Hitachimycin

Hitachimycin

Systematic (IUPAC) name
(2Z,4E,6E,12E)-16,20-dihydroxy-21-methoxy- 3-methyl-10-phenyl-9-azabicyclo[17.3.0] docosa-2,4,6,12,19-pentaene-8,18-dione
Identifiers
CAS Number	77642-19-4
ATC code	none
PubChem	CID 5384563
ChemSpider	10306390
Chemical data
Formula	C29H35NO5
Molar mass	477.592 g/mol
SMILES O[C@H]1CC\C=C\C[C@H](NC(=O)\C=C\C=C\C(\C)=C/[C@H]2C[C@H](OC)C(\O)=C2\C(=O)C1)c3ccccc3
InChI InChI=1S/C29H35NO5/c1-20-11-9-10-16-27(33)30-24(21-12-5-3-6-13-21)15-8-4-7-14-23(31)19-25(32)28-22(17-20)18-26(35-2)29(28)34/h3-6,8-13,16-17,22-24,26,31,34H,7,14-15,18-19H2,1-2H3,(H,30,33)/b8-4+,11-9+,16-10+,20-17-/t22-,23-,24-,26-/m0/s1 Key:PLQKHNPZPRTISL-QSQNXQFYSA-N
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Hitachimycin, also known as stubomycin, is a cyclic polypeptide produced by Streptomyces that acts as an antibiotic. It exhibits cytotoxic activity against mammalian cells, Gram-positive bacteria, yeast, and fungi, as well as hemolytic activity; this is mediated by changes at the cell membrane and subsequent lysis.^[1] Owing to its cytotoxic activity against mammalian cells and tumors, it was first proposed as an antitumor antibiotic.^[2]

As of 2007, it has not been used in a clinical setting.

References

1. Komiyama K, Edanami K, Tanoh A, Yamamoto H, Umezawa I (1983). "Studies on the biological activity of stubomycin". J. Antibiot. 36 (3): 301–11. doi:10.7164/antibiotics.36.301. PMID 6833150.
2. Umezawa I, Takeshima H, Komiyama K, Koh Y, Yamamoto H, Kawaguchi M (1981). "A new antitumor antibiotic, stubomycin". J. Antibiot. 34 (3): 259–65. doi:10.7164/antibiotics.34.259. PMID 7275806.