Citreoviridin A (CHEM002706)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (15)XML
Record Information
Version1.0
Creation Date2010-05-06 14:52:05 UTC
Update Date2026-04-03 05:06:40 UTC
Accession NumberCHEM002706
Identification
Common NameCitreoviridin A
ClassSmall Molecule
DescriptionCitreoviridin A is a metabolite of Penicillium citreo-viride, Penicillium toxicarium, Penicillium ochrosalmoneum and Aspergillus terreus. It is isolated from mouldy rice. Toxin formerly responsible for epidemic-like occurrences of cardiac beriberi in East Asia Citreoviridin A belongs to the family of Pyranones and Derivatives. These are compounds containing a pyran ring which bears a ketone.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC23H30O6
Average Molecular Mass402.481 g/mol
Monoisotopic Mass402.204 g/mol
CAS Registry Number25425-12-1
IUPAC Name6-[(1E,3E,5E,7E)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methyl-2H-pyran-2-one
Traditional Name6-[(1E,3E,5E,7E)-8-(3,4-dihydroxy-2,4,5-trimethyloxolan-2-yl)-7-methylocta-1,3,5,7-tetraen-1-yl]-4-methoxy-5-methylpyran-2-one
SMILES[H]/C(=C(/[H])\C(\[H])=C(/[H])C1=C(C)C(OC)=CC(=O)O1)/C(/[H])=C(\[H])/C(/C)=C(\[H])C1(C)OC(C)C(C)(O)C1O
InChI IdentifierInChI=1S/C23H30O6/c1-15(14-22(4)21(25)23(5,26)17(3)29-22)11-9-7-8-10-12-18-16(2)19(27-6)13-20(24)28-18/h7-14,17,21,25-26H,1-6H3/b8-7+,11-9+,12-10+,15-14+
InChI KeyJLSVDPQAIKFBTO-USJRQALFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentPyranones and derivatives
Alternative Parents
Substituents
  • Alkyl aryl ether
  • Pyranone
  • Heteroaromatic compound
  • Vinylogous ester
  • Tetrahydrofuran
  • Tertiary alcohol
  • 1,2-diol
  • Lactone
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Point107 - 111°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0094 g/LALOGPS
logP3.89ALOGPS
logP2.46ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.6ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity118.01 m³·mol⁻¹ChemAxon
Polarizability45.46 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-0udi-0397800000-0f9771cfe7cb0f49d20bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfs-0693100000-23553164c96a08dc9889Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9730000000-6504eb2eeea870dfbee4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2116900000-70772f3c9c6f3fd5a55cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-6309400000-71c410220beebeb86e26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006y-9243000000-cf75b7ceb40a5bbec180Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (7)
Mechanism of ToxicityCitreoviridin inhibits both membrane-bound and soluble mitochondrial ATPases. In particular, it inhibits synaptosomal Na+/K+-ATPase, altering synaptic transmission, and binds to the beta subunit of F1-ATPAse. As a result it has been shown to inhibit mitochondrial energy-linked reactions such as ADP-stimulated respiration, ATP-driven reduction of NAD + by succinate, and ATP-driven NAD transhydrogenase. 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, interfering 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, 6)
MetabolismNot Available
Toxicity ValuesLD50: 3.6 mg/kg (Subcutaneous, rat) (1) LD50: 7.5 mg/kg (Intraperitoneal, Mouse) (1) LD50: 29 mg/kg (Oral, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCitreoviridin is a mycotoxin that has been isolated in Peniciilium citreo-viride, P. ochrosalmoneum, and P. pulvullorum. It can be found in contaminated rice grains, as well as corn infested by Eupenicillium ochrosalmoneurn. (1)
Minimum Risk LevelNot Available
Health EffectsCitreoviridin selectively inhibits motor nerve cells in the medulla oblongata and accumulates in the grey matter and brain stem. This can cause central nervous system depression leading to respiratory and cardiovascular failures and death. (1, 3, 4)
SymptomsSymptoms of citreoviridin exposure include progressive paralysis, vomiting, convulsions, and gradual respiratory disorder. (1)
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 LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5375783
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available