Tautomer Database: A Comprehensive Resource for Tautomerism Analyses
Devendra K. Dhaked, Laura Guasch, and Marc C. Nicklaus
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. 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 freely available as a spreadsheet at https://cactus.nci.nih.gov/download/tautomer/.
|Author(s)||Devendra K. Dhaked, Laura Guasch, Marc C. Nicklaus|
|License||Copyright © 2020 American Chemical Society, HHS Public Access through PubMed Central|
|Date Published||March 10, 2020|
|Content Tags||Cheminformatics, Classroom Material, Content type, Extended Tautomers, Organic, Publication|