Diversity and Chemical Library Networks of Large Data Sets

The quantification of chemical diversity has many applications in drug discovery, organic chemistry, food, and natural product chemistry, to name a few. As the size of the chemical space is expanding rapidly, it is imperative to develop efficient methods to quantify the diversity of large and ultralarge chemical libraries and visualize their mutual relationships in chemical space. Herein, we show an application of our recently introduced extended similarity indices to measure the fingerprint-based diversity of 19 chemical libraries typically used in drug discovery and natural products research with over 18 million compounds. Based on this concept, we introduce the Chemical Library Networks (CLNs) as a general and efficient framework to represent visually the chemical space of large chemical libraries providing a global perspective of the relation between the libraries. For the 19 compound libraries explored in this work, it was found that the (extended) Tanimoto index offers the best description of extended similarity in combination with RDKit fingerprints. CLNs are general and can be explored with any structure representation and similarity coefficient for large chemical libraries.

Automated summary

The quantification of chemical diversity has extensive applications across various fields. With the expansion of chemical libraries, it is crucial to develop efficient methods for quantifying and visualizing the diversity of large-scale chemical libraries. This article introduces a new extended similarity indices method to measure the fingerprint-based diversity of chemical libraries and proposes the Chemical Library Networks (CLNs) framework for visually representing the chemical space of large libraries.