Rings and ring systems are important structural features of the drug-like chemical space and much of the effort in the field of organic synthesis has been directed towards creation of novel and “interesting” ring moieties. It has proven a challenge however to venture out into the ring space beyond the familiar structural features that number in no more than seventy thousand or so. The goal of the Synthetically Accessible Virtual Inventory (SAVI) project is to expand the horizons of known chemistry by generating a large virtual library of easily and cheaply synthesizable drug-like compounds. Realizing the importance of the ring chemistry, especially in the context of drug design, one of the chief points in the SAVI strategy is steering of its compound generation protocols towards exploration of novel ring space. Although SAVI utilizes common, easily accessible building blocks from a major chemical supplier as starting materials and well-established ubiquitous chemistry, we show that it is able to create novel rings at a substantial rate. We analyze the makeup of the SAVI-generated ring universe with respect to aromatics, aliphatics, and heterocycles and identify which chemical reactions in the context of SAVI are most productive when it comes to generating rings of a particular type as well as creating novel rings in general. Additionally, we look into potential strategies to drive SAVI’s ring exploration even further as well as assess its ability to generate ring features found in natural products and natural product-like compounds.

Novel rings in the synthetically accessible virtual inventory (SAVI)

252nd National Meeting (2016)

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