Tautomer Standardization in Chemical Databases: Deriving Business Rules from Quantum Chemistry.

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ID: 108985
2020
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Abstract
Databases of small, potentially-bioactive molecules are ubiquitous across 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 pre-defined 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.
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baker2020tautomerjournal Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Baker, Christopher M;Kidley, Nathan J;Papachristos, Konstantinos;Hotson, Matthew;Carson, Rob;Gravestock, David;Pouliot, Martin;Harrison, Jim;Dowling, Alan J;
Journal Journal of chemical information and modeling
Year 2020
DOI
10.1021/acs.jcim.0c00232
URL
Keywords
quality indicators Critical illness end-of-life care icu care medical-record reviews

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