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Five new compounds named asperpenes A-C (<b>1</b>&#8315;<b>3</b>), 12,13-dedihydroversiol (<b>4</b>), and methyl 6-oxo-3,6-dihydro-2<i>H</i>-pyran-4-carboxylate (<b>5</b>), along with 10 known compounds (<b>6</b>&#8315;<b>15</b>), were isolated from the fermentation broth of <i>Aspergillus</i> sp. SCS-KFD66 associated with a bivalve mollusk, <i>Sanguinolaria chinensis</i>, collected from Haikou Bay, China. The structures of the compounds, including the absolute configurations of their stereogenic carbons, were unambiguously determined by spectroscopic data, single-crystal X-ray diffraction analysis, and electronic circular dichroism (ECD) spectral analysis, along with quantum ECD calculations. The growth inhibitory activity of the compounds against four pathogenic bacterial (<i>Escherichia coli</i> ATCC 25922, <i>Staphylococcus aureus</i> ATCC 6538, <i>Listeria monocytogenes</i> ATCC 1911, and <i>Bacillus subtilis</i> ATCC 6633), their enzyme inhibitory activities against acetylcholinesterase and &#945;-glucosidase, and their DPPH radical scavenging activity were evaluated.