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Clavatols exhibit a wide range of biological activities due to their diverse structures. A genome mining strategy identified an <i>A5cla</i> cluster from <i>Penicillium</i> sp. MYA5, derived from the Arctic plant <i>Dryas octopetala</i>, is responsible for clavatol biosynthesis. Seven clavatols, including one new clavatol derivate named penicophenone F (<b>1</b>) and six known clavatols (<b>2</b>–<b>7</b>), were isolated from <i>Penicillium</i> sp. MYA5 using a transcriptome mining strategy. These structures were elucidated by comprehensive spectroscopic analysis. Antibacterial, aldose reductase inhibition, and siderophore-producing ability assays were conducted on compounds <b>1</b>–<b>7</b>. Compounds <b>1</b> and <b>2</b> demonstrated inhibitory effects on the ALR2 enzyme with inhibition rates of 75.3% and 71.6% at a concentration of 10 μM, respectively. Compound <b>6</b> exhibited antibacterial activity against <i>Staphylococcus aureus</i> and <i>Escherichia coli</i> with MIC values of 4.0 μg/mL and 4.0 μg/mL, respectively. Additionally, compounds <b>1</b>, <b>5</b>, and <b>6</b> also showed potential iron-binding ability.