A 3D-QSAR STUDY OF ANALOGS OF (Z)-5-DECENYL ACETATE, A PHEROMONE COMPONENT OF THE TURNIP MOTH, AGROTIS-SEGETUM

The methodology of three-dimensional quantitative structure-activity r elationships (3D-QSAR) has been employed to develop a quantitative mod el for the relationship between single-cell activities for a large set of analogs of (Z)-5-decenyl acetate, a pheromone component of the tur nip moth, Agrotis segetum, and the structural characteristics of the a nalogs. The method of partial least squares (PLS) projections to laten t structures has been used to delineate the relationships between meas ured activities and chemical structures. The training set includes 42 compounds, and a test set of seven molecules has been employed to asse ss the predictivity of the model. The model derived is able to calcula te the activities of the seven test compounds with an average unsigned error of 0.3, close to the experimental error. Contour maps of regres sion-like coefficients from transformed PLS components display electro nic and nonbonded features of high importance for the observed variati on in the activities of compounds in the training set. The contours fo r the nonbonded (van der Waals) field support previous conclusions tha t the interaction between the pheromone component and its receptor is characterized by a high steric complementarity.