{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T10:46:42Z","timestamp":1760784402385,"version":"3.37.3"},"reference-count":31,"publisher":"Springer Science and Business Media LLC","issue":"2","license":[{"start":{"date-parts":[[2018,1,15]],"date-time":"2018-01-15T00:00:00Z","timestamp":1515974400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/www.springer.com\/tdm"}],"funder":[{"name":"National Brain Research Program","award":["KTIA NAP_13"],"award-info":[{"award-number":["KTIA NAP_13"]}]},{"DOI":"10.13039\/501100003549","name":"Orsz\u00e1gos Tudom\u00e1nyos Kutat\u00e1si Alapprogramok","doi-asserted-by":"publisher","award":["K111862"],"award-info":[{"award-number":["K111862"]}],"id":[{"id":"10.13039\/501100003549","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["J Comput Aided Mol Des"],"published-print":{"date-parts":[[2018,2]]},"DOI":"10.1007\/s10822-018-0097-y","type":"journal-article","created":{"date-parts":[[2018,1,14]],"date-time":"2018-01-14T23:22:42Z","timestamp":1515972162000},"page":"331-345","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Validation of tautomeric and protomeric binding modes by free energy calculations. A case study for the structure based optimization of d-amino acid oxidase inhibitors"],"prefix":"10.1007","volume":"32","author":[{"given":"Zolt\u00e1n","family":"Orgov\u00e1n","sequence":"first","affiliation":[]},{"given":"Gy\u00f6rgy G.","family":"Ferenczy","sequence":"additional","affiliation":[]},{"given":"Thomas","family":"Steinbrecher","sequence":"additional","affiliation":[]},{"given":"Bence","family":"Szil\u00e1gyi","sequence":"additional","affiliation":[]},{"given":"D\u00e1vid","family":"Bajusz","sequence":"additional","affiliation":[]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1039-7809","authenticated-orcid":false,"given":"Gy\u00f6rgy M.","family":"Keser\u0171","sequence":"additional","affiliation":[]}],"member":"297","published-online":{"date-parts":[[2018,1,15]]},"reference":[{"issue":"4","key":"97_CR1","doi-asserted-by":"publisher","first-page":"405","DOI":"10.1038\/sj.mp.4001012","volume":"7","author":"JA Badner","year":"2002","unstructured":"Badner JA, Gershon ES (2002) Meta-analysis of whole-genome linkage scans of bipolar disorder and schizophrenia. Mol Psychiatry 7(4):405\u2013411","journal-title":"Mol Psychiatry"},{"issue":"7","key":"97_CR2","doi-asserted-by":"publisher","first-page":"658","DOI":"10.1038\/mp.2008.47","volume":"13","author":"PWJ Burnet","year":"2008","unstructured":"Burnet PWJ, Eastwood SL, Bristow GC, Godlewska BR, Sikka P, Walker M, Harrison PJ (2008) d-amino acid oxidase activity and expression are increased in schizophrenia. Mol Psychiatry 13(7):658\u2013660","journal-title":"Mol Psychiatry"},{"issue":"1","key":"97_CR3","doi-asserted-by":"publisher","first-page":"30","DOI":"10.1007\/s00213-005-2199-1","volume":"179","author":"MJ Millan","year":"2005","unstructured":"Millan MJ (2005) N-methyl-d-aspartate receptors as a target for improved antipsychotic agents: novel insights and clinical perspectives. Psychopharmacology 179(1):30\u201353","journal-title":"Psychopharmacology"},{"issue":"12","key":"97_CR4","doi-asserted-by":"publisher","first-page":"3357","DOI":"10.1021\/jm800200u","volume":"51","author":"D Ferraris","year":"2008","unstructured":"Ferraris D, Duvall B, Ko Y-S, Thomas AG, Rojas C, Majer P, Hashimoto K, Tsukamoto T (2008) Synthesis and biological evaluation of d-amino acid oxidase inhibitors. J Med Chem 51(12):3357\u20133359","journal-title":"J Med Chem"},{"issue":"2","key":"97_CR5","doi-asserted-by":"publisher","first-page":"152","DOI":"10.1007\/s12035-007-0038-6","volume":"36","author":"H Wolosker","year":"2007","unstructured":"Wolosker H (2007) NMDA receptor regulation by d-serine: new findings and perspectives. Mol Neurobiol 36(2):152\u2013164","journal-title":"Mol Neurobiol"},{"issue":"3","key":"97_CR6","doi-asserted-by":"publisher","first-page":"200","DOI":"10.1016\/j.euroneuro.2007.06.006","volume":"18","author":"T Adage","year":"2008","unstructured":"Adage T, Trillat A-C, Quattropani A, Perrin D, Cavarec L, Shaw J, Guerassimenko O, Giachetti C, Gr\u00e9co B, Chumakov I, Halazy S, Roach A, Zaratin P (2008) In vitro and in vivo pharmacological profile of AS057278, a selective d-amino acid oxidase inhibitor with potential anti-psychotic properties. Eur Neuropsychopharmacol 18(3):200\u2013214","journal-title":"Eur Neuropsychopharmacol"},{"issue":"10","key":"97_CR7","doi-asserted-by":"publisher","first-page":"4808","DOI":"10.1016\/j.ejmech.2011.04.023","volume":"46","author":"JHM Lange","year":"2011","unstructured":"Lange JHM, Venhorst J, van Dongen MJP, Frankena J, Bassissi F, de Bruin NMWJ., den Besten C, de Beer SBA, Oostenbrink C, Markova N, Kruse CG (2011) Biophysical and physicochemical methods differentiate highly ligand-efficient human d-amino acid oxidase inhibitors. Eur J Med Chem 46(10):4808\u20134819","journal-title":"Eur J Med Chem"},{"issue":"11","key":"97_CR8","doi-asserted-by":"publisher","first-page":"3386","DOI":"10.1016\/j.bmcl.2008.04.020","volume":"18","author":"T Sparey","year":"2008","unstructured":"Sparey T, Abeywickrema P, Almond S, Brandon N, Byrne N, Campbell A, Hutson PH, Jacobson M, Jones B, Munshi S, Pascarella D, Pike A, Prasad GS, Sachs N, Sakatis M, Sardana V, Venkatraman S, Young MB (2008) The discovery of fused pyrrole carboxylic acids as novel, potent d-amino acid oxidase (DAO) inhibitors. Bioorg Med Chem Lett 18(11):3386\u20133391","journal-title":"Bioorg Med Chem Lett"},{"issue":"3","key":"97_CR9","doi-asserted-by":"publisher","first-page":"921","DOI":"10.1124\/jpet.108.147884","volume":"328","author":"SM Smith","year":"2009","unstructured":"Smith SM, Uslaner JM, Yao L, Mullins CM, Surles NO, Huszar SL, McNaughton CH, Pascarella DM, Kandebo M, Hinchliffe RM, Sparey T, Brandon NJ, Jones B, Venkatraman S, Young MB, Sachs N, Jacobson MA, Hutson PH (2009) The behavioral and neurochemical effects of a novel d-amino acid oxidase inhibitor compound 8 [4H-Thieno [3,2-B]pyrrole-5-carboxylic acid] and d-serine. J Pharmacol Exp Ther 328(3):921\u2013930","journal-title":"J Pharmacol Exp Ther"},{"issue":"11","key":"97_CR10","doi-asserted-by":"publisher","first-page":"3576","DOI":"10.1021\/jm900128w","volume":"52","author":"AJ Duplantier","year":"2009","unstructured":"Duplantier AJ, Becker SL, Bohanon MJ, Borzilleri KA, Chrunyk BA, Downs JT, Hu LY, El-Kattan A, James LC, Liu S, Lu J, Maklad N, Mansour MN, Mente S, Piotrowski MA, Sakya SM, Sheehan S, Steyn SJ, Strick CA, Williams VA, Zhang L (2009) Discovery, SAR, and pharmacokinetics of a novel 3-Hydroxyquinolin-2(1H)-one series of potent d-amino acid oxidase (DAAO) inhibitors. J Med Chem 52(11):3576\u20133585","journal-title":"J Med Chem"},{"issue":"10","key":"97_CR11","doi-asserted-by":"publisher","first-page":"839","DOI":"10.1021\/ml300212a","volume":"3","author":"JF Berry","year":"2012","unstructured":"Berry JF, Ferraris DV, Duvall B, Hin N, Rais R, Alt J, Thomas AG, Rojas C, Hashimoto K, Slusher BS, Tsukamoto T (2012) Synthesis and SAR of 1-hydroxy-1H-Benzo[d]imidazol-2(3H)-ones as inhibitors of d-amino acid oxidase. ACS Med Chem Lett 3(10):839\u2013843","journal-title":"ACS Med Chem Lett"},{"issue":"9","key":"97_CR12","doi-asserted-by":"publisher","first-page":"3710","DOI":"10.1021\/jm4002583","volume":"56","author":"SC Hopkins","year":"2013","unstructured":"Hopkins SC, Heffernan MLR, Saraswat LD, Bowen CA, Melnick L, Hardy LW, Orsini MA, Allen MS, Koch P, Spear KL, Foglesong RJ, Soukri M, Chytil M, Fang QK, Jones SW, Varney MA, Panatier A, Oliet SHR, Pollegioni L, Piubelli L, Molla G, Nardini M, Large TH (2013) Structural, kinetic, and pharmacodynamic mechanisms of d-amino acid oxidase inhibition by small molecules. J Med Chem 56(9):3710\u20133724","journal-title":"J Med Chem"},{"key":"97_CR13","doi-asserted-by":"publisher","first-page":"38","DOI":"10.1016\/j.sbi.2016.10.007","volume":"43","author":"R Abel","year":"2017","unstructured":"Abel R, Mondal S, Masse C, Greenwood J, Harriman G, Ashwell MA, Bhat S, Wester R, Frye L, Kapeller R, Friesner RA (2017) Accelerating drug discovery through tight integration of expert molecular design and predictive scoring. Curr Opin Struct Biol 43:38\u201344","journal-title":"Curr Opin Struct Biol"},{"issue":"7","key":"97_CR14","doi-asserted-by":"publisher","first-page":"2695","DOI":"10.1021\/ja512751q","volume":"137","author":"L Wang","year":"2015","unstructured":"Wang L, Wu Y, Deng Y, Kim B, Pierce L, Krilov G, Lupyan D, Robinson S, Dahlgren MK, Greenwood J, Romero DL, Masse C, Knight JL, Steinbrecher T, Beuming T, Damm W, Harder E, Sherman W, Brewer M, Wester R, Murcko M, Frye L, Farid R, Lin T, Mobley DL, Jorgensen WL, Berne BJ, Friesner RA, Abel R (2015) Accurate and reliable prediction of relative ligand binding potency in prospective drug discovery by way of a modern free-energy calculation protocol and force field. J Am Chem Soc 137(7):2695\u20132703","journal-title":"J Am Chem Soc"},{"issue":"1","key":"97_CR15","doi-asserted-by":"publisher","first-page":"281","DOI":"10.1021\/acs.jctc.5b00864","volume":"12","author":"E Harder","year":"2016","unstructured":"Harder E, Damm W, Maple J, Wu C, Reboul M, Xiang JY, Wang L, Lupyan D, Dahlgren MK, Knight JL, Kaus JW, Cerutti DS, Krilov G, Jorgensen WL, Abel R, Friesner RA (2016) OPLS3: a force field providing broad coverage of drug-like small molecules and proteins. J Chem Theory Comput 12(1):281\u2013296","journal-title":"J Chem Theory Comput"},{"issue":"6","key":"97_CR16","doi-asserted-by":"publisher","first-page":"2485","DOI":"10.1021\/acs.jmedchem.6b01881","volume":"60","author":"B Kuhn","year":"2017","unstructured":"Kuhn B, Tich\u00fd M, Wang L, Robinson S, Martin RE, Kuglstatter A, Benz J, Giroud M, Schirmeister T, Abel R, Diederich F, Hert J (2017) Prospective evaluation of free energy calculations for the prioritization of cathepsin L inhibitors. J Med Chem 60(6):2485\u20132497","journal-title":"J Med Chem"},{"issue":"11","key":"97_CR17","doi-asserted-by":"publisher","first-page":"2411","DOI":"10.1021\/acs.jcim.5b00538","volume":"55","author":"TB Steinbrecher","year":"2015","unstructured":"Steinbrecher TB, Dahlgren M, Cappel D, Lin T, Wang L, Krilov G, Abel R, Friesner R, Sherman W (2015) Accurate binding free energy predictions in fragment optimization. J Chem Inf Model 55(11):2411\u20132420","journal-title":"J Chem Inf Model"},{"key":"97_CR18","unstructured":"Fang QK, Hopkins S, Jones S (2005) Espacenet - Bibliographic Data"},{"key":"97_CR19","unstructured":"FEP+, Schr\u00f6dinger LLC (2017) New York, NY"},{"key":"97_CR20","unstructured":"Schr\u00f6dinger Suite 2017\u20132 Protein Preparation Wizard, Epik, Prime, Schr\u00f6dinger LLC (2017) New York, NY"},{"key":"97_CR21","doi-asserted-by":"crossref","unstructured":"Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE (2000) The Protein Data Bank Nucleic Acids Research, 28(1):235\u2013242","DOI":"10.1093\/nar\/28.1.235"},{"key":"97_CR22","unstructured":"Glide, Schr\u00f6dinger LLC (2017) New York, NY"},{"issue":"2","key":"97_CR23","doi-asserted-by":"publisher","first-page":"95","DOI":"10.1002\/jcc.23444","volume":"35","author":"AW G\u00f6tz","year":"2014","unstructured":"G\u00f6tz AW, Clark MA, Walker RC (2014) An extensible interface for QM\/MM molecular dynamics simulations with AMBER. J Comput Chem 35(2):95\u2013108","journal-title":"J Comput Chem"},{"issue":"11","key":"97_CR24","doi-asserted-by":"publisher","first-page":"132","DOI":"10.1007\/s00214-015-1734-3","volume":"134","author":"B H\u00e9gely","year":"2015","unstructured":"H\u00e9gely B, Bog\u00e1r F, Ferenczy GG, K\u00e1llay M (2015) A QM\/MM program using frozen localized orbitals and the Huzinaga equation. Theor Chem Acc 134(11):132","journal-title":"Theor Chem Acc"},{"issue":"3","key":"97_CR25","doi-asserted-by":"publisher","first-page":"341","DOI":"10.1248\/jhs.56.341","volume":"56","author":"Z Song","year":"2010","unstructured":"Song Z, Ogaya T, Ishii K, Ichiba H, Iizuka H, Fukushima T (2010) Utilization of kynurenic acid produced from d-Kynurenine in an in vitro assay of d-amino acid oxidase activity. J Heal Sci 56(3):341\u2013346","journal-title":"J Heal Sci"},{"issue":"4","key":"97_CR26","first-page":"263","volume":"70c","author":"HH Ku","year":"1966","unstructured":"Ku HH (1966) Notes on the use of propagation of error formulas. J Res 70c(4):263\u2013273","journal-title":"J Res"},{"issue":"2","key":"97_CR27","doi-asserted-by":"publisher","first-page":"1282","DOI":"10.1021\/ct300911a","volume":"9","author":"L Wang","year":"2013","unstructured":"Wang L, Deng Y, Knight JL, Wu Y, Kim B, Sherman W, Shelley JC, Lin T, Abel R (2013) Modeling local structural rearrangements using FEP\/REST: application to relative binding affinity predictions of CDK2 inhibitors. J Chem Theory Comput 9(2):1282\u20131293","journal-title":"J Chem Theory Comput"},{"issue":"7\u20138","key":"97_CR28","doi-asserted-by":"publisher","first-page":"420","DOI":"10.1016\/j.drudis.2009.01.012","volume":"14","author":"SP Brown","year":"2009","unstructured":"Brown SP, Muchmore SW, Hajduk PJ (2009) Healthy skepticism: assessing realistic model performance. Drug Discov Today 14(7\u20138):420\u2013427","journal-title":"Drug Discov Today"},{"issue":"2","key":"97_CR29","doi-asserted-by":"publisher","first-page":"332","DOI":"10.1039\/C5MD00542F","volume":"7","author":"GG Ferenczy","year":"2016","unstructured":"Ferenczy GG, Keser\u0171 GM (2016) On the enthalpic preference of fragment binding. Med Chem Commun 7(2):332\u2013337","journal-title":"Med Chem Commun"},{"issue":"19\u201320","key":"97_CR30","doi-asserted-by":"publisher","first-page":"869","DOI":"10.1016\/j.drudis.2008.07.005","volume":"13","author":"E Freire","year":"2008","unstructured":"Freire E (2008) Do enthalpy and entropy distinguish first in class from best in class?. Drug Discovery Today 13(19\u201320):869\u2013874","journal-title":"Drug Discovery Today"},{"issue":"10","key":"97_CR31","doi-asserted-by":"publisher","first-page":"1285","DOI":"10.4155\/fmc.15.63","volume":"7","author":"GG Ferenczy","year":"2015","unstructured":"Ferenczy GG, Keser\u0171 GM (2015) The impact of binding thermodynamics on medicinal chemistry optimizations. Future Med Chem 7(10):1285\u20131303","journal-title":"Future Med Chem"}],"container-title":["Journal of Computer-Aided Molecular Design"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/link.springer.com\/article\/10.1007\/s10822-018-0097-y\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/link.springer.com\/content\/pdf\/10.1007\/s10822-018-0097-y.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/link.springer.com\/content\/pdf\/10.1007\/s10822-018-0097-y.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2019,10,9]],"date-time":"2019-10-09T06:16:36Z","timestamp":1570601796000},"score":1,"resource":{"primary":{"URL":"http:\/\/link.springer.com\/10.1007\/s10822-018-0097-y"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,1,15]]},"references-count":31,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2018,2]]}},"alternative-id":["97"],"URL":"https:\/\/doi.org\/10.1007\/s10822-018-0097-y","relation":{},"ISSN":["0920-654X","1573-4951"],"issn-type":[{"type":"print","value":"0920-654X"},{"type":"electronic","value":"1573-4951"}],"subject":[],"published":{"date-parts":[[2018,1,15]]},"assertion":[{"value":"4 October 2017","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"6 January 2018","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"15 January 2018","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}}]}}