A calmodulin antagonist
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

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
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
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $303

    Add

    5 mg

    $902

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    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).