Migrastatin

Migrastatin is an organic compound which naturally occurs in the Streptomyces platensis bacteria. Migrastatin and several of its analogues (including Isomigrastatin) have shown to have potential in treating cancer, as it inhibits the metastasis of cancer cells.[1]

Migrastatin
Migrastatin
Names
Preferred IUPAC name
4-{(5S)-5-[(2R,3Z,5R,6S,7S,8E,12E)-6-Hydroxy-7-methoxy-3,5-dimethyl-14-oxo-1-oxacyclotetradeca-3,8,12-trien-2-yl]-4-oxohexyl}piperidine-2,6-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • 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 checkY
    Key: OGYMUMAKGYYNHV-IJMHZYIBSA-N checkY
  • InChI=1/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
    Key: OGYMUMAKGYYNHV-IJMHZYIBBB
  • C[C@@H]1/C=C(\[C@H](OC(=O)/C=C/CC/C=C/[C@@H]([C@H]1O)OC)[C@H](C)C(=O)CCCC2CC(=O)NC(=O)C2)/C
Properties
C27H39NO7
Molar mass 489.60 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Shan, D; et al. (2005). "Synthetic analogues of migrastatin that inhibit mammary tumor metastasis in mice". PNAS. 102 (10): 3772–3776. Bibcode:2005PNAS..102.3772S. doi:10.1073/pnas.0500658102. PMC 553334. PMID 15728385.
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