Ecotoxicity prediction by adaptive fuzzy partitioning: comparing descriptors computed on 2D and 3D structures

Classification models were established on four endpoints, i.e. trout, daphnia, quail and bee, including from 100 to 300 pesticides subdivided into 3 toxicity classes. For each species, five separate sets of molecular descriptors, computed by several software, were compared, including parameters related to 2D or 3D structures. The most relevant descriptors were selected with help of a procedure based on genetic algorithms. Then, structure-activity relationships were built by Adaptive Fuzzy Partition (AFP), a recursive partitioning method derived from Fuzzy Logic concepts. Globally, satisfactory results were obtained for each animal species. The best crossvalidation and test set scores reached values of about 70-75%. More important, the relationships derived from the descriptors calculated from 2D structures were superior or similar to those computed from 3D structures. These results underline that the long computational time employed to compute 3D descriptors is often useless to improve the prediction ability of the ecotoxicity models. Finally, the differences in the prediction ability between the different software used were quite reduced and show the possibility to use different descriptor packages for obtaining similar satisfactory models.