3D molecular fragment descriptors for structure–property modeling: predicting the free energies for the complexation between antipodal guests and β-cyclodextrinsстатья
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Дата последнего поиска статьи во внешних источниках: 3 декабря 2017 г.
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).