Name: Inostamycin A
CAS#: 129905-10-8
Chemical Formula: C38H68O11
Exact Mass: 700.4762
Molecular Weight: 700.951
Elemental Analysis: C, 65.11; H, 9.78; O, 25.11
Description: Inostamycin A is a bacterial metabolite that has been found in Streptomyces and has anticancer activity. It is an inhibitor of CDP-diacylglycerol:inositol 3-phosphatidyltransferase (IC50 = 0.02 µg/ml in A431 cell membranes) and is selective for CDP-diacylglycerol:inositol 3-phosphatidyltransferase over phospholipase C (PLC) and phosphatidylinositol kinase at 10 µg/ml. Inostamycin A decreases viability of YCU-T892, KCC-TC873, KB, HSC-4, and YCU-T891 oral squamous cell carcinoma (OSCC) cells in a concentration-dependent manner. It induces cell cycle arrest in the G1 phase in HSC-4 cells when used at a concentration of 250 ng/ml and induces apoptosis in Ms-1 small cell lung cancer cells at 300 ng/ml. Inostamycin A also reduces levels of matrix metalloproteinase-2 (MMP-2) and MMP-9 and inhibits EGF-induced migration of HSC-4 cells.
IUPAC/Chemical Name: (R)-2-((2R,3S,4R,5S,6R)-5-ethyl-6-((2S,3S,4S,6R)-6-((2S,2'R,3'R,4S,5S,5'R)-5'-ethyl-2'-hydroxy-5'-((S)-1-hydroxybutyl)-2,3',4-trimethyloctahydro-[2,2'-bifuran]-5-yl)-3-hydroxy-4-methyl-5-oxooctan-2-yl)-2,4-dihydroxy-3-methyltetrahydro-2H-pyran-2-yl)butanoic acid
InChi Key: NZJHONRWXITMMC-LPMSCSBASA-N
InChi Code: InChI=1S/C38H68O11/c1-12-17-28(39)36(16-5)19-21(7)38(46,49-36)35(11)18-20(6)32(47-35)25(13-2)30(41)22(8)29(40)23(9)33-26(14-3)31(42)24(10)37(45,48-33)27(15-4)34(43)44/h20-29,31-33,39-40,42,45-46H,12-19H2,1-11H3,(H,43,44)/t20-,21+,22-,23-,24-,25-,26-,27-,28-,29+,31-,32-,33+,35-,36+,37+,38+/m0/s1
SMILES Code: O[C@]1([C@@](C[C@@H]2C)(C)O[C@@]2([C@H](C([C@H]([C@H]([C@H](C)[C@]([H])([C@@H](CC)[C@@H](O)[C@@H]3C)O[C@]3([C@H](C(O)=O)CC)O)O)C)=O)CC)[H])[C@H](C)C[C@](CC)([C@H](CCC)O)O1
Appearance: Solid powder
