Abstract：
: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 "Chemistry Business Rules", sets of predefined rules that describe the "house style" 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.
journal_name
J Chem Inf Modeljournal_title
Journal of chemical information and modelingauthors
Baker CM,Kidley NJ,Papachristos K,Hotson M,Carson R,Gravestock D,Pouliot M,Harrison J,Dowling Adoi
10.1021/acs.jcim.0c00232subject
Has Abstractpub_date
2020-08-24 00:00:00pages
3781-3791issue
8eissn
1549-9596issn
1549-960Xjournal_volume
60pub_type
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