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Sceptrin

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Sceptrin
Names
Systematic IUPAC name N,N′-{bis(methylene)}bis(4-bromopyrrole-2-carboxamide)
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C22H24Br2N10O2/c23-9-1-13(27-3-9)19(35)29-5-11-12(6-30-20(36)14-2-10(24)4-28-14)18(16-8-32-22(26)34-16)17(11)15-7-31-21(25)33-15/h1-4,7-8,11-12,17-18,27-28H,5-6H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t11-,12-,17-,18-/m1/s1Key: YPZNLFZLPZWWAD-GWIYSAMLSA-N
  • InChI=1/C22H24Br2N10O2/c23-9-1-13(27-3-9)19(35)29-5-11-12(6-30-20(36)14-2-10(24)4-28-14)18(16-8-32-22(26)34-16)17(11)15-7-31-21(25)33-15/h1-4,7-8,11-12,17-18,27-28H,5-6H2,(H,29,35)(H,30,36)(H3,25,31,33)(H3,26,32,34)/t11-,12-,17-,18-/m1/s1Key: YPZNLFZLPZWWAD-GWIYSAMLBB
SMILES
  • C1=C(NC=C1Br)C(=O)NC2((2C3=CN=C(N3)N)C4=CN=C(N4)N)CNC(=O)C5=CC(=CN5)Br
Properties
Chemical formula C22H24Br2N10O2
Molar mass 620.310 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Sceptrin is a bioactive marine isolate. It has been isolated from the marine sponge Agelas conifera and appears to have affinity for the bacterial actin equivalent MreB. As such, this compound possess antibiotic potential.

See also

References

  1. Cipres, A; O'Malley, DP; Li, K; Finlay, D; Baran, PS; Vuori, K (2010). "Sceptrin, a marine natural compound, inhibits cell motility in a variety of cancer cell lines". ACS Chemical Biology. 5 (2): 195–202. doi:10.1021/cb900240k. PMC 2825093. PMID 20030414.
  2. Rodriguez, AD; Lear, MJ; La Clair, JJ (2008). "Identification of the binding of sceptrin to MreB via a bidirectional affinity protocol". J Am Chem Soc. 130 (23): 7256–7258. doi:10.1021/ja7114019. PMID 18479102.
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