Cyclopiazonic acid

Cyclopiazonic acid
Names

IUPAC name (6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
Identifiers
CAS Registry Number	18172-33-3^N
ChEBI	CHEBI:22450^Y
ChEMBL	ChEMBL480627^Y
ChemSpider	21106432^Y
InChI InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1^Y Key: SZINUGQCTHLQAZ-DQYPLSBCSA-N^Y InChI=1/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1 Key: SZINUGQCTHLQAZ-DQYPLSBCBO
Jmol-3D images	Image
PubChem	65261
SMILES CC(=O)/C1=C(\O)[C@H]5N(C1=O)[C@@](C)(C)[C@@H]4Cc2cccc3ncc(c23)[C@@H]45
Properties
Molecular formula	C₂₀H₂₀N₂O₃
Molar mass	336.38 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/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, Penicillium commune, 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.^[2]

References

↑ 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.
↑ Sosa, M. J.; Córdoba, J. J.; Díaz, C; Rodríguez, M; Bermúdez, E; Asensio, M. A.; Núñez, F (2002). "Production of cyclopiazonic acid by Penicillium commune isolated from dry-cured ham on a meat extract-based substrate". Journal of food protection 65 (6): 988–92. PMID 12092733.