Enhancing Carbon Acid pKa Prediction by Augmentation of Sparse Experimental Datasets with Accurate AIBL (QM) Derived Values.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Jeffrey PlantePaul Popelier

Abstract

The prediction of the aqueous pKa of carbon acids by Quantitative Structure Property Relationship or cheminformatics-based methods is a rather arduous problem. Primarily, there are insufficient high-quality experimental data points measured in homogeneous conditions to allow for a good global model to be generated. In our computationally efficient pKa prediction method, we generate an atom-type feature vector, called a distance spectrum, from the assigned ionisation atom, and learn coefficients for those atom-types that show the impact each atom-type has on the pKa of the ionisable centre. In the current work, we augment our dataset with pKa values from a series of high performing local models derived from the Ab Initio Bond Lengths method (AIBL). We find that, in distilling the knowledge available from multiple models into one general model, the prediction error for an external test set is reduced compared to that using literature experimental data alone.

References

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Software Mentioned

Simulations Plus
JAMA
RDKit
Lhasa
AIBL
GAUSSIAN09
inDomain
Zeneth
Lhasa pK
Reaxys

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