QUANTITATIVE STRUCTURE-ACTIVITY
RELATIONSHIP (QSAR). IV. ANALYSIS OF THE
TOXICITY OF ALIPHATIC ESTERS BY MEANS
OF WEIGHTED HOLISTIC INVARIANT
MOLECULAR (WHIM) DESCRIPTORS.
VICENŢIU VLAIA1*, TUDOR OLARIU1, LAVINIA VLAIA2,
MARIUS BUTUR3, CIPRIAN CIUBOTARIU4, MIHAI MEDELEANU5
and DAN CIUBOTARIU1
University of Medicine and Pharmacy “Victor Babeş”, Faculty of Pharmacy
1Department of Organic Chemistry
2Department of Pharmaceutical Technology
3Department of Mathematics and Biostatistics
4Technical University “Politehnica” Timisoara, Department of Computer
Sciences
5Technical University “Politehnica” Timisoara, Department of Organic Chemistry
*corresponding author: vlaiav@yahoo.com
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Abstract:

This work presents a study of the toxicity of aliphatic esters on the Tetrahymena Pyriformis ciliate protozoan using the Weighted Holistic Invariant Molecular (WHIM) descriptors. The best QSAR (Quantitative structure-activity relationships) models reported here were obtained with six WHIM descriptors (0.910<r²<0.921), which are considered as measures of the molecular size. The predictive ability for these six models was established by internal validation, using the leave-one-out (LOO) and bootstrapping (BOOT) procedures, the cross-validation coefficients being greater than 0.900, i.e. q²>0.900. The external validation was performed on a test series of fourteen compounds (30%), randomly extracted from the whole series of aliphatic esters. The WHIM descriptors work well in predicting the toxicity of esters on T. Pyriformis: the cross-validated coefficients were q²>0.900 (LOO, BOOT) and q²_ext >0.850.

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