{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T19:53:31Z","timestamp":1762113211565},"reference-count":46,"publisher":"Springer Science and Business Media LLC","issue":"6-7","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J Comput Aided Mol Des"],"published-print":{"date-parts":[[2010,6]]},"DOI":"10.1007\/s10822-010-9344-6","type":"journal-article","created":{"date-parts":[[2010,4,1]],"date-time":"2010-04-01T13:12:33Z","timestamp":1270127553000},"page":"627-638","source":"Crossref","is-referenced-by-count":12,"title":["Combinatorial\u2013computational\u2013chemoinformatics (C3) approach to finding and analyzing low-energy tautomers"],"prefix":"10.1007","volume":"24","author":[{"given":"Maciej","family":"Haranczyk","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maciej","family":"Gutowski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2010,4,2]]},"reference":[{"key":"9344_CR1","doi-asserted-by":"crossref","first-page":"3561","DOI":"10.1021\/cr030087h","volume":"105","author":"ED Raczynska","year":"2005","unstructured":"Raczynska ED, Kosinska W, Osmialowski B, Gawinecki R (2005) Chem Rev 105:3561\u20133612","journal-title":"Chem Rev"},{"key":"9344_CR2","unstructured":"Sayle R, Delany J (1999) Canonicalization and enumeration of tautomers, In: Innovative computational applications. Institute for International Research, Sir Francis Drake Hotel, San Francisco, 25\u201327 Oct 1999"},{"key":"9344_CR3","unstructured":"TAUTOMER, developed and distributed by Molecular networks GmbH, Erlangen, Germany"},{"key":"9344_CR4","doi-asserted-by":"crossref","first-page":"361","DOI":"10.1081\/RRS-120026975","volume":"23","author":"P Pospisil","year":"2003","unstructured":"Pospisil P, Ballmer P, Scapozza L, Folkers G (2003) J Recept Signal Transduct 23:361\u2013371","journal-title":"J Recept Signal Transduct"},{"key":"9344_CR5","doi-asserted-by":"crossref","first-page":"11495","DOI":"10.1021\/jp0535590","volume":"109","author":"M Haranczyk","year":"2005","unstructured":"Haranczyk M, Rak J, Gutowski M (2005) J Phys Chem A 109:11495\u201311503","journal-title":"J Phys Chem A"},{"key":"9344_CR6","doi-asserted-by":"crossref","first-page":"2116","DOI":"10.1039\/b503745j","volume":"7","author":"RA Bachorz","year":"2005","unstructured":"Bachorz RA, Rak J, Gutowski M (2005) Phys Chem Chem Phys 7:2116\u20132125","journal-title":"Phys Chem Chem Phys"},{"key":"9344_CR7","doi-asserted-by":"crossref","first-page":"24696","DOI":"10.1021\/jp065666f","volume":"110","author":"K Mazurkiewicz","year":"2006","unstructured":"Mazurkiewicz K, Bachorz RA, Gutowski M, Rak J (2006) J Phys Chem B 110:24696\u201324707","journal-title":"J Phys Chem B"},{"key":"9344_CR8","doi-asserted-by":"crossref","first-page":"7788","DOI":"10.1063\/1.471482","volume":"104","author":"JH Hendricks","year":"1996","unstructured":"Hendricks JH, Lyapustina SA, de Clercq HL, Snodgrass TJ, Bowen KH (1996) J Chem Phys 104:7788\u20137791","journal-title":"J Chem Phys"},{"key":"9344_CR9","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1140\/epjd\/e2002-00168-1","volume":"20","author":"M Gutowski","year":"2002","unstructured":"Gutowski M, D\u0105bkowska I, Rak J, Xu S, Nilles JM, Radisic D, Bowen KH Jr (2002) Eur Phys J D 20:431\u2013439","journal-title":"Eur Phys J D"},{"key":"9344_CR10","doi-asserted-by":"crossref","first-page":"7889","DOI":"10.1021\/jp034640a","volume":"107","author":"M Haranczyk","year":"2003","unstructured":"Haranczyk M, Bachorz RA, Rak J, Gutowski M, Radisic D, Stokes ST, Nilles JM, Bowen KH (2003) J Phys Chem B 107:7889\u20137895","journal-title":"J Phys Chem B"},{"key":"9344_CR11","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1560\/PBM0-CM9L-7YBH-W719","volume":"44","author":"M Haranczyk","year":"2004","unstructured":"Haranczyk M, Rak J, Gutowski M, Radisic D, Stokes ST, Nilles JM, Bowen KH Jr (2004) Israel J Chem 44:157\u2013170","journal-title":"Israel J Chem"},{"key":"9344_CR12","doi-asserted-by":"crossref","first-page":"6919","DOI":"10.1021\/jp0379143","volume":"108","author":"M Haranczyk","year":"2004","unstructured":"Haranczyk M, Dabkowska I, Rak J, Gutowski M, Nilles M, Stokes S, Radisic D, Bowen KH Jr (2004) J Phys Chem B 108:6919\u20136921","journal-title":"J Phys Chem B"},{"key":"9344_CR13","doi-asserted-by":"crossref","first-page":"13383","DOI":"10.1021\/jp050246w","volume":"109","author":"M Haranczyk","year":"2005","unstructured":"Haranczyk M, Rak J, Gutowski M, Radisic D, Stokes ST, Bowen KH Jr (2005) J Phys Chem B 109:13383\u201313391","journal-title":"J Phys Chem B"},{"key":"9344_CR14","unstructured":"In case on neutral NABs, canonical tautomer is either the most stable tautomer or among few most stable tautomers"},{"key":"9344_CR15","doi-asserted-by":"crossref","first-page":"686","DOI":"10.1021\/ci6002703","volume":"47","author":"M Haranczyk","year":"2007","unstructured":"Haranczyk M, Gutowski M (2007) J Chem Inf Model 47:686\u2013694","journal-title":"J Chem Inf Model"},{"key":"9344_CR16","unstructured":"Freely available at http:\/\/tautgen.sourceforge.net Accessed 25 Jan 2010"},{"key":"9344_CR17","doi-asserted-by":"crossref","first-page":"1596","DOI":"10.1021\/jp013337b","volume":"106","author":"X Li","year":"2002","unstructured":"Li X, Cai Z, Sevilla MD (2002) J Phys Chem A 106:1596\u20131603","journal-title":"J Phys Chem A"},{"key":"9344_CR18","doi-asserted-by":"crossref","first-page":"6585","DOI":"10.1002\/anie.200501671","volume":"44","author":"M Haranczyk","year":"2005","unstructured":"Haranczyk M, Gutowski M (2005) Angewandte Chemie Int Ed 44:6585\u20136588","journal-title":"Angewandte Chemie Int Ed"},{"key":"9344_CR19","doi-asserted-by":"crossref","first-page":"4804","DOI":"10.1073\/pnas.0609982104","volume":"104","author":"M Haranczyk","year":"2007","unstructured":"Haranczyk M, Gutowski M, Li X, Bowen KH Jr (2007) Proc Natl Acad Sci (PNAS) 104:4804\u20134807","journal-title":"Proc Natl Acad Sci (PNAS)"},{"key":"9344_CR20","doi-asserted-by":"crossref","first-page":"14073","DOI":"10.1021\/jp077439z","volume":"111","author":"M Haranczyk","year":"2007","unstructured":"Haranczyk M, Gutowski M, Li X, Bowen KH (2007) J Phys Chem B 111:14073\u201314076","journal-title":"J Phys Chem B"},{"key":"9344_CR21","doi-asserted-by":"crossref","first-page":"174309","DOI":"10.1063\/1.2795719","volume":"127","author":"X Li","year":"2007","unstructured":"Li X, Bowen KH, Haranczyk M, Bachorz RA, Mazurkiewicz K, Rak J, Gutowski M (2007) J Chem Phys 127:174309","journal-title":"J Chem Phys"},{"key":"9344_CR22","doi-asserted-by":"crossref","first-page":"1277","DOI":"10.1002\/jcc.20886","volume":"29","author":"M Haranczyk","year":"2008","unstructured":"Haranczyk M, Holliday J, Willett P, Gutowski M (2008) J Comput Chem 29:1277\u20131291","journal-title":"J Comput Chem"},{"key":"9344_CR23","doi-asserted-by":"crossref","first-page":"699","DOI":"10.1021\/ja046622s","volume":"127","author":"M Haranczyk","year":"2005","unstructured":"Haranczyk M, Gutowski M (2005) J Am Chem Soc (JACS) 127:699\u2013706","journal-title":"J Am Chem Soc (JACS)"},{"key":"9344_CR24","unstructured":"Taylor PR (1994) In: BO Roos (ed) Lecture notes in quantum chemistry II, Springer, Berlin"},{"key":"9344_CR25","unstructured":"Gaussian 03, Revision C.02, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JrJA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, and Pople JA, Gaussian Inc., Wallingford CT 2004"},{"key":"9344_CR26","unstructured":"Straatsma TP, Apr\u00e0 E, Windus TL, Bylaska EJ, de Jong W, Hirata S, Valiev M, Hackler M, Pollack L, Harrison R, Dupuis M, Smith DMA, Nieplocha J, Tipparaju V, Krishnan M, Auer AA, Brown E, Cisneros G, Fann G, Fr\u00fcchtl H, Garza J, Hirao K, Kendall R, Nichols J, Tsemekhman K, Wolinski K, Anchell J, Bernholdt D, Borowski P, Clark T, Clerc D, Dachsel H, Deegan M, Dyall K, Elwood D, Glendening E, Gutowski M, Hess A, Jaffe J, Johnson B, Ju J, Kobayashi R, Kutteh R, Lin Z, Littlefield R, Long X, Meng B, Nakajima T, Niu S, Rosing M, Sandrone G, Stave M, Taylor H, Thomas G, van Lenthe J, Wong A, Zhang Z, NWChem (2004) A computational chemistry package for parallel computers, Version 4.6, Pacific Northwest National Laboratory, Richland, Washington 99352-0999, USA"},{"key":"9344_CR27","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1016\/S0010-4655(00)00065-5","volume":"128","author":"RA Kendall","year":"2000","unstructured":"Kendall RA, Apr\u00e0 E, Bernholdt DE, Bylaska EJ, Dupuis M, Fann GI, Harrison RJ, Ju J, Nichols JA, Nieplocha J, Straatsma TP, Windus TL, Wong A (2000) Computer Phys Comm 128:260\u2013283","journal-title":"Computer Phys Comm"},{"key":"9344_CR28","doi-asserted-by":"crossref","first-page":"3098","DOI":"10.1103\/PhysRevA.38.3098","volume":"38","author":"AD Becke","year":"1988","unstructured":"Becke AD (1988) Phys Rev A 38:3098\u20133100","journal-title":"Phys Rev A"},{"key":"9344_CR29","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","volume":"98","author":"AD Becke","year":"1993","unstructured":"Becke AD (1993) J Chem Phys 98:5648\u20135652","journal-title":"J Chem Phys"},{"key":"9344_CR30","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","volume":"37","author":"C Lee","year":"1988","unstructured":"Lee C, Yang W, Paar RG (1988) Phys Rev B 37:785\u2013789","journal-title":"Phys Rev B"},{"key":"9344_CR31","doi-asserted-by":"crossref","first-page":"2027","DOI":"10.1021\/cr00031a013","volume":"94","author":"J Tomasi","year":"1994","unstructured":"Tomasi J, Persico M (1994) Chem Rev 94:2027\u20132094","journal-title":"Chem Rev"},{"key":"9344_CR32","unstructured":"GOT: Gaussian output tools available at http:\/\/gaussot.sf.net Accessed 25 Jan 2010"},{"key":"9344_CR33","doi-asserted-by":"crossref","unstructured":"Fogarasi G (2002) J Phys Chem A 106:1381\u20131390 and references cited therein","DOI":"10.1021\/jp013067x"},{"key":"9344_CR34","doi-asserted-by":"crossref","first-page":"6796","DOI":"10.1063\/1.462569","volume":"96","author":"RA Kendall","year":"1992","unstructured":"Kendall RA, Dunning TH Jr, Harrison RJ (1992) J Chem Phys 96:6796\u20136806","journal-title":"J Chem Phys"},{"key":"9344_CR35","unstructured":"Amos RD, Bernhardsson A, Berning A, Celani P, Cooper DL, Deegan MJO, Dobbyn AJ, Eckert F, Hampel C, Hetzer G, Knowles PJ, Korona T, Lindh R, Lloyd AW, McNicholas SJ, Manby FR, Meyer W, Mura ME, Nicklass A, Palmieri P, Pitzer R, Rauhut G, Sch\u00fctz M, Schumann U, Stoll H, Stone AJ, Tarroni R, Thorsteinsson T, Werner H-J, MOLPRO, a package of ab initio programs designed by H-J Werner and PJ Knowles, version 2002.1"},{"key":"9344_CR36","doi-asserted-by":"crossref","first-page":"085101","DOI":"10.1063\/1.2436890","volume":"126","author":"RA Bachorz","year":"2007","unstructured":"Bachorz RA, Klopper W, Gutowski M (2007) J Chem Phys 126:085101","journal-title":"J Chem Phys"},{"key":"9344_CR37","doi-asserted-by":"crossref","first-page":"5680","DOI":"10.1021\/jp711496y","volume":"112","author":"E Rosta","year":"2008","unstructured":"Rosta E, Haranczyk M, Chu ZT, Warshel A (2008) J Phys Chem B 112:5680\u20135692","journal-title":"J Phys Chem B"},{"key":"9344_CR38","doi-asserted-by":"crossref","first-page":"4442","DOI":"10.1039\/b802300j","volume":"10","author":"M Haranczyk","year":"2008","unstructured":"Haranczyk M, Gutowski M, Warshel A (2008) Phys Chem Chem Phys 10:4442\u20134448","journal-title":"Phys Chem Chem Phys"},{"key":"9344_CR39","doi-asserted-by":"crossref","first-page":"1253","DOI":"10.1021\/jp8071712","volume":"113","author":"S Kamerlin","year":"2009","unstructured":"Kamerlin S, Haranczyk M, Warshel A (2009) J Phys Chem B 113:1253\u20131272","journal-title":"J Phys Chem B"},{"key":"9344_CR40","doi-asserted-by":"crossref","first-page":"689","DOI":"10.1021\/ct800043a","volume":"4","author":"M Haranczyk","year":"2008","unstructured":"Haranczyk M, Gutowski M (2008) J Chem Theory Comput 4:689\u2013693","journal-title":"J Chem Theory Comput"},{"key":"9344_CR41","unstructured":"Open-source Cubefile Manipulator Program (OpenCubMan) is available free of charge at SourceForge archive: http:\/\/opencubman.sourceforge.net Accessed 15 Jan 2010"},{"key":"9344_CR42","doi-asserted-by":"crossref","first-page":"254","DOI":"10.1016\/j.commatsci.2005.04.010","volume":"36","author":"G Henkelman","year":"2006","unstructured":"Henkelman G, Arnaldsson A, J\u00f3nsson H (2006) Comput Mater Sci 36:254\u2013360","journal-title":"Comput Mater Sci"},{"key":"9344_CR43","doi-asserted-by":"crossref","first-page":"899","DOI":"10.1002\/jcc.20575","volume":"28","author":"E Sanville","year":"2007","unstructured":"Sanville E, Kenny SD, Smith R, Henkelman G (2007) J Comput Chem 28:899\u2013908","journal-title":"J Comput Chem"},{"key":"9344_CR44","first-page":"387","volume-title":"Atkins\u2019 physical chemistry","author":"P Atkins","year":"2006","unstructured":"Atkins P, De Paula J (2006) Atkins\u2019 physical chemistry, 8th edn. Oxford University Press, Oxford, p 387","edition":"8"},{"key":"9344_CR45","unstructured":"http:\/\/www.digitalchemistry.co.uk Accessed 25 Jan 2010"},{"key":"9344_CR46","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/j.theochem.2009.10.023","volume":"943","author":"T Mineva","year":"2010","unstructured":"Mineva T, Russo N (2010) J Mol Struct Theochem 943:71\u201376","journal-title":"J Mol Struct Theochem"}],"container-title":["Journal of Computer-Aided Molecular Design"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/www.springerlink.com\/index\/pdf\/10.1007\/s10822-010-9344-6","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2019,2,27]],"date-time":"2019-02-27T19:28:53Z","timestamp":1551295733000},"score":1,"resource":{"primary":{"URL":"http:\/\/link.springer.com\/10.1007\/s10822-010-9344-6"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2010,4,2]]},"references-count":46,"journal-issue":{"issue":"6-7","published-print":{"date-parts":[[2010,6]]}},"alternative-id":["9344"],"URL":"https:\/\/doi.org\/10.1007\/s10822-010-9344-6","relation":{},"ISSN":["0920-654X","1573-4951"],"issn-type":[{"value":"0920-654X","type":"print"},{"value":"1573-4951","type":"electronic"}],"subject":[],"published":{"date-parts":[[2010,4,2]]}}}