19022-51-6
Chemical Structure
Ophiobolin C
Synonym(s): Zizanin A
- CAS No.: 19022-51-6
- Formula:C25H38O3
- Molecular Weight:386.57
IUPAC Name: (1R,3aS,6aS,7R,9aR,10aS,E)-1-hydroxy-1,9a-dimethyl-7-((S)-6-methylhept-5-en-2-yl)-3-oxo-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d][8]annulene-4-carbaldehyde
InChIKey: PLWMYIADTRHIMY-BNFAVABNSA-N
SMILES: O=C/C1=C/C[C@]([C@@H]([C@@H](C)CC/C=C(C)\C)CC2)([H])[C@@]2(C)C[C@@]([C@](C)(O)C3)([H])[C@]1([H])C3=O
Biological Activity: Ophiobolin C inhibits CCR5 binding to the envelop protein gp120 and CD4, which is responsible for mediating the entry of HIV-1 into cells[1]. Ophiobolin C is also cytotoxic to chronic lymphocytic leukemia cells[2].
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Ophiobolin C | Ophiobolin C inhibits CCR5 binding to the envelop protein gp120 and CD4, which is responsible for mediating the entry of HIV-1 into cells. Ophiobolin C is also cytotoxic to chronic lymphocytic leukemia cells. | |||||||||||||||||||||
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References
- [1]. Jayasuriya H, et al. Isolation and structure of antagonists of chemokine receptor (CCR5). J Nat Prod. 2004 Jun;67(6):1036-8. [Content Brief]
- [2]. Bladt TT, et al. Bio-activity and dereplication-based discovery of ophiobolins and other fungal secondary metabolites targeting leukemia cells. Molecules. 2013 Nov 26;18(12):14629-50. [Content Brief]
