Ochratoxin C (CHEM002583)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-11-13 22:52:25 UTC
Update Date2026-04-06 10:37:36 UTC
Accession NumberCHEM002583
Identification
Common NameOchratoxin C
ClassSmall Molecule
DescriptionOchratoxin C is a metabolite of Aspergillus ochraceus Ochratoxin C 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
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
  • Organochloride
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Ochratoxin a ethyl esterHMDB
5-Chloro-N-(1-ethoxy-1-oxo-3-phenylpropan-2-yl)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboximidateHMDB
Chemical FormulaC22H22ClNO6
Average Molecular Mass431.866 g/mol
Monoisotopic Mass431.114 g/mol
CAS Registry Number4865-85-4
IUPAC Name5-chloro-N-(1-ethoxy-1-oxo-3-phenylpropan-2-yl)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboximidic acid
Traditional Name5-chloro-N-(1-ethoxy-1-oxo-3-phenylpropan-2-yl)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-carboximidic acid
SMILESCCOC(=O)C(CC1=CC=CC=C1)N=C(O)C1=CC(Cl)=C2CC(C)OC(=O)C2=C1O
InChI IdentifierInChI=1S/C22H22ClNO6/c1-3-29-21(27)17(10-13-7-5-4-6-8-13)24-20(26)15-11-16(23)14-9-12(2)30-22(28)18(14)19(15)25/h4-8,11-12,17,25H,3,9-10H2,1-2H3,(H,24,26)
InChI KeyBPZZWRPHVVDAPT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • Hexose monosaccharide
  • N-glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Aralkylamine
  • Monosaccharide
  • Oxane
  • Azole
  • Heteroaromatic compound
  • Isoxazole
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Primary aliphatic amine
  • Primary amine
  • Organonitrogen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • 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 PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.96ALOGPS
logP5.93ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.42 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity111.81 m³·mol⁻¹ChemAxon
Polarizability43.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4019000000-d2a641a855118404e3bcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03fu-9002260000-31b2f835982ccd442d9fSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-4212900000-efe849f14e9d887fdfa1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-4397400000-e2938a4d4ece4b5ee369Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9210000000-46647db7246af80a6e10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2019500000-0e6b84dd14ef1152c403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-6469400000-2b606454b44f5e5551c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9111000000-78fb701981189e5cacd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-7ea3cfffa1f605d198dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f7o-4935800000-9f550c61aeec7cbd7cf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-4491000000-f6cb7f8400d2bc6255b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0004900000-4bdf05cff8a50f221350Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5l-2593300000-926aecf8ff2fc365bdcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-8950000000-00fa22804f8981975e62Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (5)
Mechanism of ToxicityOchratoxin A, a metabolite of Ochratoxin C, 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. (2)
MetabolismIt is concluded that ochratoxin C is readily converted to ochratoxin A after both oral and intravenous administration. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
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. (6)
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; might delay sexual maturation. (1)
SymptomsMight cause respiratory irritation. (1)
TreatmentCare is symptomatic and supportive. (1)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029400
FooDB IDFDB000489
Phenol Explorer IDNot Available
KNApSAcK IDC00057404
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID536626
ChEBI IDNot Available
PubChem Compound ID617474
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.