{"id":"https://openalex.org/W2016055343","doi":"https://doi.org/10.1021/ci990149y","title":"Identification of Groupings of Graph Theoretical Molecular Descriptors Using a Hybrid Cluster Analysis Approach","display_name":"Identification of Groupings of Graph Theoretical Molecular Descriptors Using a Hybrid Cluster Analysis Approach","publication_year":2000,"publication_date":"2000-08-26","ids":{"openalex":"https://openalex.org/W2016055343","doi":"https://doi.org/10.1021/ci990149y","mag":"2016055343","pmid":"https://pubmed.ncbi.nlm.nih.gov/11045805"},"language":"en","primary_location":{"id":"doi:10.1021/ci990149y","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ci990149y","pdf_url":null,"source":{"id":"https://openalex.org/S171559003","display_name":"Journal of Chemical Information and Computer Sciences","issn_l":"0095-2338","issn":["0095-2338","1520-5142"],"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 Computer Sciences","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/A5091406016","display_name":"Stavros Taraviras","orcid":"https://orcid.org/0000-0002-7455-647X"},"institutions":[{"id":"https://openalex.org/I201841394","display_name":"Universit\u00e9 C\u00f4te d'Azur","ror":"https://ror.org/019tgvf94","country_code":"FR","type":"education","lineage":["https://openalex.org/I201841394"]}],"countries":["FR"],"is_corresponding":true,"raw_author_name":"Stavros L. Taraviras","raw_affiliation_strings":["Chimiometry and Molecular Modeling Group, Ar\u00f4mes, Synth\u00e8ses et Interactions Lab, University of Nice-Sophia Antipolis, 28 Avenue Valrose, 06108 Nice Cedex 2, France, and Department of Organic Chemistry, Faculty of Chemical Technology, University \u201cPolitehnica\u201d of Bucharest, Oficiul 12 CP 243, 78100 Bucharest, Romania"],"affiliations":[{"raw_affiliation_string":"Chimiometry and Molecular Modeling Group, Ar\u00f4mes, Synth\u00e8ses et Interactions Lab, University of Nice-Sophia Antipolis, 28 Avenue Valrose, 06108 Nice Cedex 2, France, and Department of Organic Chemistry, Faculty of Chemical Technology, University \u201cPolitehnica\u201d of Bucharest, Oficiul 12 CP 243, 78100 Bucharest, Romania","institution_ids":["https://openalex.org/I201841394"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5006473765","display_name":"Ovidiu Ivanciuc","orcid":null},"institutions":[{"id":"https://openalex.org/I201841394","display_name":"Universit\u00e9 C\u00f4te d'Azur","ror":"https://ror.org/019tgvf94","country_code":"FR","type":"education","lineage":["https://openalex.org/I201841394"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Ovidiu Ivanciuc","raw_affiliation_strings":["Chimiometry and Molecular Modeling Group, Ar\u00f4mes, Synth\u00e8ses et Interactions Lab, University of Nice-Sophia Antipolis, 28 Avenue Valrose, 06108 Nice Cedex 2, France, and Department of Organic Chemistry, Faculty of Chemical Technology, University \u201cPolitehnica\u201d of Bucharest, Oficiul 12 CP 243, 78100 Bucharest, Romania"],"affiliations":[{"raw_affiliation_string":"Chimiometry and Molecular Modeling Group, Ar\u00f4mes, Synth\u00e8ses et Interactions Lab, University of Nice-Sophia Antipolis, 28 Avenue Valrose, 06108 Nice Cedex 2, France, and Department of Organic Chemistry, Faculty of Chemical Technology, University \u201cPolitehnica\u201d of Bucharest, Oficiul 12 CP 243, 78100 Bucharest, Romania","institution_ids":["https://openalex.org/I201841394"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5040646066","display_name":"Daniel Cabrol\u2010Bass","orcid":null},"institutions":[{"id":"https://openalex.org/I201841394","display_name":"Universit\u00e9 C\u00f4te d'Azur","ror":"https://ror.org/019tgvf94","country_code":"FR","type":"education","lineage":["https://openalex.org/I201841394"]}],"countries":["FR"],"is_corresponding":false,"raw_author_name":"Daniel Cabrol-Bass","raw_affiliation_strings":["Chimiometry and Molecular Modeling Group, Ar\u00f4mes, Synth\u00e8ses et Interactions Lab, University of Nice-Sophia Antipolis, 28 Avenue Valrose, 06108 Nice Cedex 2, France, and Department of Organic Chemistry, Faculty of Chemical Technology, University \u201cPolitehnica\u201d of Bucharest, Oficiul 12 CP 243, 78100 Bucharest, Romania"],"affiliations":[{"raw_affiliation_string":"Chimiometry and Molecular Modeling Group, Ar\u00f4mes, Synth\u00e8ses et Interactions Lab, University of Nice-Sophia Antipolis, 28 Avenue Valrose, 06108 Nice Cedex 2, France, and Department of Organic Chemistry, Faculty of Chemical Technology, University \u201cPolitehnica\u201d of Bucharest, Oficiul 12 CP 243, 78100 Bucharest, Romania","institution_ids":["https://openalex.org/I201841394"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5091406016"],"corresponding_institution_ids":["https://openalex.org/I201841394"],"apc_list":null,"apc_paid":null,"fwci":4.9961,"has_fulltext":false,"cited_by_count":23,"citation_normalized_percentile":{"value":0.95501245,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":89,"max":94},"biblio":{"volume":"40","issue":"5","first_page":"1128","last_page":"1146"},"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/T13013","display_name":"Free Radicals and Antioxidants","score":0.9603999853134155,"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"}},{"id":"https://openalex.org/T11882","display_name":"Plant biochemistry and biosynthesis","score":0.9581000208854675,"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"}}],"keywords":[{"id":"https://openalex.org/keywords/principal-component-analysis","display_name":"Principal component analysis","score":0.776358962059021},{"id":"https://openalex.org/keywords/weighting","display_name":"Weighting","score":0.7588343620300293},{"id":"https://openalex.org/keywords/cluster-analysis","display_name":"Cluster analysis","score":0.5884496569633484},{"id":"https://openalex.org/keywords/graph","display_name":"Graph","score":0.5542840957641602},{"id":"https://openalex.org/keywords/identification","display_name":"Identification (biology)","score":0.55158931016922},{"id":"https://openalex.org/keywords/molecular-descriptor","display_name":"Molecular descriptor","score":0.5357953906059265},{"id":"https://openalex.org/keywords/computer-science","display_name":"Computer science","score":0.5059136748313904},{"id":"https://openalex.org/keywords/data-mining","display_name":"Data mining","score":0.49505415558815},{"id":"https://openalex.org/keywords/computation","display_name":"Computation","score":0.4937015473842621},{"id":"https://openalex.org/keywords/pattern-recognition","display_name":"Pattern recognition (psychology)","score":0.49084073305130005},{"id":"https://openalex.org/keywords/cluster","display_name":"Cluster (spacecraft)","score":0.49060288071632385},{"id":"https://openalex.org/keywords/artificial-intelligence","display_name":"Artificial intelligence","score":0.4115203022956848},{"id":"https://openalex.org/keywords/mathematics","display_name":"Mathematics","score":0.36975523829460144},{"id":"https://openalex.org/keywords/algorithm","display_name":"Algorithm","score":0.27792710065841675},{"id":"https://openalex.org/keywords/machine-learning","display_name":"Machine learning","score":0.24012181162834167},{"id":"https://openalex.org/keywords/theoretical-computer-science","display_name":"Theoretical computer science","score":0.1922939419746399},{"id":"https://openalex.org/keywords/quantitative-structure\u2013activity-relationship","display_name":"Quantitative structure\u2013activity relationship","score":0.12419307231903076}],"concepts":[{"id":"https://openalex.org/C27438332","wikidata":"https://www.wikidata.org/wiki/Q2873","display_name":"Principal component analysis","level":2,"score":0.776358962059021},{"id":"https://openalex.org/C183115368","wikidata":"https://www.wikidata.org/wiki/Q856577","display_name":"Weighting","level":2,"score":0.7588343620300293},{"id":"https://openalex.org/C73555534","wikidata":"https://www.wikidata.org/wiki/Q622825","display_name":"Cluster analysis","level":2,"score":0.5884496569633484},{"id":"https://openalex.org/C132525143","wikidata":"https://www.wikidata.org/wiki/Q141488","display_name":"Graph","level":2,"score":0.5542840957641602},{"id":"https://openalex.org/C116834253","wikidata":"https://www.wikidata.org/wiki/Q2039217","display_name":"Identification (biology)","level":2,"score":0.55158931016922},{"id":"https://openalex.org/C164923092","wikidata":"https://www.wikidata.org/wiki/Q3705921","display_name":"Molecular descriptor","level":3,"score":0.5357953906059265},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.5059136748313904},{"id":"https://openalex.org/C124101348","wikidata":"https://www.wikidata.org/wiki/Q172491","display_name":"Data mining","level":1,"score":0.49505415558815},{"id":"https://openalex.org/C45374587","wikidata":"https://www.wikidata.org/wiki/Q12525525","display_name":"Computation","level":2,"score":0.4937015473842621},{"id":"https://openalex.org/C153180895","wikidata":"https://www.wikidata.org/wiki/Q7148389","display_name":"Pattern recognition (psychology)","level":2,"score":0.49084073305130005},{"id":"https://openalex.org/C164866538","wikidata":"https://www.wikidata.org/wiki/Q367351","display_name":"Cluster (spacecraft)","level":2,"score":0.49060288071632385},{"id":"https://openalex.org/C154945302","wikidata":"https://www.wikidata.org/wiki/Q11660","display_name":"Artificial intelligence","level":1,"score":0.4115203022956848},{"id":"https://openalex.org/C33923547","wikidata":"https://www.wikidata.org/wiki/Q395","display_name":"Mathematics","level":0,"score":0.36975523829460144},{"id":"https://openalex.org/C11413529","wikidata":"https://www.wikidata.org/wiki/Q8366","display_name":"Algorithm","level":1,"score":0.27792710065841675},{"id":"https://openalex.org/C119857082","wikidata":"https://www.wikidata.org/wiki/Q2539","display_name":"Machine learning","level":1,"score":0.24012181162834167},{"id":"https://openalex.org/C80444323","wikidata":"https://www.wikidata.org/wiki/Q2878974","display_name":"Theoretical computer science","level":1,"score":0.1922939419746399},{"id":"https://openalex.org/C164126121","wikidata":"https://www.wikidata.org/wiki/Q766383","display_name":"Quantitative structure\u2013activity relationship","level":2,"score":0.12419307231903076},{"id":"https://openalex.org/C126838900","wikidata":"https://www.wikidata.org/wiki/Q77604","display_name":"Radiology","level":1,"score":0.0},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.0},{"id":"https://openalex.org/C59822182","wikidata":"https://www.wikidata.org/wiki/Q441","display_name":"Botany","level":1,"score":0.0},{"id":"https://openalex.org/C71924100","wikidata":"https://www.wikidata.org/wiki/Q11190","display_name":"Medicine","level":0,"score":0.0},{"id":"https://openalex.org/C199360897","wikidata":"https://www.wikidata.org/wiki/Q9143","display_name":"Programming language","level":1,"score":0.0}],"mesh":[{"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":"D016000","descriptor_name":"Cluster Analysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D016000","descriptor_name":"Cluster Analysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D016000","descriptor_name":"Cluster Analysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D020650","descriptor_name":"Combinatorial Chemistry Techniques","qualifier_ui":"Q000379","qualifier_name":"methods","is_major_topic":false},{"descriptor_ui":"D020650","descriptor_name":"Combinatorial Chemistry Techniques","qualifier_ui":"Q000379","qualifier_name":"methods","is_major_topic":false},{"descriptor_ui":"D020650","descriptor_name":"Combinatorial Chemistry Techniques","qualifier_ui":"Q000379","qualifier_name":"methods","is_major_topic":false},{"descriptor_ui":"D021281","descriptor_name":"Quantitative Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D021281","descriptor_name":"Quantitative Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D021281","descriptor_name":"Quantitative Structure-Activity Relationship","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true}],"locations_count":2,"locations":[{"id":"doi:10.1021/ci990149y","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ci990149y","pdf_url":null,"source":{"id":"https://openalex.org/S171559003","display_name":"Journal of Chemical Information and Computer Sciences","issn_l":"0095-2338","issn":["0095-2338","1520-5142"],"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 Computer Sciences","raw_type":"journal-article"},{"id":"pmid:11045805","is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/11045805","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 computer sciences","raw_type":null}],"best_oa_location":null,"sustainable_development_goals":[{"score":0.75,"display_name":"Reduced inequalities","id":"https://metadata.un.org/sdg/10"}],"awards":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":60,"referenced_works":["https://openalex.org/W40229915","https://openalex.org/W599997389","https://openalex.org/W623814603","https://openalex.org/W649490286","https://openalex.org/W1488799823","https://openalex.org/W1493454437","https://openalex.org/W1500959893","https://openalex.org/W1501730368","https://openalex.org/W1585772109","https://openalex.org/W1594341127","https://openalex.org/W1605923270","https://openalex.org/W1963752964","https://openalex.org/W1965573711","https://openalex.org/W1966715677","https://openalex.org/W1970936511","https://openalex.org/W1972327596","https://openalex.org/W1981214699","https://openalex.org/W1984112688","https://openalex.org/W1991938983","https://openalex.org/W1999249079","https://openalex.org/W2000868500","https://openalex.org/W2005685204","https://openalex.org/W2006028730","https://openalex.org/W2011179145","https://openalex.org/W2016381774","https://openalex.org/W2016496752","https://openalex.org/W2021083597","https://openalex.org/W2022491718","https://openalex.org/W2022701930","https://openalex.org/W2026513874","https://openalex.org/W2026909852","https://openalex.org/W2034411740","https://openalex.org/W2037319728","https://openalex.org/W2041905826","https://openalex.org/W2058444859","https://openalex.org/W2079967481","https://openalex.org/W2081050523","https://openalex.org/W2083468430","https://openalex.org/W2084134149","https://openalex.org/W2086920981","https://openalex.org/W2089923519","https://openalex.org/W2094718848","https://openalex.org/W2096729078","https://openalex.org/W2118587067","https://openalex.org/W2122000960","https://openalex.org/W2124507222","https://openalex.org/W2229908198","https://openalex.org/W2283313207","https://openalex.org/W2471648104","https://openalex.org/W2530689365","https://openalex.org/W2612166593","https://openalex.org/W2627054538","https://openalex.org/W2766967542","https://openalex.org/W2949435151","https://openalex.org/W2993383518","https://openalex.org/W3017143921","https://openalex.org/W3142152711","https://openalex.org/W3147295069","https://openalex.org/W4285719527","https://openalex.org/W4301194639"],"related_works":["https://openalex.org/W2380927352","https://openalex.org/W3178621026","https://openalex.org/W2137598809","https://openalex.org/W2085553065","https://openalex.org/W4211209597","https://openalex.org/W2874540278","https://openalex.org/W3048981730","https://openalex.org/W2018199316","https://openalex.org/W2138351929","https://openalex.org/W1485954976"],"abstract_inverted_index":{"There":[0],"is":[1,61],"an":[2,113],"abundance":[3],"of":[4,8,31,44,57,78,90,134,144,197,218],"structural":[5,46],"molecular":[6,32,53],"descriptors":[7,23,65,91,97,178,198],"various":[9],"forms":[10],"that":[11,48,63],"have":[12,37],"been":[13],"proposed":[14],"and":[15,72,92,142,160,193,212],"tested":[16],"over":[17],"the":[18,28,42,52,70,73,79,88,132,166,169,188,194,204,207,216],"years.":[19],"Very":[20],"often":[21],"different":[22,45,145,189,208],"represent,":[24],"more":[25],"or":[26,55,103],"less,":[27],"same":[29],"aspects":[30],"structures":[33],"and,":[34],"thus,":[35],"they":[36],"diminished":[38],"discriminating":[39],"power":[40],"for":[41,86,115,126,184,202,215],"identification":[43],"features":[47],"might":[49],"contribute":[50],"to":[51,68,156],"property,":[54],"activity":[56],"interest.":[58],"Therefore,":[59],"it":[60],"essential":[62],"noncorrelated":[64,94],"be":[66],"employed":[67],"ensure":[69],"wider":[71],"less":[74],"inflated":[75],"possible":[76],"coverage":[77],"chemical":[80],"space.":[81],"The":[82,173],"most":[83],"usual":[84],"approach":[85,114],"reducing":[87],"number":[89],"employing":[93],"(or":[95],"orthogonal)":[96],"involves":[98],"principal":[99],"component":[100],"analysis":[101,136],"(PCA)":[102],"other":[104],"factor":[105],"analytical":[106],"techniques.":[107],"In":[108],"this":[109],"work":[110],"we":[111],"present":[112],"determining":[116],"relationships":[117],"(groupings)":[118],"among":[119],"240":[120],"graph-theoretical":[121],"descriptors,":[122],"as":[123,181],"a":[124,158,182,185],"means":[125],"selecting":[127],"nonredundant":[128],"ones,":[129],"based":[130],"on":[131,187],"application":[133],"cluster":[135],"(CA).":[137],"To":[138],"remove":[139],"inherent":[140],"biases":[141],"particularities":[143],"CA":[146,190],"algorithms,":[147,153],"several":[148],"clustering":[149],"solutions,":[150],"using":[151],"these":[152,219],"were":[154,179,199],"\"hybridized\"":[155],"obtain":[157],"reliable":[159],"confident":[161],"overall":[162],"solution":[163],"concerning":[164],"how":[165],"interrelationships":[167],"within":[168],"data":[170],"are":[171],"structured.":[172],"calculated":[174],"correlation":[175],"coefficients":[176],"between":[177,206],"used":[180,214],"reference":[183],"discussion":[186],"methods":[191],"employed,":[192],"resulted":[195],"clusters":[196],"statistically":[200],"analyzed":[201],"deriving":[203],"intercorrelations":[205],"operators,":[209],"weighting":[210],"schemes":[211],"matrices":[213],"computation":[217],"descriptors.":[220]},"counts_by_year":[{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":1}],"updated_date":"2025-11-06T03:46:38.306776","created_date":"2025-10-10T00:00:00"}