{"id":"https://openalex.org/W4380577623","doi":"https://doi.org/10.1021/acs.jcim.3c00577","title":"Machine Learning Strategies for Reaction Development: Toward the Low-Data Limit","display_name":"Machine Learning Strategies for Reaction Development: Toward the Low-Data Limit","publication_year":2023,"publication_date":"2023-06-14","ids":{"openalex":"https://openalex.org/W4380577623","doi":"https://doi.org/10.1021/acs.jcim.3c00577","pmid":"https://pubmed.ncbi.nlm.nih.gov/37312524"},"language":"en","primary_location":{"id":"doi:10.1021/acs.jcim.3c00577","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.3c00577","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":"review","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/11163943","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5053256437","display_name":"Eunjae Shim","orcid":"https://orcid.org/0000-0002-4085-9659"},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Eunjae Shim","raw_affiliation_strings":["Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States"],"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5051918150","display_name":"Ambuj Tewari","orcid":"https://orcid.org/0000-0001-6969-7844"},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Ambuj Tewari","raw_affiliation_strings":["Department of Electrical Engineering and Computer Science, University of Michigan, Ann Arbor, Michigan 48109, United States","Department of Statistics, University of Michigan, Ann Arbor, Michigan 48109, United States"],"affiliations":[{"raw_affiliation_string":"Department of Electrical Engineering and Computer Science, University of Michigan, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]},{"raw_affiliation_string":"Department of Statistics, University of Michigan, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5056853464","display_name":"Tim Cernak","orcid":"https://orcid.org/0000-0001-5407-0643"},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Tim Cernak","raw_affiliation_strings":["Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States","Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States"],"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]},{"raw_affiliation_string":"Department of Medicinal Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5042777510","display_name":"Paul M. Zimmerman","orcid":"https://orcid.org/0000-0002-7444-1314"},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Paul M. Zimmerman","raw_affiliation_strings":["Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States"],"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States","institution_ids":["https://openalex.org/I27837315"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":4,"corresponding_author_ids":["https://openalex.org/A5042777510"],"corresponding_institution_ids":["https://openalex.org/I27837315"],"apc_list":null,"apc_paid":null,"fwci":3.4063,"has_fulltext":false,"cited_by_count":36,"citation_normalized_percentile":{"value":0.93679342,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":94,"max":100},"biblio":{"volume":"63","issue":"12","first_page":"3659","last_page":"3668"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11948","display_name":"Machine Learning in Materials Science","score":0.9995999932289124,"subfield":{"id":"https://openalex.org/subfields/2505","display_name":"Materials Chemistry"},"field":{"id":"https://openalex.org/fields/25","display_name":"Materials Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T11948","display_name":"Machine Learning in Materials Science","score":0.9995999932289124,"subfield":{"id":"https://openalex.org/subfields/2505","display_name":"Materials Chemistry"},"field":{"id":"https://openalex.org/fields/25","display_name":"Materials Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10211","display_name":"Computational Drug Discovery Methods","score":0.9871000051498413,"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/T12072","display_name":"Machine Learning and Algorithms","score":0.972599983215332,"subfield":{"id":"https://openalex.org/subfields/1702","display_name":"Artificial Intelligence"},"field":{"id":"https://openalex.org/fields/17","display_name":"Computer Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/transfer-of-learning","display_name":"Transfer of learning","score":0.6637672781944275},{"id":"https://openalex.org/keywords/computer-science","display_name":"Computer science","score":0.6288608908653259},{"id":"https://openalex.org/keywords/limit","display_name":"Limit (mathematics)","score":0.5941277146339417},{"id":"https://openalex.org/keywords/machine-learning","display_name":"Machine learning","score":0.5837644934654236},{"id":"https://openalex.org/keywords/perspective","display_name":"Perspective (graphical)","score":0.5714585781097412},{"id":"https://openalex.org/keywords/artificial-intelligence","display_name":"Artificial intelligence","score":0.5690908432006836},{"id":"https://openalex.org/keywords/active-learning","display_name":"Active learning (machine learning)","score":0.5016229152679443},{"id":"https://openalex.org/keywords/data-science","display_name":"Data science","score":0.41610297560691833},{"id":"https://openalex.org/keywords/mathematics","display_name":"Mathematics","score":0.08257228136062622}],"concepts":[{"id":"https://openalex.org/C150899416","wikidata":"https://www.wikidata.org/wiki/Q1820378","display_name":"Transfer of learning","level":2,"score":0.6637672781944275},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.6288608908653259},{"id":"https://openalex.org/C151201525","wikidata":"https://www.wikidata.org/wiki/Q177239","display_name":"Limit (mathematics)","level":2,"score":0.5941277146339417},{"id":"https://openalex.org/C119857082","wikidata":"https://www.wikidata.org/wiki/Q2539","display_name":"Machine learning","level":1,"score":0.5837644934654236},{"id":"https://openalex.org/C12713177","wikidata":"https://www.wikidata.org/wiki/Q1900281","display_name":"Perspective (graphical)","level":2,"score":0.5714585781097412},{"id":"https://openalex.org/C154945302","wikidata":"https://www.wikidata.org/wiki/Q11660","display_name":"Artificial intelligence","level":1,"score":0.5690908432006836},{"id":"https://openalex.org/C77967617","wikidata":"https://www.wikidata.org/wiki/Q4677561","display_name":"Active learning (machine learning)","level":2,"score":0.5016229152679443},{"id":"https://openalex.org/C2522767166","wikidata":"https://www.wikidata.org/wiki/Q2374463","display_name":"Data science","level":1,"score":0.41610297560691833},{"id":"https://openalex.org/C33923547","wikidata":"https://www.wikidata.org/wiki/Q395","display_name":"Mathematics","level":0,"score":0.08257228136062622},{"id":"https://openalex.org/C134306372","wikidata":"https://www.wikidata.org/wiki/Q7754","display_name":"Mathematical analysis","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D000069550","descriptor_name":"Machine Learning","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D011446","descriptor_name":"Prospective Studies","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011446","descriptor_name":"Prospective Studies","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011446","descriptor_name":"Prospective Studies","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011446","descriptor_name":"Prospective Studies","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011446","descriptor_name":"Prospective Studies","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":3,"locations":[{"id":"doi:10.1021/acs.jcim.3c00577","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.3c00577","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:37312524","is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/37312524","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},{"id":"pmh:oai:pubmedcentral.nih.gov:11163943","is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/11163943","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","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":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"J Chem Inf Model","raw_type":"Text"}],"best_oa_location":{"id":"pmh:oai:pubmedcentral.nih.gov:11163943","is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/11163943","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","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":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"J Chem Inf Model","raw_type":"Text"},"sustainable_development_goals":[],"awards":[{"id":"https://openalex.org/G206600186","display_name":null,"funder_award_id":"R35GM128830","funder_id":"https://openalex.org/F4320332161","funder_display_name":"National Institutes of Health"},{"id":"https://openalex.org/G22825293","display_name":null,"funder_award_id":"CHE-2236215","funder_id":"https://openalex.org/F4320306076","funder_display_name":"National Science Foundation"},{"id":"https://openalex.org/G7064466506","display_name":null,"funder_award_id":"IIS-2007055","funder_id":"https://openalex.org/F4320306076","funder_display_name":"National Science Foundation"}],"funders":[{"id":"https://openalex.org/F4320306076","display_name":"National Science Foundation","ror":"https://ror.org/021nxhr62"},{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":94,"referenced_works":["https://openalex.org/W29374554","https://openalex.org/W2006345381","https://openalex.org/W2017254234","https://openalex.org/W2021395631","https://openalex.org/W2067508454","https://openalex.org/W2096885367","https://openalex.org/W2135732933","https://openalex.org/W2165698076","https://openalex.org/W2192203593","https://openalex.org/W2293886700","https://openalex.org/W2347129741","https://openalex.org/W2412446857","https://openalex.org/W2478294658","https://openalex.org/W2511652057","https://openalex.org/W2512660405","https://openalex.org/W2747592475","https://openalex.org/W2769423117","https://openalex.org/W2784918212","https://openalex.org/W2785942661","https://openalex.org/W2794822175","https://openalex.org/W2799620402","https://openalex.org/W2799949122","https://openalex.org/W2802872171","https://openalex.org/W2804307771","https://openalex.org/W2830440988","https://openalex.org/W2899838818","https://openalex.org/W2903262661","https://openalex.org/W2908837618","https://openalex.org/W2910222073","https://openalex.org/W2947423323","https://openalex.org/W2959165901","https://openalex.org/W2965447776","https://openalex.org/W2971690404","https://openalex.org/W2972597827","https://openalex.org/W2976102057","https://openalex.org/W2981873522","https://openalex.org/W3002565078","https://openalex.org/W3008669240","https://openalex.org/W3012320417","https://openalex.org/W3012519883","https://openalex.org/W3015093215","https://openalex.org/W3017535706","https://openalex.org/W3021480024","https://openalex.org/W3023042104","https://openalex.org/W3033617175","https://openalex.org/W3042021489","https://openalex.org/W3042826782","https://openalex.org/W3067819707","https://openalex.org/W3085462416","https://openalex.org/W3088999551","https://openalex.org/W3098893481","https://openalex.org/W3100545487","https://openalex.org/W3103092523","https://openalex.org/W3103599793","https://openalex.org/W3118349318","https://openalex.org/W3121024033","https://openalex.org/W3128474010","https://openalex.org/W3156435654","https://openalex.org/W3156578609","https://openalex.org/W3160706794","https://openalex.org/W3161872738","https://openalex.org/W3164836307","https://openalex.org/W3176463279","https://openalex.org/W3181716552","https://openalex.org/W3205626500","https://openalex.org/W3207468551","https://openalex.org/W3209726219","https://openalex.org/W3211377821","https://openalex.org/W3212601637","https://openalex.org/W4205455490","https://openalex.org/W4224981068","https://openalex.org/W4225835448","https://openalex.org/W4225904177","https://openalex.org/W4226227198","https://openalex.org/W4248107770","https://openalex.org/W4283644061","https://openalex.org/W4288025837","https://openalex.org/W4290725232","https://openalex.org/W4295350584","https://openalex.org/W4306845856","https://openalex.org/W4307410169","https://openalex.org/W4310602585","https://openalex.org/W4311366447","https://openalex.org/W4311404181","https://openalex.org/W4312018894","https://openalex.org/W4312095228","https://openalex.org/W4315645746","https://openalex.org/W4317889697","https://openalex.org/W4318960502","https://openalex.org/W4320709089","https://openalex.org/W4321611726","https://openalex.org/W4327810158","https://openalex.org/W4360877714","https://openalex.org/W4362733319"],"related_works":["https://openalex.org/W1975467175","https://openalex.org/W2149537132","https://openalex.org/W1670566515","https://openalex.org/W641279757","https://openalex.org/W370975646","https://openalex.org/W596972243","https://openalex.org/W4242022592","https://openalex.org/W2018871932","https://openalex.org/W69751022","https://openalex.org/W4206195464"],"abstract_inverted_index":{"Machine":[0],"learning":[1,51,54,76,90],"models":[2],"are":[3,55],"increasingly":[4],"being":[5],"utilized":[6],"to":[7,22,31,94],"predict":[8],"outcomes":[9],"of":[10,17,47,74,106,109],"organic":[11,82],"chemical":[12,110],"reactions.":[13],"A":[14],"large":[15],"amount":[16],"reaction":[18],"data":[19],"is":[20,27],"used":[21],"train":[23],"these":[24,93],"models,":[25],"which":[26,64],"in":[28,61,81,103],"stark":[29],"contrast":[30],"how":[32],"expert":[33],"chemists":[34],"discover":[35],"and":[36,52,70,88,91,97],"develop":[37],"new":[38],"reactions":[39],"by":[40],"leveraging":[41],"information":[42],"from":[43],"a":[44],"small":[45],"number":[46],"relevant":[48],"transformations.":[49,111],"Transfer":[50],"active":[53,87],"two":[56],"strategies":[57],"that":[58],"can":[59],"operate":[60],"low-data":[62],"situations,":[63],"may":[65],"help":[66],"fill":[67],"this":[68],"gap":[69],"promote":[71],"the":[72,104],"use":[73],"machine":[75],"for":[77,99],"tackling":[78],"real-world":[79],"challenges":[80],"synthesis.":[83],"This":[84],"Perspective":[85],"introduces":[86],"transfer":[89],"connects":[92],"potential":[95],"opportunities":[96],"directions":[98],"further":[100],"research,":[101],"especially":[102],"area":[105],"prospective":[107],"development":[108]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":20},{"year":2024,"cited_by_count":12},{"year":2023,"cited_by_count":2}],"updated_date":"2026-04-11T08:14:18.477133","created_date":"2025-10-10T00:00:00"}