Our interest in molecular representation stems from our attempts at modelling quantitative structure-(enantio)selectivity relationships (QSSR) in enantioselective chemical reactions using chiral, small molecule catalysts. Our group and others have designed a variety of alignmentdependent, molecular interaction and indicator field (MIF) descriptors intending to capture the relevant features of a chiral catalyst that lead to high enantioselectivity. A particular catalyst scaffold typically offers numerous options for analogue synthesis at well-defined positions on the structure, and each analogue then has potentially many possible conformers. Therefore, our workflow required the ability to write custom code to manipulate large collections of 3D molecular structures and perform high-throughput computations on combinatorially constructed libraries of compounds. In 2019, this laboratory released the ccheminfolib toolkit, an early iteration of a software package designed to handle combinatorial construction of large in silico libraries. One of the main motivations for the creation of a new software package was to establish a modern, convenient and extensible interface that would allow rapid prototyping of chemical libraryoriented workflows. Since the release of ccheminfolib, we sought to address the following problems: