The chromatographic separation of the components of the acetone extract of <i>Mallotus philippensis</i> fruits yielded five new phenolic compounds including two chalcones, <b>1</b> and <b>3</b>, a functionalized phloroglucinol, <b>2</b>, two flavanones, <b>4</b> and <b>5</b>, and six known compounds. The structures of <b>1</b>-<b>5</b> were confirmed by NMR and mass analyses. Racemic compounds <b>1</b> and <b>2</b> were separated by chiral-phase HPLC, and the absolute configuration of (+)-<b>1</b> was confirmed by X-ray diffraction studies and ECD spectroscopic data. The configurations of the enantiomers of <b>2</b> were defined by comparison of its ECD data with those of (+)-<b>1</b>. Compounds <b>6</b> and <b>7</b> exhibited significant antibacterial activities, with MIC values ranging from 3.8 to 15.5 μM.