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Tautomer Database: A Comprehensive Resource for Tautomerism Analyses

  1. Author:
    Dhaked,Devendra Kumar
    Guasch, Laura
    Nicklaus,Marc

  2. Author Address

    NCI, Comp Aided Drug Design Grp, Chem Biol Lab, Ctr Canc Res, Frederick, MD 21702 USA.
    1. Year: 2020
    2. Date: Mar 23
  2. Journal: JOURNAL OF CHEMICAL INFORMATION AND MODELING
  3. AMER CHEMICAL SOC,
    1. 60
    2. Pages: 1090-1100
  5. Type of Article: Article
  6. ISSN: 1549-9596
  1. Abstract:

    We report a database of tautomeric structures that contains 2819 tautomeric tuples extracted from 171 publications. Each tautomeric entry has been annotated with experimental conditions reported in the respective publication, plus bibliographic details, structural identifiers (e.g., NCI/CADD identifiers FICTS, FICuS, uuuuu, and Standard InChI), and chemical information (e.g., SMILES, molecular weight). The majority of tautomeric tuples found were pairs; the remaining 10% were triples, quadruples, or quintuples, amounting to a total number of structures of 5977. The types of tautomerism were mainly prototropic tautomerism (79%), followed by ring-chain (13%) and valence tautomerism (8%). The experimental conditions reported in the publications included about 50 pure solvents and 9 solvent mixtures with 26 unique spectroscopic or nonspectroscopic methods. H-1 and C-13 NMR were the most frequently used methods. A total of 77 different tautomeric transform rules (SMIRKS) are covered by at least one example tuple in the database. This database is freely available as a spreadsheet at https://cactus.nci.nih.gov/download/tautomer/.

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External Sources

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  2. DOI: 10.1021/acs.jcim.9b01156
  3. PMID: 32027495
  4. View record in Web of Science®
  5. WOS: 000526390800006

Library Notes

  1. Fiscal Year: FY2019-2020
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