Ochratoxin B (T3D3606)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-11-13 22:46:58 UTC
Update Date2014-12-24 20:26:13 UTC
Accession NumberT3D3606
Identification
Common NameOchratoxin B
ClassSmall Molecule
DescriptionOchratoxin B is a metabolite of Aspergillus ochraceus Ochratoxin B 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).
Compound Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-[(8-Hydroxy-3-methyl-1-oxoisochroman-7-carbonyl)amino]-3-phenylpropionic acid
N-[(8-Hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl)carbonyl]phenylalanine
Chemical FormulaC20H19NO6
Average Molecular Mass369.368 g/mol
Monoisotopic Mass369.121 g/mol
CAS Registry Number4825-86-9
IUPAC Name2-{[hydroxy(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)methylidene]amino}-3-phenylpropanoic acid
Traditional Name2-{[hydroxy(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)methylidene]amino}-3-phenylpropanoic acid
SMILESCC1CC2=C(C(=O)O1)C(O)=C(C=C2)C(O)=NC(CC1=CC=CC=C1)C(O)=O
InChI IdentifierInChI=1/C20H19NO6/c1-11-9-13-7-8-14(17(22)16(13)20(26)27-11)18(23)21-15(19(24)25)10-12-5-3-2-4-6-12/h2-8,11,15,22H,9-10H2,1H3,(H,21,23)(H,24,25)
InChI KeyInChIKey=DAEYIVCTQUFNTM-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ochratoxins and related substances. These are a group of chemically related metabolites containing a 3,4-dihydro-3-methylisocoumarin moiety linked through a carboxyl group to L-beta-phenylalanine by a secondary amine bond.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassOchratoxins and related substances
Sub ClassNot Available
Direct ParentOchratoxins and related substances
Alternative Parents
Substituents
  • Ochratoxin-skeleton
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Salicylic acid or derivatives
  • 2-benzopyran
  • Isochromane
  • Benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Lactone
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Carboxylic acid
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • 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
AppearanceCrystals from methanol. (4)
Experimental Properties
PropertyValue
Melting Point221°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.067 g/LALOGPS
logP2.89ALOGPS
logP4.83ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
pKa (Strongest Basic)0.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area116.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.49 m³·mol⁻¹ChemAxon
Polarizability37.01 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9188000000-465239f3bd78eb30bd632017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-6012890000-f11d1dffcd9b915bacf92017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-2219000000-50c4b901f9dd1f436db42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fu-2597000000-1f43b9bf5e9f0cb801172016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-0ea895a91c60938f82172016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0029000000-8b9a1400d7de1b8460f52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0100-2669000000-b399dc5e8324895bef282016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6930000000-95579f686cf729c65a222016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gi0-0829000000-8c84a51e9e11593d1cd52021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gi4-3849000000-6305fce231bb3e0b71bc2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ugl-3940000000-d7838720f0f845c19ee72021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-c8e6150e81e908b0971e2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l6r-0946000000-c51245f8d3561a8a0bd02021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fml-1920000000-ad9d01b16eda880f5d9b2021-09-24View Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (3)
Mechanism of ToxicityOchratoxin B is thought to inhibit the accumulation of cartilage proteoglycans and general protein synthesis in a concentration-related manner. (2)
MetabolismOchratoxin B is metabolized to 4-hydroxyochratoxin B. (1)
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. (9)
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. (5)
SymptomsMight cause respiratory irritation. (5)
TreatmentCare is symptomatic and supportive. (5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB29401
PubChem Compound ID609663
ChEMBL IDNot Available
ChemSpider ID529965
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3606.pdf
General References
  1. Stormer FC, Kolsaker P, Holm H, Rogstad S, Elling F: Metabolism of ochratoxin B and its possible effects upon the metabolism and toxicity of ochratoxin A in rats. Appl Environ Microbiol. 1985 May;49(5):1108-12. [4004232 ]
  2. Wiger R, Stormer FC: Effects of ochratoxins A and B on prechondrogenic mesenchymal cells from chick embryo limb buds. Toxicol Lett. 1990 Dec;54(2-3):129-34. [2260111 ]
  3. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  4. Rothenberg SP, Marcoullis GP, Schwarz S, Lader E: Measurement of cyanocobalamin in serum by a specific radioimmunoassay. J Lab Clin Med. 1984 Jun;103(6):959-72. [6726060 ]
  5. Grond S, Sablotzki A: Clinical pharmacology of tramadol. Clin Pharmacokinet. 2004;43(13):879-923. [15509185 ]
  6. Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. Hall AH & Rumack BH (Eds): TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010.
  7. O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1209
  8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  9. Wikipedia. Ochratoxin A. Last Updated 26 February 2010. [Link]
  10. Wikipedia. Ochratoxin. Last Updated 29 March 2010. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available