\u00e1n, Av. Industrias no contaminantes, S/N, 97119 M\u00e9rida, Yucat\u00e1n, Mexico","institution_ids":["https://openalex.org/I23878562"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5014465025","display_name":"Mar\u00eda A. Fern\u00e1ndez\u2010Herrera","orcid":null},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Mar\u00eda A. Fern\u00e1ndez-Herrera","raw_affiliation_strings":["Departamento de F\u0131\u0301sica Aplicada, Centro de Investigaci\u00f3n y de Estudios Avanzados, Km. 6 Antigua carretera a Progreso Apdo. Postal 73, Cordemex, 97310 M\u00e9rida, Mexico"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departamento de F\u0131\u0301sica Aplicada, Centro de Investigaci\u00f3n y de Estudios Avanzados, Km. 6 Antigua carretera a Progreso Apdo. Postal 73, Cordemex, 97310 M\u00e9rida, Mexico","institution_ids":[]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5035678236","display_name":"Gabriel Merino","orcid":"https://orcid.org/0000-0003-1961-8321"},"institutions":[],"countries":[],"is_corresponding":true,"raw_author_name":"Gabriel Merino","raw_affiliation_strings":["Departamento de F\u0131\u0301sica Aplicada, Centro de Investigaci\u00f3n y de Estudios Avanzados, Km. 6 Antigua carretera a Progreso Apdo. Postal 73, Cordemex, 97310 M\u00e9rida, Mexico"],"raw_orcid":"https://orcid.org/0000-0003-1961-8321","affiliations":[{"raw_affiliation_string":"Departamento de F\u0131\u0301sica Aplicada, Centro de Investigaci\u00f3n y de Estudios Avanzados, Km. 6 Antigua carretera a Progreso Apdo. Postal 73, Cordemex, 97310 M\u00e9rida, Mexico","institution_ids":[]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":4,"corresponding_author_ids":["https://openalex.org/A5035678236"],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":3.0023,"has_fulltext":false,"cited_by_count":50,"citation_normalized_percentile":{"value":0.92304339,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":98,"max":99},"biblio":{"volume":"60","issue":"7","first_page":"3376","last_page":"3386"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10836","display_name":"Metabolomics and Mass Spectrometry Studies","score":0.9984999895095825,"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"}},"topics":[{"id":"https://openalex.org/T10836","display_name":"Metabolomics and Mass Spectrometry Studies","score":0.9984999895095825,"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/T10211","display_name":"Computational Drug Discovery Methods","score":0.9983999729156494,"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/T10908","display_name":"Analytical Chemistry and Chromatography","score":0.9944000244140625,"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/natural-product","display_name":"Natural product","score":0.5351496934890747},{"id":"https://openalex.org/keywords/classifier","display_name":"Classifier (UML)","score":0.5141828060150146},{"id":"https://openalex.org/keywords/carbon-13-nmr","display_name":"Carbon-13 NMR","score":0.5017902851104736},{"id":"https://openalex.org/keywords/artificial-intelligence","display_name":"Artificial intelligence","score":0.4529586434364319},{"id":"https://openalex.org/keywords/data-set","display_name":"Data set","score":0.44745156168937683},{"id":"https://openalex.org/keywords/computer-science","display_name":"Computer science","score":0.41707348823547363},{"id":"https://openalex.org/keywords/chemistry","display_name":"Chemistry","score":0.3795376121997833},{"id":"https://openalex.org/keywords/machine-learning","display_name":"Machine learning","score":0.351590633392334},{"id":"https://openalex.org/keywords/stereochemistry","display_name":"Stereochemistry","score":0.14897745847702026}],"concepts":[{"id":"https://openalex.org/C2779396153","wikidata":"https://www.wikidata.org/wiki/Q901227","display_name":"Natural product","level":2,"score":0.5351496934890747},{"id":"https://openalex.org/C95623464","wikidata":"https://www.wikidata.org/wiki/Q1096149","display_name":"Classifier (UML)","level":2,"score":0.5141828060150146},{"id":"https://openalex.org/C163111631","wikidata":"https://www.wikidata.org/wiki/Q1952454","display_name":"Carbon-13 NMR","level":2,"score":0.5017902851104736},{"id":"https://openalex.org/C154945302","wikidata":"https://www.wikidata.org/wiki/Q11660","display_name":"Artificial intelligence","level":1,"score":0.4529586434364319},{"id":"https://openalex.org/C58489278","wikidata":"https://www.wikidata.org/wiki/Q1172284","display_name":"Data set","level":2,"score":0.44745156168937683},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.41707348823547363},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.3795376121997833},{"id":"https://openalex.org/C119857082","wikidata":"https://www.wikidata.org/wiki/Q2539","display_name":"Machine learning","level":1,"score":0.351590633392334},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.14897745847702026}],"mesh":[{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D001688","descriptor_name":"Biological Products","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D001688","descriptor_name":"Biological Products","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D001688","descriptor_name":"Biological Products","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D008279","descriptor_name":"Magnetic Resonance Imaging","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008279","descriptor_name":"Magnetic Resonance Imaging","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008279","descriptor_name":"Magnetic Resonance Imaging","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","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":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","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":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/acs.jcim.0c00293","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.0c00293","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:32538625","is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/32538625","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":[{"display_name":"Responsible consumption and production","id":"https://metadata.un.org/sdg/12","score":0.4399999976158142}],"awards":[{"id":"https://openalex.org/G2343989487","display_name":null,"funder_award_id":"CB-2015-252356","funder_id":"https://openalex.org/F4320321739","funder_display_name":"Consejo Nacional de Ciencia y Tecnolog\u00eda"},{"id":"https://openalex.org/G6713543907","display_name":null,"funder_award_id":"CB-2015-254742","funder_id":"https://openalex.org/F4320321739","funder_display_name":"Consejo Nacional de Ciencia y Tecnolog\u00eda"}],"funders":[{"id":"https://openalex.org/F4320321739","display_name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","ror":"https://ror.org/059ex5q34"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":85,"referenced_works":["https://openalex.org/W197484301","https://openalex.org/W1554944419","https://openalex.org/W1579551049","https://openalex.org/W1583837637","https://openalex.org/W1963550113","https://openalex.org/W1968166882","https://openalex.org/W1976923275","https://openalex.org/W1984967337","https://openalex.org/W1997172971","https://openalex.org/W1999145583","https://openalex.org/W2022477494","https://openalex.org/W2035605813","https://openalex.org/W2046490939","https://openalex.org/W2068223321","https://openalex.org/W2076009699","https://openalex.org/W2094598047","https://openalex.org/W2094914511","https://openalex.org/W2100234166","https://openalex.org/W2101234009","https://openalex.org/W2104933073","https://openalex.org/W2113569080","https://openalex.org/W2115974175","https://openalex.org/W2117391900","https://openalex.org/W2159645460","https://openalex.org/W2161671078","https://openalex.org/W2170505850","https://openalex.org/W2256742438","https://openalex.org/W2295598076","https://openalex.org/W2396003913","https://openalex.org/W2522142774","https://openalex.org/W2600989413","https://openalex.org/W2743335233","https://openalex.org/W2766447205","https://openalex.org/W2768841990","https://openalex.org/W2788797421","https://openalex.org/W2789297614","https://openalex.org/W2789469875","https://openalex.org/W2791336180","https://openalex.org/W2791957075","https://openalex.org/W2793539103","https://openalex.org/W2794818609","https://openalex.org/W2794969704","https://openalex.org/W2796170095","https://openalex.org/W2800101543","https://openalex.org/W2801179325","https://openalex.org/W2804256532","https://openalex.org/W2806405494","https://openalex.org/W2808074947","https://openalex.org/W2808127013","https://openalex.org/W2808591442","https://openalex.org/W2808626195","https://openalex.org/W2883583109","https://openalex.org/W2887795636","https://openalex.org/W2888937068","https://openalex.org/W2900694120","https://openalex.org/W2900944465","https://openalex.org/W2904551315","https://openalex.org/W2906047849","https://openalex.org/W2906984698","https://openalex.org/W2907481468","https://openalex.org/W2908285585","https://openalex.org/W2911195053","https://openalex.org/W2917058797","https://openalex.org/W2919115771","https://openalex.org/W2919197060","https://openalex.org/W2924650933","https://openalex.org/W2924802680","https://openalex.org/W2930712613","https://openalex.org/W2939421894","https://openalex.org/W2940892137","https://openalex.org/W2943346828","https://openalex.org/W2944479606","https://openalex.org/W2945656536","https://openalex.org/W2946018214","https://openalex.org/W2946995677","https://openalex.org/W2947540288","https://openalex.org/W2950405675","https://openalex.org/W2950810008","https://openalex.org/W2953128081","https://openalex.org/W2953273646","https://openalex.org/W2971876021","https://openalex.org/W3155649056","https://openalex.org/W4210987854","https://openalex.org/W4233450452","https://openalex.org/W4294120837"],"related_works":["https://openalex.org/W2968368302","https://openalex.org/W2414309485","https://openalex.org/W1851279709","https://openalex.org/W2731175684","https://openalex.org/W3148197098","https://openalex.org/W4367595722","https://openalex.org/W2107628403","https://openalex.org/W3137353528","https://openalex.org/W1993117992","https://openalex.org/W2160898397"],"abstract_inverted_index":{"Structure":[0],"elucidation":[1],"of":[2,22,30,37,41,61,68,82,91,107,117],"chemical":[3],"compounds":[4],"is":[5,28],"a":[6,23],"complex":[7],"and":[8,14,152],"challenging":[9],"activity":[10],"that":[11,47],"requires":[12],"expertise":[13],"well-suited":[15],"tools.":[16],"To":[17],"assign":[18],"the":[19,31,66,89,102,121,129,140,145,149,153],"molecular":[20],"structure":[21],"given":[24],"compound,":[25],"13C":[26,73,79],"NMR":[27,74,80],"one":[29],"most":[32,137],"widely":[33],"used":[34],"techniques":[35],"because":[36,60],"its":[38],"broad":[39],"range":[40],"structural":[42,62],"information.":[43],"Taking":[44],"into":[45,55],"account":[46],"molecules":[48],"found":[49],"in":[50],"nature":[51],"can":[52],"be":[53],"grouped":[54],"natural":[56],"product":[57],"(NP)":[58],"classes":[59],"similarities,":[63],"we":[64,84,125,143],"explore":[65],"possibility":[67],"NP":[69,94],"class":[70],"prediction":[71,90,154],"via":[72],"data.":[75],"Employing":[76],"freely":[77],"available":[78],"data":[81,130],"NPs,":[83],"trained":[85],"four":[86],"classifiers":[87],"for":[88,136],"eight":[92],"common":[93],"classes.":[95,138],"The":[96],"best":[97],"performance":[98],"was":[99],"obtained":[100],"with":[101,114],"XGBoost":[103],"classifier":[104],"reaching":[105],"f1-scores":[106],"above":[108,134],"0.82.":[109],"We":[110],"also":[111],"performed":[112],"experiments":[113],"different":[115],"percentages":[116],"positive":[118],"samples,":[119],"including":[120],"glycoside":[122],"presence.":[123],"Furthermore,":[124],"tested":[126],"cases":[127],"outside":[128],"set,":[131],"yielding":[132],"performances":[133],"80%":[135],"For":[139],"chromans":[141],"case,":[142],"restricted":[144],"test":[146],"examples":[147],"to":[148,157],"coumarin":[150],"subclass,":[151],"accuracy":[155],"increased":[156],"100%.":[158]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":7},{"year":2024,"cited_by_count":5},{"year":2023,"cited_by_count":14},{"year":2022,"cited_by_count":6},{"year":2021,"cited_by_count":10},{"year":2020,"cited_by_count":6}],"updated_date":"2026-05-16T08:24:45.110214","created_date":"2025-10-10T00:00:00"}