A chemical reinvestigation of the Indonesian strain <i>Streptomyces</i> sp. SHP 22-7 led to the isolation of three new pyrimidine nucleosides, along with six known analogues and zincphyrin. The structures of the new compounds (<b>6</b>, <b>7</b>, <b>10</b>) were elucidated by employing spectroscopic techniques (NMR, MS, CD, and IR) as well as enantioselective analyses of methyl branched side chain configurations. Application of the precursor-directed feeding approach led to the production and partial isolation of nine further pyrimidine analogues. The new compounds <b>6</b>, <b>7</b>, and <b>11</b> and three of the known compounds (<b>2</b>-<b>4</b>) were found to possess antimycobacterial and cytotoxic properties.