Advanced exact structure searching in large databases of chemical compounds
Advanced exact structure searching in large databases of chemical compounds
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DOI：
10.1021/ci025582d
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发表时间：
2003-05-01
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影响因子：
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通讯作者：
Savchuk, NP
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作者：
Trepalin, SV;Skorenko, AV;Savchuk, NP
在大型公司或市售化合物数据库中有效识别互变异构化合物形式是一项困难且劳动密集的任务。我们的数据表明，高达0.5%的商业上可获得的化合物生物筛选集合包含互变异构体。虽然在大型注册数据库，如贝尔斯坦和CAS，互变异构体的发现在一个自动化的方式使用高性能的计算技术，他们的实时识别在非注册公司数据库，作为一项规则，仍然存在问题。我们已经开发了一个有效的算法，互变异构体搜索的基础上专有的化学信息学平台。该算法将化合物简化为规范结构。这一特点使得快速，自动化的计算机搜索大多数已知的互变异构体的转换，发生在数据库中的有机化合物。该方法的另一个有用的扩展涉及有效地搜索含有离子键和半极性键的不同形式的化合物的能力。计算是在标准个人计算机上的Windows环境中进行的，这是一个非常有用的功能。所提出的方法的实际应用说明了几个例子，成功回收的互变异构体和不同形式的离子化合物从真实的商业上可用的nonregistry数据库。
Efficient recognition of tautomeric compound forms in large corporate or commercially available compound databases is a difficult and labor intensive task. Our data indicate that up to 0.5% of commercially available compound collections for bioscreening contain tautomers. Though in the large registry databases, such as Beilstein and CAS, the tautomers are found in an automated fashion using high-performance computational technologies, their real-time recognition in the nonregistry corporate databases, as a rule, remains problematic. We have developed an effective algorithm for tautomer searching based on the proprietary chemoinformatics platform. This algorithm reduces the compound to a canonical structure. This feature enables rapid, automated computer searching of most of the known tautomeric transformations that occur in databases of organic compounds. Another useful extension of this methodology is related to the ability to effectively search for different forms of compounds that contain ionic and semipolar bonds. The computations are performed in the Windows environment on a standard personal computer, a very useful feature. The practical application of the proposed methodology is illustrated by several examples of successful recovery of tautomers and different forms of ionic compounds from real commercially available nonregistry databases.