Unsupervised machine learning techniques (K-means clustering, Gaussian Mixture Models) were used to assign clusters based on three principal components of the lower triangular pairwise distance matrix (Figure ). Based on the DFT calibration, PBE/cc-pVTZ was chosen as the method basis set combination to compute logPtol/w with the structures sampled from the clusters generated via unsupervised machine learning and the conformations from Spartan.