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Structure Database (LMSD)

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Common Name

Ophiobolin A

Systematic Name

Synonyms

LM ID

LMPR0105050001

Formula

C₂₅H₃₆O₄

Exact Mass

Calculate m/z

400.261361

Status

Curated

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Classification

Biological Context

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

This information has been provided by Cayman Chemical

References

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

2. 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).

3. 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).

4. 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).

5. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Bipolaris gigantea (#2695822)

Dothideomycetes (#147541)

Ophiobolin A,
Acta Cryst E, 2006

DOI: 10.1107/S1600536806015807

String Representations

InChiKey (Click to copy)

MWYYLZRWWNBROW-BDZRSQQBSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@]12(CC[C@]3(C)C[C@]4([H])[C@@](O)(C)CC(=O)[C@]4([H])C(C=O)=CC[C@@]13[H])[C@@H](C)C[C@H](/C=C(\C)/C)O2