Three previously undescribed compounds named heimiomycin A-C (1-3), featuring a unique scaffold with calamenene connected to a hydroxystyryl-pyranone moiety, along with the new calamenene derivatives 4 and 5 and phenanthridine derivative (6) were obtained from a culture of a Heimiomyces sp. This is the first report of the occurrence of calamenene-type terpenoids in fungi. Compound 3 exhibited antimicrobial activity against Gram-positive bacteria and Mucor hiemalis. Compounds 1 and 3 displayed moderate cytotoxicity against KB 3.1 and L929 cell lines, respectively.