The title compound (1), C11H9NO2, was synthesized and characterized by FT-IR, H-1 NMR, C-13 NMR spectroscopy, mass spectrometry and single crystal analysis. It was crystallized in a monoclinic system with a space group P2(1)/n. The dihedral angle between the planes of furan and benzene ring is 21.24 (11)degrees. The torsion angle of bridge -C-C-N-C-is -177.81(15)degrees. The crystal structue is stabilized by intermolecular hydrogen bonds between O-H...N and C-H...O forming a three dimensional network. The synthesized compound was screened for the in vitro antifungal against the Fusarium oxysporum f.sp albedinis FAO fungal strains and showed good activity. It was also tested for the anticancer activities against breast (MDA-MB231) and colorectal (LOVO) cancer cell lines and exhibited IC50 values of 6.9 mu g/mL and 14.6 mu g/mL, respectively. POM calculations of molecular properties of 1 are in good agreement with the mode of antifungal action of the compound bearing (X delta--Y delta-) pharmacophore site. Also it shows a drug score of 43% which is an important parameter for the compound possessing the drug character.