title: Simplified molecular input-line entry system and International Chemical Identifier in the QSAR analysis of styrylquinoline derivatives as HIV-1 integrase inhibitors.
abstract: The simplified molecular input-line entry system (SMILES) and IUPAC International Chemical Identifier (InChI) were examined as representations of the molecular structure for quantitative structure-activity relationships (QSAR), which can be used to predict the inhibitory activity of styrylquinoline derivatives against the human immunodeficiency virus type 1 (HIV-1). Optimal SMILES-based descriptors give a best model with n = 26, r(2) = 0.6330, q(2) = 0.5812, s = 0.502, F = 41 for the training set and n = 10, r(2) = 0.7493, r(pred)(2) = 0.6235, R(m)(2) = 0.537, s = 0.541, F = 24 for the validation set. Optimal InChI-based descriptors give a best model with n = 26, r(2) = 0.8673, q(2) = 0.8456, s = 0.302, F = 157 for the training set and n = 10, r(2) = 0.8562, r(pred)(2) = 0.7715, R(m)(2) = 0.819, s = 0.329, F = 48 for the validation set. Thus, the InChI-based model is preferable. The described SMILES-based and InChI-based approaches have been checked with five random splits into the training and test sets.
authors.affiliation: Istituto di Ricerche Farmacologiche Mario Negri, Via La Masa 19, 20156 Milano, Italy.
authors.forename: Alla P
authors.initials: AP
authors.lastname: Toropova
authors.forename: Andrey A
authors.initials: AA
authors.lastname: Toropov
authors.forename: Emilio
authors.initials: E
authors.lastname: Benfenati
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Gini
mesh_terms: D015658:HIV Infections / Q000188:drug therapy / Q000821:virology; D019427:HIV Integrase / Q000378:metabolism*; D019428:HIV Integrase Inhibitors / Q000032:analysis* / Q000138:chemical synthesis / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009010:Monte Carlo Method; D021281:Quantitative Structure-Activity Relationship; D011804:Quinolines / Q000032:analysis* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D019428:HIV Integrase Inhibitors; D011804:Quinolines; C481600:styrylquinoline; D019427:HIV Integrase; C514801:p31 integrase protein, Human immunodeficiency virus 1