Magic Rings: Navigation in the Ring Chemical Space Guided by the Bioactive Rings

The large majority of bioactive molecules
contain a more or less
complex ring system as a central structural element. This central
core determines the basic molecule shape, keeps substituents in their
proper positions, and often also contributes to the biological activity
itself. In this study the ring systems extracted from one billion
molecules are processed and differences between rings from bioactive
molecules and common synthetic molecules are analyzed. The bioactive
rings seem to be distributed throughout the large portion of chemical
space, but not uniformly; one can see several more dense regions,
where the bioactive rings often appear in small clusters, as well
as empty areas. A web tool offering an interactive navigation in the
ring chemical space and supporting identification of bioisosteric
ring analogs available at https://bit.ly/magicrings is also described.