Based on structural diversity and wide biological activity range, four chymase inhibitors including most and least active compounds, were selected from the training set. While, three final hits BTB02076, HTS12673, JFD00311 retrieved from Maybridge database by the selected pharmacophore model, which showed important results with respect to all properties like molecular interactions with the active site components, estimated activity, calculated drug-like properties, and high GOLD fitness score, were also selected. Thus, data set employed for DFT study consisted of seven compounds. Various quantum-chemical descriptors such as LUMO, HOMO, and locations of molecular electrostatic potentials (MESP), were computed.