Phytochemical characterization of the polar fraction of Erigeron annuus extract led to the isolation of glycerylerigeroside (1), a unique -pyrone derivative. Structure of 1 was decided by intensive study of NMR and mass spectra as 3-O-[4'-((1,3-dihydroxypropan-2-yl)oxy)--Dglucopyranoside)]-4H-pyran-4-one, with uncommon glyceroxy side chain attached to 4' position of pyromeconic acid-D-glucopyranoside. Antimicrobial potential of 1 was tested against Staphylococcus aureus, Salmonella enterica, and Candida albicans. Compound 1 strongly inhibited growth of Candida albicans (MIC = 17.24 µM/disk), compared to fluconazole (MIC = 16.33 µM/disk). Meanwhile, it moderately inhibited the growth of Staphylococcus aureus (MIC = 71.84 M/disk) and Salmonella enterica (MIC = 71.84 µM/disk), as compared with thiophenicol (MIC = 14.05 M/disk) and (MIC = 14.05 M/ disk), respectively. The binding mode of 1 with the active site of sterol 14-demethylase (CYP51) from Candida albicans (PDB ID: 5TZ1), in combination with fluconazole, was predicted by molecular docking study and supported the antifungal activity.