Golbraikh A, Bonchev D, Tropsha A
Division of Medicinal Chemistry and Natural Products, School of Pharmacy, University of North Carolina at Chapel Hill, 27599-7360, USA.
J Chem Inf Comput Sci. 2001 Jan-Feb;41(1):147-58. doi: 10.1021/ci000082a.
Several series of novel chirality descriptors of chemical organic molecules have been introduced. The descriptors have been developed on the basis of conventional topological descriptors of molecular graphs. They include modified molecular connectivity indices, Zagreb group indices, extended connectivity, overall connectivity, and topological charge indices. These modified descriptors make use of an additional term called chirality correction, which is added to the vertex degrees of asymmetric atoms in a molecular graph. Chirality descriptors can be real or complex numbers. Advantages and drawbacks of different series of chirality descriptors are discussed. These descriptors circumvent the inability of conventional topological indices to distinguish chiral or enantiomeric isomers, which so far has been the major drawback of 2D descriptors as compared to true 3D descriptors (e.g., shape, molecular fields) of molecular structure. These novel chirality descriptors have been implemented in a quantitative structure-activity releationship (QSAR) study of a set of ecdysteroids with a high content of chiral and enantiomeric compounds using the k nearest neighbor QSAR method (kNN) recently developed in this laboratory. We show that the results of this study compare favorably with those obtained with the comparative molecular field analysis (CoMFA) applied to the same dataset. The novel chirality descriptors of molecular structure should find their applications in QSAR studies and related investigations of molecular sdatasets.
已经引入了几个系列的新型化学有机分子手性描述符。这些描述符是在分子图的传统拓扑描述符的基础上开发的。它们包括修改后的分子连接性指数、 Zagreb 群指数、扩展连接性、整体连接性和拓扑电荷指数。这些修改后的描述符利用了一个称为手性校正的附加项，该项被添加到分子图中不对称原子的顶点度数上。手性描述符可以是实数或复数。讨论了不同系列手性描述符的优缺点。这些描述符克服了传统拓扑指数无法区分手性或对映体异构体的问题，与分子结构的真实三维描述符（例如形状、分子场）相比，这一直是二维描述符的主要缺点。这些新型手性描述符已在使用本实验室最近开发的 k 最近邻 QSAR 方法（kNN）对一组含有高含量手性和对映体化合物的蜕皮甾类进行的定量构效关系（QSAR）研究中得到应用。我们表明，该研究的结果与应用于同一数据集的比较分子场分析（CoMFA）所获得的结果相比具有优势。分子结构的新型手性描述符应在 QSAR 研究和分子数据集的相关研究中找到其应用。
