How Does the Methodology of 3D Structure Preparation Influence the Quality of pK(a) Prediction?

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14740%2F15%3A00082988" target="_blank" >RIV/00216224:14740/15:00082988 - isvavai.cz</a>
Result on the web
<a href="http://pubs.acs.org/doi/pdf/10.1021/ci500758w" target="_blank" >http://pubs.acs.org/doi/pdf/10.1021/ci500758w</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/ci500758w" target="_blank" >10.1021/ci500758w</a>

Result language
angličtina
Original language name
How Does the Methodology of 3D Structure Preparation Influence the Quality of pK(a) Prediction?
Original language description
The acid dissociation constant is an important molecular property, and it can be successfully predicted by Quantitative Structure-Property Relationship (QSPR) models, even for in silico designed molecules. We analyzed how the methodology of in silico 3Dstructure preparation influences the quality of QSPR models. Specifically, we evaluated and compared QSPR models based on six different 3D structure sources (DTP NCI, Pubchem, Balloon, Frog2, OpenBabel, and RDKit) combined with four different types of optimization. These analyses were performed for three classes of molecules (phenols, carboxylic acids, anilines), and the QSPR model descriptors were quantum mechanical (QM) and empirical partial atomic charges. Specifically, we developed 516 QSPR models and afterward systematically analyzed the influence of the 3D structure source and other factors on their quality. Our results confirmed that QSPR models based on partial atomic charges are able to predict pK(a) with high accuracy.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CE - Biochemistry
OECD FORD branch
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Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2015
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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