Formicapyridine-type racemates, streptovertidines A (<b>1</b>) and B (<b>2</b>), a 7,24-<i>seco</i>-fasamycin, streptovertidione (<b>3</b>), and the fasamycin-type streptovertimycins I-T (<b>4</b>-<b>15</b>), together with 13 known fasamycin congeners (<b>16</b>-<b>28</b>), were isolated from soil-derived <i>Streptomyces morookaense</i> SC1169. Their structures were elucidated by extensive spectroscopic analysis and theoretical computations of ECD spectra. The fasamycin-type compounds <b>5</b>, <b>8</b>-<b>12</b>, <b>14</b>, and <b>15</b> exhibited activity against the drug-resistant bacteria MRSA and VRE (MIC: 1.25-10.0 μg/mL). All isolates, except <b>3</b>, <b>4</b>, <b>10</b>, and <b>24</b>, displayed cytotoxicity against at least one of the human carcinoma A549, HeLa, HepG2, and MCF-7 cells (IC<sub>50</sub> < 10.0 μM), of which some were also cytotoxic to the noncancerous Vero cells. Taken together, the activity data demonstrated that the fasamycin-type compounds were more selective to the tested bacteria over the mammalian cells. Structure-activity relationship analysis suggested that chlorination at C-2 in antibacterial fasamycin-type compounds improves the activity and selectivity to the bacteria. Theoretical simulations of reaction paths and chemical reactions for conversion of <b>3</b> to <b>1</b> were carried out and supported that the pyridine ring formation in formicapyridines proceeds nonenzymatically via 1,5-dicarbonyl condensation with ammonia.