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Cepharanoline

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Cepharanoline
Names
IUPAC name (14S,27R)-33-Methoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclononatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dodecaen-22-ol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C36H36N2O6/c1-37-12-10-23-17-31(40-3)32-19-26(23)27(37)15-22-6-9-29(39)30(16-22)43-25-7-4-21(5-8-25)14-28-34-24(11-13-38(28)2)18-33-35(36(34)44-32)42-20-41-33/h4-9,16-19,27-28,39H,10-15,20H2,1-3H3/t27-,28+/m1/s1Key: VQAWRQZAAIQXHM-IZLXSDGUSA-N
  • InChI=1/C36H36N2O6/c1-37-12-10-23-17-31(40-3)32-19-26(23)27(37)15-22-6-9-29(39)30(16-22)43-25-7-4-21(5-8-25)14-28-34-24(11-13-38(28)2)18-33-35(36(34)44-32)42-20-41-33/h4-9,16-19,27-28,39H,10-15,20H2,1-3H3/t27-,28+/m1/s1Key: VQAWRQZAAIQXHM-IZLXSDGUBD
SMILES
  • CN1CCC2=CC3=C(C4=C21CC5=CC=C(C=C5)OC6=C(C=CC(=C6)C7C8=CC(=C(C=C8CCN7C)OC)O4)O)OCO3
Properties
Chemical formula C36N2O6
Molar mass 556.404 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Cepharanoline is an isolate of Stephania that has antiplasmodial activity with an IC50 of 0.2 μM.

References

  1. Aun Chea, Sok-Siya Bun, Nadine Azas, Monique Gasquet, Sothavireak Bory, Evelyne Ollivier, Riad Elias (2010). "Antiplasmodial activity of three bisbenzylisoquinoline alkaloids from the tuber of Stephania rotunda". Nat Prod Res. 24 (18): 1766–70. doi:10.1080/14786410903395624. PMID 20981617. S2CID 8317046.{{cite journal}}: CS1 maint: multiple names: authors list (link)


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