An antiviral phytotoxin
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Isomer(s)
40937Ophiobolin H
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Ophiobolin C

Item No. 20186

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3aS,6aS,7R,9aR,10aS)-7-[(1S)-1,5-dimethyl-4-hexen-1-yl]-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-1-hydroxy-1,9a-dimethyl-3-oxo-dicyclopenta[a,d]cyclooctene-4-carboxaldehyde
CAS Number
19022-51-6
Molecular Formula
C25H38O3
Formula Weight
386.6
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
λmax
238 nm
SMILES
C[C@@]12C[C@@]([H])([C@]3(/C(C=O)=C\C[C@]1([C@]([H])(CC2)[C@H](CC/C=C(C)\C)C)[H])[H])[C@](CC3=O)(C)O
InChi Code
InChI=1S/C25H38O3/c1-16(2)7-6-8-17(3)19-11-12-24(4)13-21-23(22(27)14-25(21,5)28)18(15-26)9-10-20(19)24/h7,9,15,17,19-21,23,28H,6,8,10-14H2,1-5H3/b18-9-/t17-,19+,20-,21-,23+,24+,25+/m0/s1
InChi Key
PLWMYIADTRHIMY-BNFAVABNSA-N
Origin
Fungus/Bipolaris sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $306

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    5 mg

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    Product Description

    Ophiobolin C is a sesterterpenoid fungal phytoxin produced by many species of the genus Bipolaris. It has been identified as an antagonist of chemokine receptor CCR5 binding (IC50 = 40 µM) to the envelope protein gp120 and to CD4, which is known to mediate HIV-1 viral entry into cells.1 Ophiobolin C is also reported to be cytotoxic to chronic lymphocytic leukemia cells (LC50 = 8 nM).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jayasurla, H., Herath, K.B., Ondeyka, J.G., et al. Isolation and structure of antagonists of chemokine receptor (CCR5). J. Nat. Prod. 67(6), 1036-1038 (2004).

    2. Bladt, T.T., Dürr, C., Knudsen, P.B., et al. Bio-activity and dereplication-based discovery of ophiobolins and other fungal secondary metabolites targeting leukemia cells. Molecules 18(12), 14629-14650 (2013).