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The phytochemical investigation of the methanolic extracts of roots, stem bark, leaves and twigs of Manilkara obovata has led to the isolation of one new friedelane triterpene, lacefriedelic acid or 3β,23-dihydroxy D:A-friedooleanan-28-oic acid (1) and one new prenylated xanthone, lacexanthone or 4,7-dihydroxy-2,3,3,9,9-pentamethyl-2,2-dihydrofurano[2,3-a]pyrano[2,3-i]xanthen-13(9H)-one (2) alongside twenty-four known compounds. Compounds 1-11 are reported here for the first time from the genus Manilkara. The structures of all compounds were determined by spectroscopic analyses and X-ray crystallography. The methanolic extracts of twigs and leaves showed anti-oxidant activity of 93.2 and 91.1%, respectively, at 100 µg/mL when measured by DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate), while the twig extract displayed 86.3% at 100 µg/mL against the urease inhibition assay. Some isolated compounds (1-4, 15 and 20) showed significant to moderate anti-oxidant activity and urease inhibition assay. It is estimated that significantly active anti-oxidants and urease inhibitors metabolized by the plant may find future application in food industry.