Drugs with post-prandial action constitute one of the main course of treatments for diabetes. In the present investigation, we have explored the α-amylase inhibitory potential of ethanolic extract of Cocos nucifera endocarp. DNS based α-amylase assay indicated that IC50 value of extract lies in the range of 63-126 µg/ml and at higher doses, i.e. above 250 µg/ml, it is having better α-amylase inhibition than the standard drug, acarbose. Phytochemical screening indicated that ethanolic extract is rich in alkaloids, tannins, flavonoids, saponins, triterpenes, glycosides, carbohydrates, terpenoids, quinones and lactones. Further, GC-MS analysis (where Similarity Index was>> 90) predicted that the probable phytoconstituents present in the ethanolic extract are myristic acid, syringaldehyde, eugenol, vanillin, 2,4-di-tert-butylphenol, lauric acid, palmitic acid methyl ester and γ-sitosterol. In silico docking studies were done using VLife MDS 4.6 software and the probable molecules, predicted after GC-MS analysis, were docked with the co-crystallized (acarbose) tracked active site and rest all cavities of porcine pancreatic α-amylase (1OSE). γ-Sitosterol have shown the strong affinity towards the active site which was tracked by co-crystallized ligand along with cavity 1 and 2 while significant interactions were observed in case of co-crystallized tracked active site as well as cavity 4 of 1OSE. ADMET analysis was done using StarDrop 6.4, Derek Nexus and P450 Modules from Optibrium Ltd. and LHASA Ltd. Ethanolic extract of C. nucifera has no haemolytic effect. Its ability to effectively inhibit α-amylase may be attributed to the presence of the above probable molecules, which will be explored further.