Cross-validation strategies in QSPR modelling of chemical reactions

Rakhimbekova, Assima; Akhmetshin, Tagir N.; Minibaeva, Guzel I. et al.

SAR and QSAR in environmental research, 2021, 32(3), 207-219

Permalink : https://hdl.handle.net/2115/84176

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アクセス権
open access
URI
https://hdl.handle.net/2115/84176
タイトル
Cross-validation strategies in QSPR modelling of chemical reactions
著者
Rakhimbekova, Assima ; Akhmetshin, Tagir N. ; Minibaeva, Guzel I. ; Nugmanov, Ramil I. ; Gimadiev, Timur R. ; Madzhidov, Timur I. ; Baskin, Igor I. ; Varnek, Alexandre
著者名
Rakhimbekova, Assima
著者名
Akhmetshin, Tagir N.
著者名
Minibaeva, Guzel I.
著者名
Nugmanov, Ramil I.
著者名
Gimadiev, Timur R.
著者名
Madzhidov, Timur I.
著者名
Baskin, Igor I.
著者名
Varnek, Alexandre
言語
英語
キーワード
Validation
QSPR
chemical reactions
rate constant prediction
reaction rate
structure-reactivity modelling
発行日
2021-02-19
出版者
Taylor & Francis
収録物名
SAR and QSAR in environmental research
巻(号)
32(3)
ページ
207-219
抄録
In this article, we consider cross-validation of the quantitative structure-property relationship models for reactions and show that the conventional k-fold cross-validation (CV) procedure gives an `optimistically' biased assessment of prediction performance. To address this issue, we suggest two strategies of model cross-validation, `transformation-out' CV, and `solvent-out' CV. Unlike the conventional k-fold cross-validation approach that does not consider the nature of objects, the proposed procedures provide an unbiased estimation of the predictive performance of the models for novel types of structural transformations in chemical reactions and reactions going under new conditions. Both the suggested strategies have been applied to predict the rate constants of bimolecular elimination and nucleophilic substitution reactions, and Diels-Alder cycloaddition. All suggested cross-validation methodologies and tutorial are implemented in the open-source software package CIMtools (https://github.com/cimm-kzn/CIMtools).
資源タイプ
学術雑誌論文
出版タイプ
Accepted Manuscript
権利情報
This is an Accepted Manuscript of an article published by Taylor & Francis in SAR and QSAR in Environmental Research on 19 Feb 2021, available online: http://www.tandfonline.com/10.1080/1062936X.2021.1883107
PISSN
1062-936X
関連情報 (isVersionOf)
出版社版DOI
https://doi.org/10.1080/1062936X.2021.1883107