In this present work, we report structural and computational studies of 1,2,3-triazole fused dicarboxylate derivative (TMND), which is investigated as an angiotensin-converting enzyme (ACE) inhibitor for antihypertension treatment. The crystal structure of TMND is solved by single-crystal XRD method and correlated with density functional B3LYP/6-311++ method. We performed Hirshfeld surface analysis to examine the strength of hydrogen bonds and to measure the intercontacts and enrichment ratio. The enrichment ratio of O-H contact in TMND crystal validates (E-OH = 1.20) that the O-C and OC bonds produce four weak hydrogen bonds of the type O horizontal ellipsis H-C as evident in the supramolecular crystal packing. The enrichment ratio of C-H contacts (E-CH = 1.02) represent C-H horizontal ellipsis pi interactions with aromatic rings present in TMND crystal structure similar to XRD data. By using density functional theory (DFT/B3LYP/6-311++) method, frontier molecular orbital and molecular electrostatic potential map were computed and reactive regions were identified. In silico ACE inhibition nature of the TMND compound was evaluated using molecular docking method and followed by molecular dynamics simulation. Results reveals superior ACE inhibition ability of TMND compound over the native ligand and standard Food and Drug Administration approved antihypertensive drug lisinopril. Hence, it is concluded that our compound TMND could be considered for the antihypertensive drug design and development process.