aug-MIA-QSPR on the modeling of sweetness values of disaccharide derivatives

Multivariate image analysis applied to quantitative structure–property relationships (MIA-QSPR) was used to model the sweetness values relative to sucrose, log (RS), of a series of 40 disaccharides. Two dimensional molecular shape and atomic sizes were capable of predicting the changes in log (RS), giving results of calibration (R2 = 0.97) and validation (R2CV = 0.86 and R2test = 0.94) very satisfactory. A novel polyhalogenated derivative with high estimated sweetness was proposed and a glucophoric pattern based on the well-known AH-B-γ system has been discussed. The technique avoids unnecessary time and cost-demanding procedures, since new compounds (e.g. food additives) can be designed and their property estimated prior to compound preparation.

► MIA-QSAR was applied to model sweetness of a series of disaccharides.
► Molecular shape and atomic sizes were capable of encoding accurately the sweetness.
► A novel polyhalogenated derivative with high estimated sweetness was proposed.
► MIA-QSPR is an effective approach in active compound development.
► New compounds can be designed and their property estimated prior to preparation.