Journal
JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN
Volume 32, Issue 3, Pages 401-414Publisher
SPRINGER
DOI: 10.1007/s10822-018-0101-6
Keywords
QSPR; Support vector regression; Condensed graphs of reaction; Tautomerism
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Funding
- Russian Science Foundation [14-43-00024]
- IDEX UniStra program
- Russian Science Foundation [17-43-00003] Funding Source: Russian Science Foundation
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We report the first direct QSPR modeling of equilibrium constants of tautomeric transformations (logK (T) ) in different solvents and at different temperatures, which do not require intermediate assessment of acidity (basicity) constants for all tautomeric forms. The key step of the modeling consisted in the merging of two tautomers in one sole molecular graph (condensed reaction graph) which enables to compute molecular descriptors characterizing entire equilibrium. The support vector regression method was used to build the models. The training set consisted of 785 transformations belonging to 11 types of tautomeric reactions with equilibrium constants measured in different solvents and at different temperatures. The models obtained perform well both in cross-validation (Q(2) = 0.81 RMSE = 0.7 logK (T) units) and on two external test sets. Benchmarking studies demonstrate that our models outperform results obtained with DFT B3LYP/6-311 ++ G(d,p) and ChemAxon Tautomerizer applicable only in water at room temperature.
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