MARS Plus: An Improved Molecular Design Tool for Complex Compounds Involving Ionic, Stereo, and Cis–Trans Isomeric Structures

MARS (Molecular Assembling and Representation Suite) (Hsu et al. J. Chem. Inf. Model. 2019, 59, 3703–3713) is a toolbox for the molecular design of organic molecules. MARS uses integer arrays to represent the elements and connectivity between elements of a molecule. It provides a collection of operations to manipulate the elemental composition and connectivity of a molecule (or a pair of molecules), enabling the creation of novel chemical compounds. In this work, the original MARS is extended to handle complex molecular structures, including geometric (cis–trans) isomers, stereo isomers, cyclic compounds, and ionic species. The extended version of MARS, referred to as MARS+, has a more comprehensive coverage of the chemical space and therefore can explore molecules with a greater chemical and physical diversity. Compared to other molecular design tools, MARS+ is designed to perform all possible manipulations on a given molecule or a pair of molecules. Molecular structure manipulation can be conducted in either a controlled or a random fashion. Furthermore, every structure manipulation has a counterpart so that the operation can be reversed. Nearly any possible chemical structure can be generated with MARS+ via a combination of molecular operations. The capabilities of MARS+ are examined by the design of new ionic liquids (ILs). The results show that MARS+ is a useful tool for computer-aided molecular design (CAMD) and molecular structure enumeration.