Cyclopiazonic acid

Cyclopiazonic acid: Cyclopiazonic acid

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 number 18172-33-3^N

PubChem 65261

ChemSpider 21106432^Y

ChEBI CHEBI:22450^Y

ChEMBL CHEMBL480627^Y

Jmol-3D images Image 1

SMILES

CC(=O)/C1=C(\O)[C@H]5N(C1=O)[C@@](C)(C)[C@@H]4Cc2cccc3ncc(c23)[C@@H]45

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

Properties

Molecular formula C₂₀H₂₀N₂O₃

Molar mass 336.38 g mol⁻¹

N acid (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Cyclopiazonic acid (CPA) is a toxic fungal secondary metabolite. Chemically, it is an indole tetramic acid.

CPA was originally isolated from Penicillium cyclopium and subsequently from other P. cyclopium, Penicillium griseofulvum, Penicillium camembertii, Aspergillus flavus and Aspergillus versicolor.

Cyclopiazonic acid only appears to be toxic in high concentrations.

Biologically, Cyclopiazonic acid is a specific inhibitor of Ca²⁺-ATPase in the intracellular Ca²⁺ storage sites.

Categories:
Mycotoxins
Indoles
Alcohols
Ketones
Lactams

Cyclopiazonic acid

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 number	18172-33-3^N
PubChem	65261
ChemSpider	21106432^Y
ChEBI	CHEBI:22450^Y
ChEMBL	CHEMBL480627^Y
Jmol-3D images	Image 1
SMILES CC(=O)/C1=C(\O)[C@H]5N(C1=O)[C@@](C)(C)[C@@H]4Cc2cccc3ncc(c23)[C@@H]45
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
Properties
Molecular formula	C₂₀H₂₀N₂O₃
Molar mass	336.38 g mol⁻¹
N acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Look at other dictionaries:

cyclopiazonic acid — noun A polycyclic metabolite of the fungus Penicillium cyclopium that interferes with calcium metabolism … Wiktionary
cyclopiazonic — adjective Of or pertaining to cyclopiazonic acid or its derivatives … Wiktionary
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Food microbiology — is the study of the microorganisms which inhabit, create or contaminate food. Of major importance is the study of microorganisms causing food spoilage.cite book | author = Fratamico PM and Bayles DO (editor). | title = Foodborne Pathogens:… … Wikipedia
CPA — Canadian Physiotherapy Association; Canadian Psychiatric Association; carboxypeptidase A; cardiophrenic angle; cardiopulmonary arrest; carotid phonoan giography; cerebellopontine angle; child physical abuse; chlorophenoxyacetic acid;… … Medical dictionary
CPA — • Canadian Physiotherapy Association; • Canadian Psychiatric Association; • carboxypeptidase A; • cardiophrenic angle; • cardiopulmonary arrest; • carotid phonoan giography; • cerebellopontine angle; • child physical abuse; • chlorophenoxyacetic… … Dictionary of medical acronyms & abbreviations

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Cyclopiazonic acid

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