Beyond Rotatable Bond Counts: Capturing 3D Conformational Flexibility in a Single Descriptor

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• 作者：Jerome G. P. Wicker ; Richard I. Cooper
• 刊名：Journal of Chemical Information and Modeling
• 出版年：2016
• 出版时间：December 27, 2016
• 年：2016
• 卷：56
• 期：12
• 页码：2347-2352
• 全文大小：384K
• ISSN：1549-960X

文摘

A new molecular descriptor, nConf₂₀, based on chemical connectivity, is presented which captures the accessible conformational space of a molecule. Currently the best available two-dimensional descriptors for quantifying the flexibility of a particular molecule are the rotatable bond count (RBC) and the Kier flexibility index. We present a descriptor which captures this information by sampling the conformational space of a molecule using the RDKit conformer generator. Flexibility has previously been identified as a key feature in determining whether a molecule is likely to crystallize or not. For this application, nConf₂₀ significantly outperforms previously reported single-variable classifiers and also assists rule-based analysis of black-box machine learning classification algorithms.