The indole and its derivatives are privileged scaffold in drug discovery as well as development. We herein report the theoretical and experimental study of ethyl 5-methyl-3-phenyl-1H-indole-2-carboxylate (5-MPIC). The solvatochromic shift method is utilized for studying the solvents’ imapct on 5-MPIC. Molecule’s emission as well as absorption spectra were obtained at room temperature (300K) in alcohol. Bakshiev, Lippert, as well as Kawaski Chamma Viallets equations have been used to produce experimental estimates for the dipole moments in the excited along with ground states. When compared to the dipole moments of the ground state, those of the excited state are bigger, proving that the excited state is more polar. The Catalan and Kamlet-Taft equations are used in the calculation of the linear solvation energy relation. We used the Gaussian 16W programme with the B3LYP 6-31+G (d, p) basis set for determining optimal molecular shape, Mulliken, NLO, HOMO-LUMO, NBO, and atomic charges. This molecule's physicochemical features, including its drug-likeness as well as bioactivity, have been determined. To learn about the compound's biophysical characteristics, molecular docking experiments were conducted using cyclooxygenase-2 (PDB ID-Cox-2).