Stereo Signature Molecular Descriptor

We present an algorithm to compute molecular graph descriptors considering the stereochemistry of the molecular structure based on our previously introduced signature molecular descriptor. The algorithm can generate two types of descriptors, one which is compliant with the Cahn–Ingold–Prelog priority rules, including complex stereochemistry structures such as fullerenes, and a computationally efficient one based on our previous definition of a directed acyclic graph that is augmented to a chiral molecular graph. The performance of the algorithm in terms of speed as a canonicalizer as well as in modeling and predicting bioactivity is evaluated, showing an overall better performance than other molecular descriptors, which is particularly relevant in modeling stereoselective biochemical reactions. The complete source code of the stereo signature molecular descriptor is available for download under an open-source license at http://molsig.sourceforge.net.本研究基于此前提出的签名分子描述符（signature molecular descriptor），提出一种可计算分子图描述符的算法，该算法充分考虑分子结构的立体化学特性。该算法可生成两类描述符：一类符合Cahn-Ingold-Prelog（Cahn–Ingold–Prelog）优先级规则，能够处理包括富勒烯在内的复杂立体化学结构；另一类基于此前定义的有向无环图（directed acyclic graph）扩展至手性分子图的形式，具备更优的计算效率。本研究评估了该算法作为规范化工具的运行速度，以及其在生物活性建模与预测任务中的性能，结果显示其整体表现优于其他分子描述符，这一点在立体选择性生化反应的建模研究中尤为关键。该立体签名分子描述符的完整源代码可在http://molsig.sourceforge.net以开源许可协议的形式获取下载。