title: Artificial neural networks and the study of the psychoactivity of cannabinoid compounds.
abstract: Cannabinoid compounds have widely been employed because of its medicinal and psychotropic properties. These compounds are isolated from Cannabis sativa (or marijuana) and are used in several medical treatments, such as glaucoma, nausea associated to chemotherapy, pain and many other situations. More recently, its use as appetite stimulant has been indicated in patients with cachexia or AIDS. In this work, the influence of several molecular descriptors on the psychoactivity of 50 cannabinoid compounds is analyzed aiming one obtain a model able to predict the psychoactivity of new cannabinoids. For this purpose, initially, the selection of descriptors was carried out using the Fisher's weight, the correlation matrix among the calculated variables and principal component analysis. From these analyses, the following descriptors have been considered more relevant: E(LUMO) (energy of the lowest unoccupied molecular orbital), Log P (logarithm of the partition coefficient), VC4 (volume of the substituent at the C4 position) and LP1 (Lovasz-Pelikan index, a molecular branching index). To follow, two neural network models were used to construct a more adequate model for classifying new cannabinoid compounds. The first model employed was multi-layer perceptrons, with algorithm back-propagation, and the second model used was the Kohonen network. The results obtained from both networks were compared and showed that both techniques presented a high percentage of correctness to discriminate psychoactive and psychoinactive compounds. However, the Kohonen network was superior to multi-layer perceptrons.
authors.affiliation: Escola de Artes, Ciências e Humanidades, Universidade de São Paulo, 03828-0000 São Paulo, SP, Brazil.
authors.forename: Káthia M
authors.initials: KM
authors.lastname: Honório
authors.forename: Emmanuela F
authors.initials: EF
authors.lastname: de Lima
authors.forename: Marcos G
authors.initials: MG
authors.lastname: Quiles
authors.forename: Roseli A F
authors.initials: RA
authors.lastname: Romero
authors.forename: Fábio A
authors.initials: FA
authors.lastname: Molfetta
authors.forename: Albérico B F
authors.initials: AB
authors.lastname: da Silva
mesh_terms: D014150:Antipsychotic Agents / Q000737:chemistry* / Q000494:pharmacology; D002186:Cannabinoids / Q000737:chemistry* / Q000494:pharmacology; D002188:Cannabis / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D016571:Neural Networks, Computer; D021281:Quantitative Structure-Activity Relationship; D011789:Quantum Theory
chemical_list: D014150:Antipsychotic Agents; D002186:Cannabinoids