{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,14]],"date-time":"2026-03-14T11:43:48Z","timestamp":1773488628144,"version":"3.50.1"},"reference-count":78,"publisher":"American Chemical Society (ACS)","issue":"6","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Chem. Inf. Model."],"published-print":{"date-parts":[[2009,6,22]]},"DOI":"10.1021\/ci900085d","type":"journal-article","created":{"date-parts":[[2009,5,19]],"date-time":"2009-05-19T16:57:49Z","timestamp":1242752269000},"page":"1497-1513","source":"Crossref","is-referenced-by-count":32,"title":["Quantum Isostere Database: A Web-Based Tool Using Quantum Chemical Topology To Predict Bioisosteric Replacements for Drug Design"],"prefix":"10.1021","volume":"49","author":[{"given":"Mike","family":"Devereux","sequence":"first","affiliation":[{"name":"Manchester Interdisciplinary Biocentre (MIB), 131 Princess Street, Manchester M1 7DN, Great Britain, School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, Great Britain, and GlaxoSmithKline Medicines Research Centre, Computational and Structural Chemistry, Stevenage, Hertfordshire SG1 2NY, Great Britain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Paul L. A.","family":"Popelier","sequence":"additional","affiliation":[{"name":"Manchester Interdisciplinary Biocentre (MIB), 131 Princess Street, Manchester M1 7DN, Great Britain, School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, Great Britain, and GlaxoSmithKline Medicines Research Centre, Computational and Structural Chemistry, Stevenage, Hertfordshire SG1 2NY, Great Britain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Iain M.","family":"McLay","sequence":"additional","affiliation":[{"name":"Manchester Interdisciplinary Biocentre (MIB), 131 Princess Street, Manchester M1 7DN, Great Britain, School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, Great Britain, and GlaxoSmithKline Medicines Research Centre, Computational and Structural Chemistry, Stevenage, Hertfordshire SG1 2NY, Great Britain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"316","published-online":{"date-parts":[[2009,5,19]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"23","DOI":"10.2174\/0929867053363540","volume":"12","author":"Lima L. M.","year":"2005","journal-title":"Curr. Med. Chem."},{"issue":"8","key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"3147","DOI":"10.1021\/cr950066q","volume":"96","author":"Patani G. A.","year":"1996","journal-title":"Chem. Rev."},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1039\/cs9790800563","volume":"8","author":"Thornber C. W.","year":"1979","journal-title":"Chem. Soc. Rev."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1021\/ci0100806","volume":"42","author":"Sheridan R. P.","year":"2002","journal-title":"J. Chem. Inf. Comput. Sci."},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"677","DOI":"10.1021\/ci0503964","volume":"46","author":"Wagener M.","year":"2006","journal-title":"J. Chem. Inf. Model."},{"key":"ref6\/cit6","unstructured":"WDI, World Drug Index.Derwent Information; 1996."},{"key":"ref7\/cit7","doi-asserted-by":"crossref","DOI":"10.1093\/oso\/9780198551683.001.0001","volume-title":"Atoms in Molecules. A Quantum Theory","author":"Bader R. F. W.","year":"1990"},{"key":"ref8\/cit8","volume-title":"Atoms in Molecules. An Introduction","author":"Popelier P. L. A.","year":"2000"},{"key":"ref9\/cit9","first-page":"143","volume-title":"Chemical Modelling: Applications and Theory","author":"Popelier P. L. A.","year":"2000"},{"issue":"6","key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"620","DOI":"10.1002\/anie.199406201","volume":"33","author":"Bader R. F. W.","year":"1994","journal-title":"Angew. Chem., Int. Ed. Engl."},{"issue":"23","key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"5579","DOI":"10.1021\/jp9943631","volume":"104","author":"Bader R. F. W.","year":"2000","journal-title":"J. Phys. Chem. A"},{"issue":"5","key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"1169","DOI":"10.1080\/00268979600100781","volume":"87","author":"Popelier P. L. A.","year":"1996","journal-title":"Mol. Phys."},{"issue":"2","key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1016\/S0010-4655(97)00121-5","volume":"108","author":"Popelier P. L. A.","year":"1998","journal-title":"Comput. Phys. Commun."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"406","DOI":"10.1021\/ci025589v","volume":"43","author":"Holliday J. D.","year":"2003","journal-title":"J. Chem. Inf. Comput. Sci."},{"issue":"1","key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1002\/(SICI)1096-9063(199709)51:1<92::AID-PS608>3.0.CO;2-9","volume":"51","author":"Ujvary I.","year":"1997","journal-title":"Pestic. Sci."},{"key":"ref16\/cit16","volume-title":"DRAGON, version 2.1;","author":"Talete-srl; Todeschini R.","year":"2002"},{"key":"ref17\/cit17","volume-title":"SYBYL, Molecular Modeling Software, version 6.7"},{"key":"ref18\/cit18","volume-title":"Accelrys TSAR, version 3.3","year":"2005"},{"key":"ref19\/cit19","volume-title":"Accelrys CERIUS2, version 4.7","year":"2005"},{"issue":"1","key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/S1093-3263(98)00012-6","volume":"16","author":"Ertl P.","year":"1998","journal-title":"J. Mol. Graphics Modell."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"3257","DOI":"10.1021\/jm0300429","volume":"46","author":"Lewell X. Q.","year":"2003","journal-title":"J. Med. Chem."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"5959","DOI":"10.1021\/ja00226a005","volume":"110","author":"Cramer R. D.","year":"1988","journal-title":"J. Am. Chem. Soc."},{"issue":"23","key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"4502","DOI":"10.1021\/jm981037l","volume":"41","author":"Lemmen C.","year":"1998","journal-title":"J. Med. Chem."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"835","DOI":"10.1023\/A:1013115500749","volume":"15","author":"Watson P.","year":"2001","journal-title":"J. Comput.-Aided Mol. Des."},{"issue":"12","key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"903","DOI":"10.1023\/A:1023836420388","volume":"16","author":"Weber A.","year":"2002","journal-title":"J. Comput.-Aided Mol. Des."},{"issue":"6","key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1023\/A:1007934413448","volume":"11","author":"Bruno I. J.","year":"1997","journal-title":"J. Comput.-Aided Mol. Des."},{"key":"ref27\/cit27","first-page":"95","volume-title":"Computer-Assisted Lead Finding and Optimization","author":"Anzali S.","year":"1997"},{"key":"ref28\/cit28","volume-title":"BROOD","year":"2006"},{"key":"ref29\/cit29","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1021\/ci049651v","volume":"45","author":"Haigh J. A.","year":"2005","journal-title":"J. Chem. Inf. Model."},{"key":"ref30\/cit30","unstructured":"Daylight; Daylight Chemical Information Systems Inc.http:\/\/www.daylight.com."},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"1300","DOI":"10.1002\/jcc.21146","volume":"30","author":"Devereux M.","year":"2009","journal-title":"J. Comput. Chem."},{"key":"ref32\/cit32","volume-title":"Macromodel","year":"2005"},{"key":"ref33\/cit33","volume-title":"GAUSSIAN98, Gaussian 98, Revision A.7","author":"Frisch M. J.","year":"1998"},{"issue":"3","key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1002\/jcc.540030306","volume":"3","author":"Biegler-K\u00f6nig F. W.","year":"1982","journal-title":"J. Comput. Chem."},{"issue":"2","key":"ref35\/cit35","doi-asserted-by":"crossref","first-page":"212","DOI":"10.1016\/0010-4655(95)00113-1","volume":"93","author":"Popelier P. L. A.","year":"1996","journal-title":"Comput. Phys. Commun."},{"issue":"1","key":"ref36\/cit36","doi-asserted-by":"crossref","first-page":"160","DOI":"10.1016\/0009-2614(94)00897-3","volume":"228","author":"Popelier P. L. A.","year":"1994","journal-title":"Chem. Phys. Lett."},{"key":"ref37\/cit37","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1107\/S0108767304016228","volume":"60","author":"Popelier P. L. A.","year":"2004","journal-title":"Acta Crystallogr., Sect. A: Found. Crystallogr."},{"key":"ref38\/cit38","unstructured":"Oracle;Oracle Corporation:Redwood Shores, CA, 2005."},{"key":"ref39\/cit39","unstructured":"MySQL;Sun Microsystems Inc.:U.S.A., 2008."},{"key":"ref40\/cit40","unstructured":"CHIME Pro;Symyx Technologies.http:\/\/www.symyx.com."},{"key":"ref41\/cit41","doi-asserted-by":"crossref","first-page":"1262","DOI":"10.1021\/ci0003855","volume":"40","author":"Leach A. R.","year":"2000","journal-title":"J. Chem. Inf. Comput. Sci."},{"key":"ref42\/cit42","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1021\/j100785a001","volume":"68","author":"Bondi A.","year":"1964","journal-title":"J. Phys. Chem."},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1007\/BF01166045","volume":"3","author":"Johnson M. A.","year":"1989","journal-title":"J. Math. Chem."},{"key":"ref44\/cit44","volume-title":"IBM Internal Report 17th Nov.","author":"Tanimoto T. T.","year":"1957"},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"2747","DOI":"10.1039\/b102708p","volume":"3","author":"Lamarche O.","year":"2001","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref46\/cit46","doi-asserted-by":"crossref","first-page":"1595","DOI":"10.1039\/b816321a","volume":"11","author":"Devereux M.","year":"2009","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref47\/cit47","doi-asserted-by":"crossref","DOI":"10.1093\/oso\/9780198558842.001.0001","volume-title":"The Theory of Intermolecular Forces","author":"Stone A. J.","year":"1996"},{"key":"ref48\/cit48","doi-asserted-by":"crossref","DOI":"10.1093\/oso\/9780198551683.001.0001","volume-title":"Atom in Molecules. A Quantum Theory","author":"Bader R. F. W.","year":"1990"},{"key":"ref49\/cit49","doi-asserted-by":"crossref","first-page":"636","DOI":"10.1107\/S0108767394003077","volume":"50","author":"Su Z. W.","year":"1994","journal-title":"Acta Crystallogr., Sect. A: Found. Crystallogr."},{"issue":"8","key":"ref50\/cit50","doi-asserted-by":"crossref","first-page":"1440","DOI":"10.1139\/v90-220","volume":"68","author":"Sjoberg P.","year":"1990","journal-title":"Can. J. Chem."},{"issue":"4","key":"ref51\/cit51","doi-asserted-by":"crossref","first-page":"483","DOI":"10.1139\/v95-063","volume":"73","author":"Hagelin H.","year":"1995","journal-title":"Can. J. Chem."},{"issue":"5","key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"342","DOI":"10.1007\/s00894-003-0153-x","volume":"9","author":"Ehresmann B.","year":"2003","journal-title":"J. Mol. Model."},{"key":"ref53\/cit53","doi-asserted-by":"crossref","first-page":"973","DOI":"10.1039\/a908853i","volume":"2","author":"Platts J. A.","year":"2000","journal-title":"Phys. Chem. Chem. Phys."},{"issue":"6","key":"ref54\/cit54","doi-asserted-by":"crossref","first-page":"699","DOI":"10.1039\/p29890000699","author":"Abraham M. H.","year":"1989","journal-title":"J. Chem. Soc., Perkin Trans. 2"},{"issue":"4","key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1039\/p29900000521","author":"Abraham M. H.","year":"1990","journal-title":"J. Chem. Soc., Perkin Trans. 2"},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1016\/j.jmgm.2005.05.004","volume":"24","author":"Rafat M.","year":"2005","journal-title":"J. Mol. Graphics Modell."},{"key":"ref57\/cit57","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1021\/jo0347415","volume":"69","author":"Chaudry U. A.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref58\/cit58","first-page":"1231","volume":"2","author":"Popelier P. L. A.","year":"2002","journal-title":"J. Chem. Soc."},{"key":"ref59\/cit59","doi-asserted-by":"crossref","first-page":"862","DOI":"10.1016\/j.ejmech.2006.03.004","volume":"41","author":"Popelier P. L. A.","year":"2006","journal-title":"Eur. J. Med. Chem."},{"key":"ref60\/cit60","doi-asserted-by":"crossref","first-page":"3115","DOI":"10.1039\/b003026k","volume":"2","author":"Platts J. A.","year":"2000","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref61\/cit61","doi-asserted-by":"crossref","first-page":"835","DOI":"10.1021\/ci980339t","volume":"39","author":"Platts J. A.","year":"2000","journal-title":"J. Chem. Inf. Comput. Sci."},{"key":"ref62\/cit62","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1021\/ja00314a058","volume":"106","author":"Kamlet M. J.","year":"1984","journal-title":"J. Am. Chem. Soc."},{"issue":"2","key":"ref63\/cit63","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1039\/cs9932200073","volume":"22","author":"Abraham M. H.","year":"1993","journal-title":"Chem. Soc. Rev."},{"issue":"3","key":"ref64\/cit64","doi-asserted-by":"crossref","first-page":"161","DOI":"10.2174\/1389200054021799","volume":"6","author":"Kalgutkar A. S.","year":"2005","journal-title":"Curr. Drug Metab."},{"issue":"3","key":"ref65\/cit65","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1002\/jcc.540030306","volume":"3","author":"Biegler-K\u00f6nig F. W.","year":"1982","journal-title":"J. Comput. Chem."},{"issue":"5","key":"ref66\/cit66","doi-asserted-by":"crossref","first-page":"545","DOI":"10.1002\/1096-987X(20010415)22:5<545::AID-JCC1027>3.0.CO;2-Y","volume":"22","author":"Biegler-K\u00f6nig F.","year":"2001","journal-title":"J. Comput. Chem."},{"issue":"2","key":"ref67\/cit67","doi-asserted-by":"crossref","first-page":"304","DOI":"10.1021\/jp983362q","volume":"103","author":"Fradera X.","year":"1999","journal-title":"J. Phys. Chem. A"},{"issue":"6","key":"ref68\/cit68","doi-asserted-by":"crossref","first-page":"362","DOI":"10.1007\/s00214-002-0356-8","volume":"107","author":"Poater J.","year":"2002","journal-title":"Theor. Chem. Acc."},{"issue":"3","key":"ref69\/cit69","doi-asserted-by":"crossref","first-page":"379","DOI":"10.1002\/jcc.10188","volume":"24","author":"Wang Y. G.","year":"2003","journal-title":"J. Comput. Chem."},{"key":"ref70\/cit70","doi-asserted-by":"crossref","first-page":"304","DOI":"10.1021\/jp983362q","volume":"103","author":"Fradera X.","year":"1999","journal-title":"J. Phys. Chem. A"},{"issue":"20","key":"ref71\/cit71","doi-asserted-by":"crossref","first-page":"5244","DOI":"10.1021\/j100071a013","volume":"98","author":"Angyan J. G.","year":"1994","journal-title":"J. Phys. Chem."},{"issue":"3","key":"ref72\/cit72","doi-asserted-by":"crossref","first-page":"764","DOI":"10.1021\/jo9813944","volume":"64","author":"Salzner U.","year":"1999","journal-title":"J. Organomet. Chem."},{"issue":"20","key":"ref73\/cit73","doi-asserted-by":"crossref","first-page":"6634","DOI":"10.1021\/jo0492113","volume":"69","author":"Krygowski T. M.","year":"2004","journal-title":"J. Organomet. Chem."},{"issue":"22","key":"ref74\/cit74","doi-asserted-by":"crossref","first-page":"7537","DOI":"10.1021\/jo048988t","volume":"69","author":"Poater J.","year":"2004","journal-title":"J. Organomet. Chem."},{"issue":"6","key":"ref75\/cit75","doi-asserted-by":"crossref","first-page":"1215","DOI":"10.1139\/v96-136","volume":"74","author":"Laidig K. E.","year":"1996","journal-title":"Can. J. Chem."},{"key":"ref76\/cit76","first-page":"474","volume":"31","author":"Grimm H. G.","year":"1925","journal-title":"Z. Electrochem."},{"key":"ref77\/cit77","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.1002\/hlca.193201501132","volume":"15","author":"Erlenmeyer H.","year":"1932","journal-title":"Helv. Chim. Acta"},{"key":"ref78\/cit78","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1002\/qua.1625","volume":"86","author":"H\u00f6finger S.","year":"2002","journal-title":"Int. J. Quantum Chem."}],"container-title":["Journal of Chemical Information and Modeling"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ci900085d","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,2,9]],"date-time":"2025-02-09T15:50:55Z","timestamp":1739116255000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ci900085d"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,5,19]]},"references-count":78,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2009,6,22]]}},"alternative-id":["10.1021\/ci900085d"],"URL":"https:\/\/doi.org\/10.1021\/ci900085d","relation":{},"ISSN":["1549-9596","1549-960X"],"issn-type":[{"value":"1549-9596","type":"print"},{"value":"1549-960X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,5,19]]}}}