Cyclopiazonic acid (CHEM002705)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (9)XML
Record Information
Version1.0
Creation Date2010-05-05 19:41:24 UTC
Update Date2026-04-03 05:06:43 UTC
Accession NumberCHEM002705
Identification
Common NameCyclopiazonic acid
ClassSmall Molecule
DescriptionCyclopiazonic acid (CPA) is a myxotoxin originally isolated from Penicillium cyclopium and subsequently from Penicillium griseofulvum, Penicillium camembertii, Aspergillus flavus and Aspergillus versicolor. It is often found co-occurring with aflatoxins. CPA is a natural contaminant of corn, peanuts, and sunflowers, as well as various types of cheese, sausages, and salamis. It may also occur in eggs, milk and meats from animal that have consumed CPA-contaminated feed and is toxic in high concentrations. (7, 2)
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Food Toxin
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CyclopiazonateGenerator
Chemical FormulaC20H20N2O3
Average Molecular Mass336.384 g/mol
Monoisotopic Mass336.147 g/mol
CAS Registry Number18172-33-3
IUPAC Name5-acetyl-6-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),5,11(18),12,14-pentaen-4-one
Traditional Name5-acetyl-6-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),5,11(18),12,14-pentaen-4-one
SMILESCC(=O)C1=C(O)N2C(C3C(CC4=C5C(NC=C35)=CC=C4)C2(C)C)C1=O
InChI IdentifierInChI=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/h4-6,8,12,16-17,21,25H,7H2,1-3H3
InChI KeyRLOAZVAJNNPPDI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Isoindole or derivatives
  • Isoindoline
  • Pyrrolizine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Vinylogous acid
  • Pyrroline
  • Pyrrolidine
  • Pyrrole
  • Ketone
  • Ketene acetal or derivatives
  • Azacycle
  • Alkanolamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.47ALOGPS
logP3.08ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.56ChemAxon
pKa (Strongest Basic)2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area73.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity104 m³·mol⁻¹ChemAxon
Polarizability36.22 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0049000000-beed7ad8d422dddd235eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-0139000000-74b4d3a12818ba276b0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0930000000-0c3b3885c6f053326fc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-0069000000-f82fe95bc7b5e0693f15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1091000000-c68a07a4a2e1691b83c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0600-9180000000-429a3089cb5b2f2add85Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (6)
Mechanism of ToxicityCyclopiazonic acid is potent and specific inhibitor of the endoplasmic and sarcoplasmic reticulum Ca+-dependent ATPases, which are essential for calcium reuptake in the muscle contraction-relaxation cycle. CPA blocks the calcium access channel and rigidifies a subset of transmembrane helices in a nonnative configuration that is incompatible with calcium binding. Inhibition of Ca2+-ATPases results in cell death through the activation of stress-response and apoptotic pathways within the endoplasmic reticulum and mitochondria. CPA can also induce both secretion and mRNA levels of proinflammatory cytokines, likely leading to macrophage activation and immunotoxic effects. In addition, it has been shown to be mutagenic and genotoxic. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (1, 2, 4, 5)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseLD50: 13 mg/kg (Intraperitoneal, Mouse) (3) LD50: 2.3 mg/kg (Intraperitoneal, Rat) (4)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCyclopiazonic acid (CPA) is a myxotoxin originally isolated from Penicillium cyclopium and subsequently from Penicillium griseofulvum, Penicillium camembertii, Aspergillus flavus and Aspergillus versicolor. It is often found co-occurring with aflatoxins. CPA is a natural contaminant of corn, peanuts, and sunflowers, as well as various types of cheese, sausages, and salamis. It may also occur in eggs, milk and meats from animal that have consumed CPA-contaminated feed. (7, 2)
Minimum Risk LevelNot Available
Health EffectsCyclopiazonic acid affects muscle function and may also be immunotoxic, genotoxic, and mutagenic. (2, 3, 4)
SymptomsAnimals studies have shown cyclopiazonic acid to cause symptoms such as tremors, convulsions, dyspnoea, hypokinesia, hypothermia, sedation, tachycardia, and tachypnoea. (3)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCyclopiazonic acid
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID2908
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available