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Four compounds (<b>1</b>&#8722;<b>4</b>) were isolated from the extracts of <i>Streptomyces</i> sp. CT37 using bioassay in conjunction with mass spectrometric molecular networking (MN) driven isolation. Their complete structures were established by high-resolution electrospray ionization mass spectrometry (HR-ESIMS), and 1D and 2D nuclear magnetic resonance (NMR) data. Legonimide <b>1</b> was identified as a new alkaloid containing a rare linear imide motif in its structure, while compounds <b>2&#8722;4</b> were already known and their structures were elucidated as 1H-indole-3-carbaldehyde, actinopolymorphol B, (<i>2R,3R</i>)-1-phenylbutane-2,3-diol, respectively. The biosynthetic pathways of <b>1&#8722;4</b> were proposed based on the reported biogenesis of indole alkaloids in literature. Bioactivity tests for <b>1</b> and <b>2</b> revealed moderate growth inhibition activity against <i>Candida albicans</i> ATCC 10231 with MIC₉₅ values of 21.54 &#181;g/mL and 11.47 &#181;g/mL, respectively.