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Toward a Comprehensive Treatment of Tautomerism in Chemoinformatics Including in InChI V2

  1. Author:
    Dhaked,Devendra Kumar
    Ihlenfeldt, Wolf-Dietrich
    Patel,Hitesh
    Delannee,Victorien
    Nicklaus,Marc

  2. Author Address

    NCI, Comp Aided Drug Design Grp, Chem Biol Lab, Ctr Canc Res,NIH, Frederick, MD 21702 USA.Xemistry GmbH, D-61479 Glashutten, Germany.
    1. Year: 2020
    2. Date: Mar 23
  2. Journal: JOURNAL OF CHEMICAL INFORMATION AND MODELING
  3. AMER CHEMICAL SOC,
    1. 60
    2. 3
    3. Pages: 1253-1275
  5. Type of Article: Article
  6. ISSN: 1549-9596
  1. Abstract:

    We have collected 86 different transforms of tautomeric interconversions. Out of those, 54 are for prototropic (non-ring-chain) tautomerism, 21 for ring-chain tautomerism, and 11 for valence tautomerism. The majority of these rules have been extracted from experimental literature. Twenty rules, covering the most well-known types of tautomerism such as keto-enol tautomerism, were taken from the default handling of tautomerism by the chemoinformatics toolkit CACTVS. The rules were analyzed against nine differerent databases totaling over 400 million (non-unique) structures as to their occurrence rates, mutual overlap in coverage, and recapitulation of the rules' enumerated tautomer sets by InChI V.1.05, both in InChI's Standard and a Nonstandard version with the increased tautomer-handling options 15T and KET turned on. These results and the background of this study are discussed in the context of the IUPAC InChI Project tasked with the redesign of handling of tautomerism for an InChI version 2. Applying the rules presented in this paper would approximately triple the number of compounds in typical small-molecule databases that would be affected by tautomeric interconversion by InChI V2. A web tool has been created to test these rules at https://cactus.nci.nih.gov/tautomerizer.

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External Sources

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  2. DOI: 10.1021/acs.jcim.9b01080
  3. PMID: 32043883
  4. View record in Web of Science®
  5. WOS: 000526390800021

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  1. Fiscal Year: FY2019-2020
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