Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase

ROJAS, C.; DUCHOWICZ, P. R.; TRIPALDI, P.; PIS DIEZ, R.

JOURNAL OF CHROMATOGRAPHY - A

ELSEVIER SCIENCE BV

Lugar: Amsterdam; Año: 2015 vol. 1422 p. 277 - 288

0021-9673

A quantitative structure?property relationship (QSPR) was developed for modeling the retention indexof 1184 flavor and fragrance compounds measured using a Carbowax 20M glass capillary gas chromatog-raphy column. The 4885 molecular descriptors were calculated using Dragon software, and then weresimultaneously analyzed through multivariable linear regression analysis using the replacement method(RM) variable subset selection technique. We proceeded in three steps, the first one by considering all descriptor blocks, the second one by excluding conformational descriptor blocks, and the last one byanalyzing only 3D-descriptor families. The models were validated through an external test set of com-pounds. Cross-validation methods such as leave-one-out and leave-many-out were applied, togetherwith Y-randomization and applicability domain analysis. The developed model was used to estimate theI of a set of 22 molecules. The results clearly suggest that 3D-descriptors do not offer relevant informationfor modeling the retention index, while a topological index such as the Randi´c-like index from reciprocalsquared distance matrix has a high relevance for this purpose.