{"id":"https://openalex.org/W2906079471","doi":"https://doi.org/10.1021/acs.jcim.8b00622","title":"Predicting the Magnitude of \u03c3-Holes Using VmaxPred, a Fast and Efficient Tool Supporting the Application of Halogen Bonds in Drug Discovery","display_name":"Predicting the Magnitude of \u03c3-Holes Using VmaxPred, a Fast and Efficient Tool Supporting the Application of Halogen Bonds in Drug Discovery","publication_year":2018,"publication_date":"2018-12-24","ids":{"openalex":"https://openalex.org/W2906079471","doi":"https://doi.org/10.1021/acs.jcim.8b00622","mag":"2906079471","pmid":"https://pubmed.ncbi.nlm.nih.gov/30582814"},"language":"en","primary_location":{"id":"doi:10.1021/acs.jcim.8b00622","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.8b00622","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/A5002907072","display_name":"Johannes Heidrich","orcid":"https://orcid.org/0000-0002-6637-6989"},"institutions":[{"id":"https://openalex.org/I8087733","display_name":"University of T\u00fcbingen","ror":"https://ror.org/03a1kwz48","country_code":"DE","type":"education","lineage":["https://openalex.org/I8087733"]}],"countries":["DE"],"is_corresponding":false,"raw_author_name":"Johannes Heidrich","raw_affiliation_strings":["Molecular Design and Pharmaceutical Biophysics, Institute of Pharmaceutical Sciences, Eberhard Karls University T\u00fcbingen, Auf der Morgenstelle 8, 72076 T\u00fcbingen, Germany"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Molecular Design and Pharmaceutical Biophysics, Institute of Pharmaceutical Sciences, Eberhard Karls University T\u00fcbingen, Auf der Morgenstelle 8, 72076 T\u00fcbingen, Germany","institution_ids":["https://openalex.org/I8087733"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5018032298","display_name":"Thomas E. Exner","orcid":"https://orcid.org/0000-0002-1849-5246"},"institutions":[{"id":"https://openalex.org/I8087733","display_name":"University of T\u00fcbingen","ror":"https://ror.org/03a1kwz48","country_code":"DE","type":"education","lineage":["https://openalex.org/I8087733"]}],"countries":["DE"],"is_corresponding":false,"raw_author_name":"Thomas E. Exner","raw_affiliation_strings":["Center for Bioinformatics T\u00fcbingen (ZBIT), Eberhard Karls University T\u00fcbingen, Sand 1, 72076 T\u00fcbingen, Germany","Molecular Design and Pharmaceutical Biophysics, Institute of Pharmaceutical Sciences, Eberhard Karls University T\u00fcbingen, Auf der Morgenstelle 8, 72076 T\u00fcbingen, Germany"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Center for Bioinformatics T\u00fcbingen (ZBIT), Eberhard Karls University T\u00fcbingen, Sand 1, 72076 T\u00fcbingen, Germany","institution_ids":["https://openalex.org/I8087733"]},{"raw_affiliation_string":"Molecular Design and Pharmaceutical Biophysics, Institute of Pharmaceutical Sciences, Eberhard Karls University T\u00fcbingen, Auf der Morgenstelle 8, 72076 T\u00fcbingen, Germany","institution_ids":["https://openalex.org/I8087733"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5086525697","display_name":"Frank M. Boeckler","orcid":"https://orcid.org/0000-0001-8738-6716"},"institutions":[{"id":"https://openalex.org/I8087733","display_name":"University of T\u00fcbingen","ror":"https://ror.org/03a1kwz48","country_code":"DE","type":"education","lineage":["https://openalex.org/I8087733"]}],"countries":["DE"],"is_corresponding":true,"raw_author_name":"Frank M. Boeckler","raw_affiliation_strings":["Center for Bioinformatics T\u00fcbingen (ZBIT), Eberhard Karls University T\u00fcbingen, Sand 1, 72076 T\u00fcbingen, Germany","Molecular Design and Pharmaceutical Biophysics, Institute of Pharmaceutical Sciences, Eberhard Karls University T\u00fcbingen, Auf der Morgenstelle 8, 72076 T\u00fcbingen, Germany"],"raw_orcid":"https://orcid.org/0000-0001-8738-6716","affiliations":[{"raw_affiliation_string":"Center for Bioinformatics T\u00fcbingen (ZBIT), Eberhard Karls University T\u00fcbingen, Sand 1, 72076 T\u00fcbingen, Germany","institution_ids":["https://openalex.org/I8087733"]},{"raw_affiliation_string":"Molecular Design and Pharmaceutical Biophysics, Institute of Pharmaceutical Sciences, Eberhard Karls University T\u00fcbingen, Auf der Morgenstelle 8, 72076 T\u00fcbingen, Germany","institution_ids":["https://openalex.org/I8087733"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5086525697"],"corresponding_institution_ids":["https://openalex.org/I8087733"],"apc_list":null,"apc_paid":null,"fwci":2.0812,"has_fulltext":false,"cited_by_count":18,"citation_normalized_percentile":{"value":0.87498748,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"59","issue":"2","first_page":"636","last_page":"643"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10798","display_name":"Crystallography and molecular interactions","score":1.0,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T10798","display_name":"Crystallography and molecular interactions","score":1.0,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12356","display_name":"Bioactive Compounds and Antitumor Agents","score":0.9976999759674072,"subfield":{"id":"https://openalex.org/subfields/3005","display_name":"Toxicology"},"field":{"id":"https://openalex.org/fields/30","display_name":"Pharmacology, Toxicology and Pharmaceutics"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T12893","display_name":"Organic Chemistry Cycloaddition Reactions","score":0.996399998664856,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"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/halogen","display_name":"Halogen","score":0.6263023018836975},{"id":"https://openalex.org/keywords/magnitude","display_name":"Magnitude (astronomy)","score":0.5363356471061707},{"id":"https://openalex.org/keywords/drug-discovery","display_name":"Drug discovery","score":0.5037814974784851},{"id":"https://openalex.org/keywords/chemistry","display_name":"Chemistry","score":0.43311771750450134},{"id":"https://openalex.org/keywords/computer-science","display_name":"Computer science","score":0.36049917340278625},{"id":"https://openalex.org/keywords/combinatorial-chemistry","display_name":"Combinatorial chemistry","score":0.320412278175354},{"id":"https://openalex.org/keywords/organic-chemistry","display_name":"Organic chemistry","score":0.17031508684158325},{"id":"https://openalex.org/keywords/physics","display_name":"Physics","score":0.14661037921905518}],"concepts":[{"id":"https://openalex.org/C46062151","wikidata":"https://www.wikidata.org/wiki/Q19605","display_name":"Halogen","level":3,"score":0.6263023018836975},{"id":"https://openalex.org/C126691448","wikidata":"https://www.wikidata.org/wiki/Q2028919","display_name":"Magnitude (astronomy)","level":2,"score":0.5363356471061707},{"id":"https://openalex.org/C74187038","wikidata":"https://www.wikidata.org/wiki/Q1418791","display_name":"Drug discovery","level":2,"score":0.5037814974784851},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.43311771750450134},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.36049917340278625},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.320412278175354},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.17031508684158325},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.14661037921905518},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.0},{"id":"https://openalex.org/C1276947","wikidata":"https://www.wikidata.org/wiki/Q333","display_name":"Astronomy","level":1,"score":0.0},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D006219","descriptor_name":"Halogens","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D006219","descriptor_name":"Halogens","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D006219","descriptor_name":"Halogens","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D008958","descriptor_name":"Models, Molecular","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008958","descriptor_name":"Models, Molecular","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008958","descriptor_name":"Models, Molecular","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008968","descriptor_name":"Molecular Conformation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008968","descriptor_name":"Molecular Conformation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D008968","descriptor_name":"Molecular Conformation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D011789","descriptor_name":"Quantum Theory","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D011789","descriptor_name":"Quantum Theory","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D011789","descriptor_name":"Quantum Theory","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D013997","descriptor_name":"Time Factors","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013997","descriptor_name":"Time Factors","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D013997","descriptor_name":"Time Factors","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D055808","descriptor_name":"Drug Discovery","qualifier_ui":"Q000379","qualifier_name":"methods","is_major_topic":false},{"descriptor_ui":"D055808","descriptor_name":"Drug Discovery","qualifier_ui":"Q000379","qualifier_name":"methods","is_major_topic":false},{"descriptor_ui":"D055808","descriptor_name":"Drug Discovery","qualifier_ui":"Q000379","qualifier_name":"methods","is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/acs.jcim.8b00622","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.jcim.8b00622","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:30582814","is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/30582814","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":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":47,"referenced_works":["https://openalex.org/W112873001","https://openalex.org/W166331879","https://openalex.org/W421463624","https://openalex.org/W1548914255","https://openalex.org/W1570448133","https://openalex.org/W1982346259","https://openalex.org/W1989333060","https://openalex.org/W1989765844","https://openalex.org/W1990724722","https://openalex.org/W1993289010","https://openalex.org/W1993311612","https://openalex.org/W2001964040","https://openalex.org/W2016373164","https://openalex.org/W2027392184","https://openalex.org/W2027423337","https://openalex.org/W2030841140","https://openalex.org/W2037489885","https://openalex.org/W2059107251","https://openalex.org/W2063021257","https://openalex.org/W2073841784","https://openalex.org/W2078641649","https://openalex.org/W2083084862","https://openalex.org/W2083752746","https://openalex.org/W2088999061","https://openalex.org/W2090157995","https://openalex.org/W2098889731","https://openalex.org/W2133534988","https://openalex.org/W2148797284","https://openalex.org/W2161205137","https://openalex.org/W2262253939","https://openalex.org/W2262964563","https://openalex.org/W2301699158","https://openalex.org/W2322081414","https://openalex.org/W2329413911","https://openalex.org/W2464571536","https://openalex.org/W2551206841","https://openalex.org/W2598562732","https://openalex.org/W2600906272","https://openalex.org/W2612165367","https://openalex.org/W2749566554","https://openalex.org/W2766685103","https://openalex.org/W2767744242","https://openalex.org/W2809522080","https://openalex.org/W2910129405","https://openalex.org/W2916720441","https://openalex.org/W4230096730","https://openalex.org/W4255434014"],"related_works":["https://openalex.org/W4387497383","https://openalex.org/W2948807893","https://openalex.org/W2778153218","https://openalex.org/W2748952813","https://openalex.org/W1531601525","https://openalex.org/W4391375266","https://openalex.org/W2078814861","https://openalex.org/W2527526854","https://openalex.org/W1976181487","https://openalex.org/W2063700634"],"abstract_inverted_index":{"Halogen":[0],"bonding":[1],"as":[2,132],"a":[3,27,54,67,74,156,179,189,193],"modern":[4],"molecular":[5,45],"interaction":[6,87],"has":[7,128],"received":[8],"increasing":[9],"attention":[10],"not":[11,165],"only":[12],"in":[13,18,44,172],"materials":[14],"sciences":[15],"but":[16],"also":[17],"biological":[19],"systems":[20],"and":[21,33,47,70,89,111,142,163],"drug":[22,173],"discovery.":[23],"Thus,":[24],"there":[25],"is":[26,57,161,216],"growing":[28],"demand":[29],"for":[30,136,167,181],"fast,":[31],"efficient,":[32],"easily":[34],"applicable":[35,166],"tailor-made":[36],"tools":[37],"supporting":[38],"the":[39,63,71,83,86,90,98,101,121,126,133,137,140,143,146,182,209,212],"use":[40],"of":[41,53,62,85,92,100,139,145,150,159,170,184,195,200],"halogen":[42,55,147],"bonds":[43],"design":[46],"medicinal":[48],"chemistry.":[49],"The":[50,115],"potential":[51,119],"strength":[52,144],"bond":[56],"dependent":[58],"on":[59,97,120,188],"several":[60],"properties":[61],"\u03c3-hole":[64,72,102,141],"donor,":[65],"e.g.,":[66],"(hetero)aryl":[68],"halide,":[69],"acceptor,":[73,93],"nucleophile":[75],"with":[76,192],"n":[77],"or":[78],"\u03c0":[79],"electron":[80],"density.":[81],"Besides":[82],"influence":[84],"geometry":[88],"type":[91],"significant":[94],"tuning":[95],"effects":[96],"magnitude":[99,138,201],"can":[103],"be":[104],"observed,":[105],"caused":[106],"by":[107],"different":[108],"(hetero)aromatic":[109],"scaffolds":[110],"their":[112],"substitution":[113],"patterns.":[114],"most":[116],"positive":[117],"electrostatic":[118],"isodensity":[122],"surface":[123],"(Vmax),":[124],"representing":[125],"\u03c3-hole,":[127],"been":[129],"widely":[130],"used":[131],"standard":[134],"descriptor":[135,186],"bond.":[148],"Calculation":[149],"Vmax":[151],"using":[152],"quantum-mechanical":[153,205],"methods":[154],"at":[155],"reasonable":[157],"level":[158],"theory":[160],"time-consuming":[162],"thus":[164],"larger":[168],"numbers":[169],"compounds":[171],"discovery":[174],"projects.":[175],"Herein":[176],"we":[177],"present":[178],"tool":[180],"prediction":[183],"this":[185],"based":[187],"machine-learned":[190],"model":[191],"speedup":[194],"5":[196],"to":[197,203,208],"6":[198],"orders":[199],"relative":[202],"MP2":[204],"calculations.":[206],"According":[207],"test":[210],"set,":[211],"squared":[213],"correlation":[214],"coefficient":[215],"greater":[217],"than":[218],"0.94.":[219]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":5}],"updated_date":"2026-05-19T08:33:51.333923","created_date":"2025-10-10T00:00:00"}
