High energy compounds rich in nitrogen have accepted significant attention at present for their potential applications as explosives. Pentagonal heterocycles rich in nitrogen, such as oxadiazoles are preferred as High Energy Density Materials (HEDMs) because of the imine and nitroxyl bonds in their ring enhance both oxygen balance and heat of formation (HOF). Computational screening is an appealing approach for discovering new materials, as it provides a cost-effective means of evaluating compounds before synthesis. The present study involved the design and optimization of energetic compounds by incorporating different energetic substituent groups to 1,2,4-oxadiazole backbone. The designed compounds are evaluated for HOF, density, detonation performance, electronic structures and impact sensitivity. The detonation performance of optimized compounds was calculated using Kamlet-Jacobs equations. The impact sensitivity of HEDMs is evaluated in terms of impact energy (EI). The introduction of nitro and azido group to the oxadiazole compound has resulted in energetic materials with greater detonation performance and lower sensitivity than RDX and HMX. Four compounds may be selected as potential candidates for HEDMs.