In summary, we have shown that borrowing tools from reaction informatics provides an opportunity to map multiple similarity relationships between molecules simultaneously and gain insights into interesting drug pairs that are otherwise difficult to identify. Specifically, we used DRFP to map the chemical space of multiple drug pairs selected as being similar according to eight different molecular fingerprints simultaneously in the form of TMAPs. We then used RXNMapper to visualize the structural changes between drugs and identify pairs of drugs related by feasible chemical transformation from pairs related by alchemical changes corresponding to multiple and complex structural rearrangements. These tools should generally be applicable to analyze drug sets from multiple angles in the context of drug discovery.