Tautomer Database

Tautomer Database provides a curated collection of experimentally derived tautomeric structures to support analyses of tautomerism and studies of tautomeric equilibria.

Key Features:

• Comprehensive Data Collection: The database compiles 5,977 unique chemical structures extracted from 171 scientific publications covering 2,819 distinct tautomeric tuples (pairs, triples, and higher-order cases) and includes bibliographic references, structural identifiers (NCI/CADD FICTS, FICuS, uuuuu, Standard InChI), SMILES notation, and molecular weight.
• Types of Tautomerism: Entries are categorized by tautomerism type with prototropic tautomerism comprising 79%, ring–chain 13%, and valence 8% of cases.
• Experimental Conditions: The dataset records experimental context including 50 pure solvents, 9 solvent mixtures, and 26 spectroscopic or nonspectroscopic methods with 1H and 13C NMR as the most commonly used techniques.
• Tautomeric Transform Rules: The resource includes examples of 77 distinct tautomeric transform rules encoded as SMIRKS.

Scientific Applications:

• Chemical Equilibria Analysis: Supports quantitative and qualitative studies of tautomeric equilibria across documented solvents and methods.
• Drug Discovery: Provides experimentally observed tautomeric states to inform considerations of molecular flexibility and conformational variability in ligand design.
• Computational Chemistry: Supplies experimentally derived tautomer examples and transform rules for benchmarking and improving tautomer-prediction methods.

Methodology:

Entries contain bibliographic references and computational representations including structural identifiers (NCI/CADD FICTS, FICuS, uuuuu, Standard InChI), SMILES notation, molecular weights, and examples of 77 tautomeric transform rules encoded as SMIRKS.