Migrastatin

Name: Migrastatin
CAS#: 314245-65-3
Chemical Formula: C27H39NO7
Exact Mass: 489.2727
Molecular Weight: 489.609
Elemental Analysis: C, 66.24; H, 8.03; N, 2.86; O, 22.87

Description: Migrastatin is a bacterial metabolite that has been found in Streptomyces with antimuscarinic and anticancer activities. It binds to M1-5 muscarinic acetylcholine receptors and inhibits calcium mobilization induced by carbamoylcholine in SK-N-SH cells, as well as in primary rat bladder smooth muscle cells. Migrastatin inhibits the migration of EC17 esophageal cancer cells in a wound healing assay and 4T1 mouse mammary carcinoma cells in a chamber cell migration assay. It enhances cytotoxicity induced by vinblastine in vincristine-resistant P388/VCR cells.

IUPAC/Chemical Name: 4-((S)-5-((2R,3Z,5R,6S,7S,8E,12E)-6-hydroxy-7-methoxy-3,5-dimethyl-14-oxooxacyclotetradeca-3,8,12-trien-2-yl)-4-oxohexyl)piperidine-2,6-dione

InChi Key: OGYMUMAKGYYNHV-IJMHZYIBSA-N

InChi Code: InChI=1S/C27H39NO7/c1-17-14-18(2)27(35-25(32)13-8-6-5-7-12-22(34-4)26(17)33)19(3)21(29)11-9-10-20-15-23(30)28-24(31)16-20/h7-8,12-14,17,19-20,22,26-27,33H,5-6,9-11,15-16H2,1-4H3,(H,28,30,31)/b12-7+,13-8+,18-14-/t17-,19-,22+,26+,27+/m1/s1

SMILES Code: O=C1NC(CC(CCCC([C@@H](C)[C@@]2(/C(C)=C\[C@@H](C)[C@H](O)[C@@H](OC)/C=C/CC/C=C/C(O2)=O)[H])=O)C1)=O

Appearance: Solid powder