QSAR models based on quantum topological molecular similarity

P. L A Popelier, P. J. Smith

    Research output: Contribution to journalArticlepeer-review


    A new method called quantum topological molecular similarity (QTMS) was fairly recently proposed [J. Chem. Inf. Comp. Sc., 41, 2001, 764] to construct a variety of medicinal, ecological and physical organic QSAR/QSPRs. QTMS method uses quantum chemical topology (QCT) to define electronic descriptors drawn from modern ab initio wave functions of geometry-optimised molecules. It was shown that the current abundance of computing power can be utilised to inject realistic descriptors into QSAR/QSPRs. In this article we study seven datasets of medicinal interest [1]: the dissociation constants (pKa) for a set of substituted imidazolines [2], the pKa of imidazoles [3], the ability of a set of indole derivatives to displace [3H] flunitrazepam from binding to bovine cortical membranes [4], the influenza inhibition constants for a set of benzimidazoles [5], the interaction constants for a set of amides and the enzyme liver alcohol dehydrogenase [6], the natriuretic activity of sulphonamide carbonic anhydrase inhibitors and [7] the toxicity of a series of benzyl alcohols. A partial least square analysis in conjunction with a genetic algorithm delivered excellent models. They are also able to highlight the active site, of the ligand or the molecule whose structure determines the activity. The advantages and limitations of QTMS are discussed. © 2006 Elsevier SAS. All rights reserved.
    Original languageEnglish
    Pages (from-to)862-873
    Number of pages11
    JournalEuropean Journal of Medicinal Chemistry
    Issue number7
    Publication statusPublished - Jul 2006


    • Ab initio
    • Atoms in molecules
    • Electron density
    • pKa
    • PLS
    • QSAR
    • QSPR
    • Quantum chemical topology
    • Topology


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