A Schiff base compound 4-(E)-[2-(benzylamino)phenylimino)methyl-2]ethoxy phenol (4BPM2EP) was synthesized and its spectroscopic characterization was performed using experimental methods such as FT-IR, FT-Raman and UV-Vis spectroscopy. Density functional theory (DFT/B3LYP/6-311++G(d,p)) computation were used to investigate the optimized molecular geometry, harmonic vibrational wavenumber, NMR chemical shifts, natural bond orbital (NBO) analysis, non-linear optical (NLO) properties, molecular electroscopic potential (MEP) map, Mulliken atomic charges and thermodynamic properties of 4BPM2EP molecule. TD-DFT calculations have been carried out on the optimized geometry at gaseous phase, DMSO and ethanol to further understand the electronic transitions and solvents effect on the UV-Vis spectra of the compound. The assignments of vibrational modes were performed by means of total energy distribution (TED) using VEDA 4 program and were compared with experimental data. Molecular docking studies were performed using Schrodinger software to establish the information about the interactions between the topoisomerase DNA gyrase enzymes and the novel compound.