{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T11:28:26Z","timestamp":1787052506989,"version":"3.56.0"},"reference-count":84,"publisher":"American Chemical Society (ACS)","issue":"8","license":[{"start":{"date-parts":[[2020,7,9]],"date-time":"2020-07-09T00:00:00Z","timestamp":1594252800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2020,7,9]],"date-time":"2020-07-09T00:00:00Z","timestamp":1594252800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2020,7,9]],"date-time":"2020-07-09T00:00:00Z","timestamp":1594252800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,8,24]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Databases of small, potentially bioactive molecules are ubiquitous across the industry and academia. Designed such that each unique compound should appear only once, the multiplicity of ways in which many compounds can be represented means that these databases require methods for standardizing the representation of chemistry. This is commonly achieved through the use of \u201cChemistry Business Rules\u201d, sets of predefined rules that describe the \u201chouse style\u201d of the database in question. At Syngenta, the historical approach to the design of chemistry business rules has been to focus on consistency of representation, with chemical relevance given secondary consideration. In this work, we overturn that convention. Through the use of quantum chemistry calculations, we define a set of chemistry business rules for tautomer standardization that reproduces gas-phase energetic preferences. We go on to show that, compared to our historic approach, this method yields tautomers that are in better agreement with those observed experimentally in condensed phases and that are better suited for use in predictive models.<\/jats:p>","DOI":"10.1021\/acs.jcim.0c00232","type":"journal-article","created":{"date-parts":[[2020,7,9]],"date-time":"2020-07-09T12:17:46Z","timestamp":1594297066000},"page":"3781-3791","source":"Crossref","is-referenced-by-count":8,"title":["Tautomer Standardization in Chemical Databases: Deriving\nBusiness Rules from Quantum Chemistry"],"prefix":"10.1021","volume":"60","author":[{"given":"Christopher M.","family":"Baker","sequence":"first","affiliation":[{"name":"Syngenta, Jealott\u2019s Hill International Research Centre , , ,","place":["Bracknell, Berkshire, U.K., RG42 6EY"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nathan\nJ.","family":"Kidley","sequence":"additional","affiliation":[{"name":"Syngenta, Jealott\u2019s Hill International Research Centre , , ,","place":["Bracknell, Berkshire, U.K., RG42 6EY"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Konstantinos","family":"Papachristos","sequence":"additional","affiliation":[{"name":"Syngenta, Jealott\u2019s Hill International Research Centre , , ,","place":["Bracknell, Berkshire, U.K., RG42 6EY"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthew","family":"Hotson","sequence":"additional","affiliation":[{"name":"Syngenta, Jealott\u2019s Hill International Research Centre , , ,","place":["Bracknell, Berkshire, U.K., RG42 6EY"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rob","family":"Carson","sequence":"additional","affiliation":[{"name":"Syngenta, Jealott\u2019s Hill International Research Centre , , ,","place":["Bracknell, Berkshire, U.K., RG42 6EY"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Gravestock","sequence":"additional","affiliation":[{"name":"Syngenta, Jealott\u2019s Hill International Research Centre , , ,","place":["Bracknell, Berkshire, U.K., RG42 6EY"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Pouliot","sequence":"additional","affiliation":[{"name":"Syngenta Crop Protection , , ,","place":["Schaffhauserstrasse, Stein, Switzerland, CH-4332"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jim","family":"Harrison","sequence":"additional","affiliation":[{"name":"Datacraft Technologies , 110 Parkwood Place , , ,","place":["Anstead, QLD, Australia, 4070"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alan","family":"Dowling","sequence":"additional","affiliation":[{"name":"Syngenta, Jealott\u2019s Hill International Research Centre , , ,","place":["Bracknell, Berkshire, U.K., RG42 6EY"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,7,9]]},"reference":[{"key":"2026081805095455100_cit1","doi-asserted-by":"publisher","first-page":"2149","DOI":"10.1021\/acs.jcim.6b00338","article-title":"Experimental and Chemoinformatics\nStudy of Tautomerism in a Database of Commercially Available Screening\nSamples","volume":"56","author":"Guasch","year":"2016","journal-title":"J. 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