A novel descriptor based on atom-pair properties

Molecular descriptors have been widely used to predict biological activities and physicochemical properties or to analyze chemical libraries on the basis of similarity. Although fingerprints and properties are generally used as descriptors, neither is perfect for these purposes. A fingerprint can distinguish between molecules, whereas a property may not do the same in certain cases, and vice versa. When the number of the training set is especially small, the construction of good predictive models is difficult. Herein, a novel descriptor integrating mutually compensating fingerprint and property characteristics is described. The format of this descriptor is not conventional. It has two dimensions with variable length in one dimension to represent one molecule. This format is not acceptable for any machine learning methods. Therefore the distance between molecules has been newly defined for application to machine learning techniques. The evaluation of this descriptor, as applied to classification tasks, was performed using a support vector machine after the features of the descriptor had been optimized by a genetic algorithm.

Because the optimizing feature is time-intensive due to the complicated calculation of distances between molecules, the optimization was forced to stop before it was completed. As a result, no remarkable improvement was observed in the classification results for the new descriptor compared with those for other descriptors in any evaluation set used in this work. However, extremely low accuracies were also not found for any set.

The novel descriptor proposed in this work can potentially be used to make highly accurate predictive models. This new concept in descriptors is expected to be useful for developing novel predictive methods with quick training and high accuracy.