Cyclopiazonic acid

• CAT Number: M083242
• CAS Number: 18172-33-3
• Molecular Formula: C20H20N2O3
• Molecular Weight: 336.38
• Purity: ≥95%
• Synonyms: (2R,3S,5E,9R)-5-(1-hydroxyethylidene)-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.02,9.03,7.015,18]octadeca-1(17),11(18),12,14-tetraene-4,6-dione
• IUPAC Name: (2R,3S,5Z,9R)-5-(1-hydroxyethylidene)-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.02,9.03,7.015,18]octadeca-1(17),11(18),12,14-tetraene-4,6-dione
• 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/h4-6,8,12,16-17,21,23H,7H2,1-3H3/b14-9-/t12-,16+,17+/m1/s1
• InChIKey: CNZIQHGDUXRUJS-PTNHGACKSA-N
• SMILES: C/C(=C/1\C(=O)[C@@H]2[C@@H]3[C@@H](CC4=C5C3=CNC5=CC=C4)C(N2C1=O)(C)C)/O

Cyclopiazonic acid (Cat No.:M083242) is a mycotoxin produced by certain strains of Aspergillus and Penicillium species. Structurally classified as an indole-tetramic acid, CPA is known for its potent inhibition of sarcoplasmic and endoplasmic reticulum Ca²⁺-ATPases (SERCA), disrupting calcium homeostasis in cells. It is commonly studied in toxicology, food safety, and cellular signaling research due to its neurotoxic and cytotoxic effects. Cyclopiazonic acid is of concern in contaminated agricultural products, particularly grains and cheeses, and serves as a useful tool in studying calcium-regulated physiological and pathological processes.

Reference

[1]. Chalivendra SC, et al. Cyclopiazonic Acid Is a Pathogenicity Factor for Aspergillus flavus and a Promising Target for Screening Germplasm for Ear Rot Resistance. Mol Plant Microbe Interact. 2017 May;30(5):361-373.
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