Guided Iterative Substructure Search (GI-SSS) - A New Trick for an Old Dog

Substructure search (SSS) is a fundamental technique supported by various chemical information systems. Many users apply it in an iterative manner: they modify their queries to shape the composition of the retrieved hit sets according to their needs. We propose and evaluate two heuristic extensions of SSS aimed at simplifying these iterative query modifications by collecting additional information during query processing and visualizing this information in an intuitive way. This gives the user a convenient feedback on how certain changes to the query would affect the retrieved hit set and reduces the number of trial‐and‐error cycles needed to generate an optimal search result. The proposed heuristics are simple, yet surprisingly effective and can be easily added to existing SSS implementations.