By modifying functional groups while retaining features of the parent structure, transformation rules enable the exploration of new chemical derivatives . In this project, we applied 376 transformation rules to the chemical structures of compounds 2-4. The transformations consisted of 175 rules initially implemented in MOE 2023 plus 201 additional rules constructed by with two iterations. The following restrictions were applied: MW≤500 Da, TPSA between 40 and 140 Å 2 , absence of reactive groups, and synthetic feasibility greater than 0.4 (where 0 indicates unlikely to synthesize and 1 indicates easier to synthesize), implemented in MOE. The application of the transformation rules with the aforementioned restrictions led to a total of 172,026 new chemical structures (Figure ). Thus, 2 generated structures in a dataset herein named diarylcore dataset (DIADS), while 3 and 4 gave rise to the indole-core dataset (INDDS) and the pyridone-core dataset (PYRDS), respectively.