Syzygium zeylanicum (L.) DC (S. zeylanicum) is a member of the Myrtaceae family. Phytochemicals found in the plant, such as flavonoids, phenols, and saponin, may have antioxidant and anti-diabetic properties. A flavonoid, 2,3,13,14,15-penta hydroxyl 5,11-dioxo1,2,3,4,4a,5,6,7,10,11,16,16 and dodeca hydro-6,10-epoxy dibenzo[a,d][12]annulen7-yl 3oxo-4-(2,3,4-trihydroxycyclhexyl)butanoate, were isolated from Syzygium zeylanicum by column chromatography and characterized using advanced analytical techniques such as 1H NMR, 13C NMR, mass spectrometry, and FT-IR. This flavonoid was screened in-silico against antidiabetic targets viz., α-Amylase, α-Glucosidase, Peroxisome proliferator-activated receptor gamma (PPAR-γ), Glycogen synthase kinase 3-beta (GSK3-β), Dipeptidyl peptidase4 (DPP-4), Fibroblast growth factor (FGF), and Matrix metalloproteinase-1 (MMP1). Molecular dynamics simulation and binding affinity analysis suggested that the ligand exhibits strong and stable binding with several critical proteins involved in glucose metabolism and insulin regulation. The potential of this ligand to inhibit these enzymes makes it a promising candidate for developing novel therapeutic agents for diabetes and related metabolic disorders. The overall binding profile supports the potential of the compound as an antidiabetic agent via multiple mechanisms, including enzyme inhibition, enhanced insulin secretion, and improved insulin sensitivity. Further experimental validation is necessary to confirm these predictions and elucidate the pharmacological effects of the compound