Supplementary material includes details on the functional form of the CG FF within which the parameters are optimized, the molecular models used in these experiments, their topologies, their optimized FF parameters obtained with SwarmCG in the context of Representations 1 and 2, as well as the implementation for usage with HPC resources. Additional details are also provided concerning the submolecular features observed in the CG models obtained at the end of the optimization experiments, underlining the relevance of the OT-B metrics.