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3D molecular fragment descriptors for structure–property modeling: predicting the free energies for the complexation between antipodal guests and β-cyclodextrinsстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 3 декабря 2017 г.
- Авторы: Solovev A., Solov'ev V.
- Журнал: JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
- Том: 89
- Номер: 1-2
- Год издания: 2017
- Первая страница: 167
- Последняя страница: 175
- DOI: 10.1007/s10847-017-0739-z
- Аннотация: We report new 3D fragment descriptors to model parameters and properties of stereoisomeric mol- ecules and conformers. New 3D fragment descriptors have been applied to discriminate between stereoisomers in pre- dictive QSPR modeling of the standard free energy (∆G°) for the 1:1 inclusion complexation of 76 chiral guests with β-cyclodextrin (β-CD) and 40 chiral guests with 6-amino- 6-deoxy-β-cyclodextrin (am-β-CD) in water at 298 K. The in-house software, mfSpace (Molecular Fragments Space), was used for QSPR modeling, generation and coding of the 3D fragment descriptors. The program implements the Sin- gular Value Decomposition for Multiple Linear Regression analysis as machine learning method. We used ensemble modeling techniques which include the generation of many individual models, the selection of the most relevant ones and followed by their joint application to test compounds, i.e., applying a consensus model for average predictions. The models based on 2D and 3D fragment descriptors provide the best predictions in external fivefold cross-validation: root mean squared error RMSE = 1.1 kJ/mol and determination coefficient R2det = 0.918 (β-CD), RMSE = 0.89 kJ/mol and R2det = 0.910 (am-β-CD).
- Добавил в систему: Соловьев Виталий Петрович