Molecular dataset diversity indices and their applications to comparison of chemical databases and QSAR analysis

A new mutual molecular dataset diversity index (MMDDI), individual molecular dataset diversity index (IMDDI), and volume ratio (VR) are proposed to assess molecular dataset diversity. MMDDI and IMDDI can serve as valuable instruments for selecting monomer pools for combinatorial synthesis and in decision making about acquiring new databases. MMDDI can also be used as one of the criteria to estimate the quality of quantitative structure-activity relationship (QSAR) models aimed at the prediction of biological activities. The indices can be calculated directly from molecular descriptor values. The procedures applied for MMDDI and IMDDI calculations allow one to automatically compile lists of compounds, which can simplify molecular diversity analyses and database searching. The information can also be used for forming training and test sets in QSAR analysis.