A calmodulin antagonist
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Ophiobolin A

Item No. 15381

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2'S,3'S,3aR,5'R,6aS,9R,9aS,10aR)-1,3a,4,4',5',6a,7,8,9,9a,10,10a-dodecahydro-9-hydroxy-3',9,10a-trimethyl-5'-spiro[dicyclopenta[a,d]cyclooctene-3(2H),2'(3'H)-furan]-6-carboxaldehyde
CAS Number
4611-05-6
Synonyms
  • Cochliobolin
  • NSC 114340
Molecular Formula
C25H36O4
Formula Weight
400.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
C[C@H]1C[C@@H](O[C@]12[C@]3([H])C/C=C([C@]([H])([C@]([H])(C[C@]3(CC2)C)[C@](C4)(C)O)C4=O)/C([H])=O)/C=C(C)\C
InChi Code
InChI=1S/C25H36O4/c1-15(2)10-18-11-16(3)25(29-18)9-8-23(4)12-19-22(20(27)13-24(19,5)28)17(14-26)6-7-21(23)25/h6,10,14,16,18-19,21-22,28H,7-9,11-13H2,1-5H3/b17-6-/t16-,18-,19-,21+,22+,23+,24+,25-/m0/s1
InChi Key
MWYYLZRWWNBROW-BDZRSQQBSA-N
Origin
Fungus/Bipolaris leersia
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $303

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    5 mg

    $902

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    Product Description

    Calmodulin is a calcium-sensing protein that regulates a wide array of proteins involved in diverse cellular functions.1,2 Ophiobolin A is a sesterterpenoid fungal phytotoxin that binds and irreversibly antagonizes calmodulin, blocking the activation of calmodulin-dependent phosphodiesterase with an IC50 value of 9 μM.3 It antagonizes a variety of forms of calmodulin from plants and animals by binding covalently to conserved lysine residues.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chin, D., and Means, A.R. Calmodulin: A prototypical calcium sensor. Trends Cell Biol. 10(8), 322-328 (2000).

    2. Berchtold, M.W., and Villalobo, A. The many faces of calmodulin in cell proliferation, programmed cell death, autophagy, and cancer. Biochim. Biophys. Acta 1843(2), 398-435 (2014).

    3. Leung, P.C., Taylor, W.A., Wang, J.H., et al. Ophiobolin A. A natural product inhibitor of calmodulin. The Journal of Biological Chemisty 259(5), 2742-2747 (1984).

    4. Au, T.K., and Leung, P.C. Identification of the binding and inhibition sites in the calmodulin molecule for ophiobolin A by site-directed mutagenesis. Plant Physiol. 118(3), 965-973 (1998).

    5. Leung, P.C., Taylor, W.A., Wang, J.H., et al. Role of calmodulin inhibition in the mode of action of ophiobolin A. Plant Physiol. 77(2), 303-308 (1985).