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Tautomer Database: A Comprehensive Resource for Tautomerism Analyses

preprint
submitted on 22.11.2019 and posted on 29.11.2019 by Devendra K. Dhaked, Laura Guasch, Marc Nicklaus

We report a database of tautomeric structures that contains 2,819 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 5,977. 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 non-spectroscopic methods. 1H and 13C 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 available as a spreadsheet for free download from https://cactus.nci.nih.gov/download/tautomer/.

Funding

NATIONAL INSTITUTES OF HEALTH (NIH)

United States Department of Health and Human Services

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History

Email Address of Submitting Author

mn1ahelix@gmail.com

Institution

National Cancer Institute, NIH

Country

United States

ORCID For Submitting Author

0000-0002-4775-7030

Declaration of Conflict of Interest

The authors declare no conflict of interest.

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in Journal of Chemical Information and Modeling

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