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Cross-validation strategies in QSPR modelling of chemical reactions
| Title: | Cross-validation strategies in QSPR modelling of chemical reactions |
| Authors: | Rakhimbekova, Assima Browse this author | | Akhmetshin, Tagir N. Browse this author | | Minibaeva, Guzel I. Browse this author | | Nugmanov, Ramil I. Browse this author | | Gimadiev, Timur R. Browse this author | | Madzhidov, Timur I. Browse this author | | Baskin, Igor I. Browse this author | | Varnek, Alexandre Browse this author |
| Keywords: | Validation | | QSPR | | chemical reactions | | rate constant prediction | | reaction rate | | structure-reactivity modelling |
| Issue Date: | 19-Feb-2021 |
| Publisher: | Taylor & Francis |
| Journal Title: | SAR and QSAR in environmental research |
| Volume: | 32 |
| Issue: | 3 |
| Start Page: | 207 |
| End Page: | 219 |
| Publisher DOI: | 10.1080/1062936X.2021.1883107 |
| Abstract: | 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). |
| Rights: | 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 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/84176 |
| Appears in Collections: | 化学反応創成研究拠点：ICReDD (Institute for Chemical Reaction Design and Discovery : ICReDD) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: Alexandre Varnek
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