Cyclopiazonic acid

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Cyclopiazonic acid
Cyclopiazonic acid.svg
CAS number 18172-33-3 N
PubChem 65261
ChemSpider 21106432 YesY
ChEBI CHEBI:22450 YesY
Jmol-3D images Image 1
Molecular formula C20H20N2O3
Molar mass 336.38 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Cyclopiazonic acid (CPA) is a toxic fungal secondary metabolite.[1] Chemically, it is an indole tetramic acid. CPA was originally isolated from Penicillium cyclopium and subsequently from other fungi including Penicillium griseofulvum, Penicillium camemberti, Aspergillus flavus, and Aspergillus versicolor. CPA only appears to be toxic in high concentrations. Biologically, CPA is a specific inhibitor of Ca2+-ATPase in the intracellular Ca2+ storage sites.


  1. ^ Holzapfel, C. W. (1968). "The isolation and structure of cyclopiazonic acid, a toxic metabolite of Penicillium cyclopium Westling". Tetrahedron 24 (5): 2101–2119. doi:10.1016/0040-4020(68)88113-X. PMID 5636916.