This worked example uses Inspyra™ to interactively explore optimisation strategies to achieve a selective inhibitor of DPP-4 with appropriate physicochemical properties. Starting from a data set of compounds representing three chemical series based on pyrrolidine, cyanopyrrolidine, piperazine and 1,4-diazepane cores, we will explore approaches to expand on the diversity of compounds in the data set and consider design strategies around a specific compound of interest.