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Three new phenols (<b>1</b>–<b>3</b>), one new cyclohexanol (<b>4</b>), two known phenols (<b>5</b>–<b>6</b>), and six known flavonoids (<b>7</b>–<b>12</b>) were isolated from the <i>n</i>-butanol of the 75% ethanol extract of all plants of <i>Chimaphila japonica</i> Miq. Among them, compound <b>5</b> was named and described in its entirety for the first time, and compounds <b>9</b> and <b>10</b> were reported in <i>C. japonica</i> for the first time. The structures of all compounds were confirmed using a comprehensive analysis of 1D and 2D NMR and HRESIMS data. Biological results show that compounds <b>4</b>, <b>7</b>, and <b>11</b> exhibited potent diuretic activity. The modes of interaction between the selected compounds and the target diuretic-related WNK1 kinase were investigated in a preliminary molecular docking study. These results provided insight into the chemodiversity and potential diuretic activities of metabolites in <i>C. japonica</i>.