Ochratoxin A (CHEM002581)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-11-13 22:25:18 UTC
Update Date2026-03-26 20:59:06 UTC
Accession NumberCHEM002581
Identification
Common NameOchratoxin A
ClassSmall Molecule
DescriptionOchratoxin A is found in barley. Mycotoxin. Ochratoxin A is produced by Aspergillus melleus, Aspergillus sulphureus and Penicillium viridicatum.Potential contaminant of foodstuffs, especially cereals. Ochratoxin A is found in stored grain products in UK (1997).Ochratoxin A, a toxin produced by Aspergillus ochraceus and Penicillium verrucosum, is one of the most abundant food-contaminating mycotoxins in the world. Human exposure occurs mainly through consumption of improperly stored food products, particularly contaminated grain and pork products, as well as coffee, wine grapes and dried grapes. The toxin has been found in the tissues and organs of animals, including human blood and breast milk. Ochratoxin A toxicity has large species- and sex-specific differences. Ochratoxin a belongs to the family of Ochratoxins and related substances. These are compounds containing the ochratoxin skeleton, which is structurally characterized by the presence of a 3-phenylpropanoic acid N-linked to a 8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxamide moiety[1]. (Reference: [1] http://www.inchem.org/documents/ehc/ehc/ehc105.htm).
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
  • Organochloride
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC20H18ClNO6
Average Molecular Mass403.813 g/mol
Monoisotopic Mass403.082 g/mol
CAS Registry Number303-47-9
IUPAC Name2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid
Traditional Name2-{[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)(hydroxy)methylidene]amino}-3-phenylpropanoic acid
SMILESCC1CC2=C(Cl)C=C(C(O)=NC(CC3=CC=CC=C3)C(O)=O)C(O)=C2C(=O)O1
InChI IdentifierInChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)
InChI KeyRWQKHEORZBHNRI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Carboxylic acid anhydride
  • Primary carboxylic acid amide
  • Carboxamide group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceCrystals from xylene. Exhibits green fluorescence. (2)
Experimental Properties
PropertyValue
Melting Point169°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP3.66ALOGPS
logP5.43ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.26ChemAxon
pKa (Strongest Basic)0.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity102.29 m³·mol⁻¹ChemAxon
Polarizability39.19 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8029000000-d1bf01a02fb90e9a4b65Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000l-0490000000-9a04e8c0462d1c96809bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0094000000-c2ab0c40cb596b683899Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4r-0090000000-546b30ed135b3b25ddefSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052u-0090000000-2068ef10c89919fbfb5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0094000000-2d6cba74ee0469c26202Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0014900000-467d3c8ff084d3ddb7f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000l-0490000000-5b15816e701a6cdedad7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-5328900000-bb6ff8935be11e6eba85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053l-2259000000-f59d898f61dc363b9df8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9410000000-3d2f33580d5bdfc5b412Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0019500000-d12f604ac4aad770e948Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114i-1449200000-49a8c330112595e2a6a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-9315be65c28edeb93241Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0014900000-281f3e41572a5688329bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0493100000-5ff60809a74a8f9eccebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ukc-1940000000-3adbd5dc0d55a73549c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0307900000-6789ab041535acae6b8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-7895200000-9cc414002f922433d1b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsu-5790000000-ff412cab49c6facab300Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (8)
Mechanism of ToxicityOchratoxin A has been shown to be weakly mutagenic, possibly by induction of oxidative DNA damage. The nephrotoxin ochratoxin A (OTA) causes a reduction of glomerular filtration rate (GFR) and of para-aminohippuric acid (PAH) clearance. It is a nephrotoxin which blocks plasma membrane anion conductance in Madin-Darby canine kidney (MDCK) cells. Some cytochrome P-450 enzymes, such as CYP2C9, are known to metabolize ochratoxin A into more cytotoxic compounds capable of forming DNA adducts. (4, 7)
MetabolismOchratoxin A is cleaved into phenylalanine and a less toxic iso-coumarin derivative (ochratoxin alpha) by the microbial flora of the colon, and by carboxypeptidase A and alpha-chymotrypsim. This is is the major metabolic pathway. 4-Hydroxyochratoxin A is the main hepatic metabolite and its formation appears to be via a polymorphic-like debrisoquine 4-hydroxylation. Some cytochrome P-450 enzymes, such as CYP2C9, and known to metabolize ochratoxin A into more cytotoxic compounds. (11, 5, 7)
Toxicity ValuesLD50: 20 mg/kg (Oral, Rat) (3) LD50: 12,600 ug/kg (Intraperitoneal, Rat) (3) LD50: 12,750 ug/kg (Intravenous, Rat ) (3) LD50: 46 mg/kg (Oral, Mouse) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (9)
Uses/SourcesHuman exposure occurs mainly through consumption of improperly stored food products, particularly contaminated grain and pork products, as well as coffee, wine grapes and dried grapes. (10)
Minimum Risk LevelNot Available
Health EffectsOchratoxin exposure has been associated with acute tubular necrosis and Balkan endemic nephropathy. Ochratoxin A has been shown to be nephrotoxic and might delay sexual maturation. It can cause immunosuppression and immunotoxicity in animals. It's immunosuppressant activity in animals may include depressed antibody responses, reduced size of immune organs (such as the thymus, spleen, and lymph nodes), changes in immune cell number and function, and altered cytokine production. Immunotoxicity probably results from cell death following apoptosis and necrosis, in combination with slow replacement of affected immune cells due to inhibition of protein synthesis. (1, 10)
SymptomsMight cause respiratory irritation. (1)
TreatmentCare is symptomatic and supportive. (1)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0256434
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003008
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOchratoxin A
Chemspider ID4419
ChEBI IDNot Available
PubChem Compound ID4580
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General ReferencesNot Available