QSAR studies on amino-succinamic acid derivatives sweeteners

Abstract

This paper presents some QSAR studies realized with the PRECLAV computer program. The database contains 3-amino-succinamic acid derivatives. The outlier molecules included in the calibration set were identified with a specific criterion. Without outliers N = 121, s = 0.3989, r2 = 0.8468, F = 128.2, KCV = 0.7700. The virtual molecular fragments that lead to a significant increase of the sweetness power SP are -CN (cyano) and -C 6H4-NHCONH- (aryl-substituted urea). The non-conjugated or weakly conjugated virtual fragment -NH2 leads to a significant decrease of the SP value. The sweetness power is favorably influenced by the size of the molecule. With a view to external validation, the calibration set includes 97 molecules (s = 0.4248, r2 = 0.8301, F = 89.9, K CV = 0.7560) and the validation set includes 24 molecules (s = 0.3836, r2 = 0.8580, K = 0.7609). Identification of molecules in validation set with high estimated value of SP is correct enough to have practical value, even if the calibration/validation set contains 3-amino-succinamic acid derivatives with very different chemical structures. ©ARKAT.