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A chemometric study on the analgesic activity of cannabinoid compounds using SDA, KNN and SIMCA methods

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Abstract

The supervised pattern recognition methods K-Nearest Neighbors (KNN), stepwise discriminant analysis (SDA), and soft independent modelling of class analogy (SIMCA) were employed in this work with the aim to investigate the relationship between the molecular structure of 27 cannabinoid compounds and their analgesic activity. Previous analyses using two unsupervised pattern recognition methods (PCA—principal component analysis and HCA—hierarchical cluster analysis) were performed and five descriptors were selected as the most relevants for the analgesic activity of the compounds studied: R 3 (charge density on substituent at position C3), Q 1 (charge on atom C1), A (surface area), log P (logarithm of the partition coefficient) and MR (molecular refractivity). The supervised pattern recognition methods (SDA, KNN, and SIMCA) were employed in order to construct a reliable model that can be able to predict the analgesic activity of new cannabinoid compounds and to validate our previous study. The results obtained using the SDA, KNN, and SIMCA methods agree perfectly with our previous model. Comparing the SDA, KNN, and SIMCA results with the PCA and HCA ones we could notice that all multivariate statistical methods classified the cannabinoid compounds studied in three groups exactly in the same way: active, moderately active, and inactive.

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Acknowledgments

The authors would like to thank FAPESP and CNPq (Brazilian agencies) for the financial support.

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Authors and Affiliations

  1. Faculdade de Educação, Departamento de Metodologia do Ensino e Educação Comparada, Universidade de São Paulo, Av. da Universidade 308, bloco B, sala 1, 05508-900, São Paulo, SP, Brazil

    A. Arroio

  2. Instituto de Química de São Carlos, Universidade de São Paulo, C. P. 780, 13560-970, São Carlos, SP, Brazil

    E. F. Lima & A. B. F. da Silva

  3. Escola de Artes, Ciências e Humanidades, Universidade de São Paulo, Av. Arlindo Bettio, 1000, 03828-000, São Paulo, SP, Brazil

    K. M. Honório

  4. Universidade Federal do ABC (UFABC), Rua Santa Adélia, 166, Bairro Bangu, 09210-170, Santo André, SP, Brazil

    K. M. Honório

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  1. A. Arroio
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  2. E. F. Lima
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  3. K. M. Honório
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  4. A. B. F. da Silva
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Corresponding author

Correspondence to A. B. F. da Silva.

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Arroio, A., Lima, E.F., Honório, K.M. et al. A chemometric study on the analgesic activity of cannabinoid compounds using SDA, KNN and SIMCA methods. Struct Chem 20, 577–585 (2009). https://doi.org/10.1007/s11224-009-9437-9

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  • DOI: https://doi.org/10.1007/s11224-009-9437-9

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