Migrastatin

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
CAS Number
  • 314245-65-3 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:66389
ChEMBL
  • ChEMBL474321 checkY
ChemSpider
  • 21106454 checkY
PubChem CID
  • 11016431
CompTox Dashboard (EPA)
  • DTXSID70904046 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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
Chemical compound

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]

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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