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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:11 UTC
Update Date2018-03-12 21:59:43 UTC
HMDB IDHMDB0029399
Secondary Accession Numbers
  • HMDB29399
Metabolite Identification
Common NameOchratoxin A
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
Structure
Thumb
Synonyms
ValueSource
(R)-N-((5-chloro-3,4-dihydro-8-Hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)phenylalanineChEBI
Antibiotic 9663HMDB
N-[(5-chloro-3,4-dihydro-8-Hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl]phenylalanine, 9ciHMDB
Ochratoxin a-bsa conjugate from aspergillus ochraceusHMDB
OTAHMDB
Phenylalanine - ochratoxin aHMDB
Chemical FormulaC20H18ClNO6
Average Molecular Weight403.813
Monoisotopic Molecular Weight403.08226502
IUPAC Name(2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-phenylpropanoic acid
Traditional Nameochratoxin A
CAS Registry Number303-47-9
SMILES
C[C@@H]1CC2=C(C(=O)O1)C(O)=C(C=C2Cl)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=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)/t10-,15+/m1/s1
InChI KeyRWQKHEORZBHNRI-BMIGLBTASA-N
Chemical Taxonomy
DescriptionThis compound 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
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • 3-phenylpropanoic-acid
  • 2-benzopyran
  • 3-halobenzoic acid or derivatives
  • Salicylic acid or derivatives
  • Isochromane
  • Benzopyran
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Benzamide
  • 4-halophenol
  • Benzoyl
  • Chlorobenzene
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Vinylogous acid
  • Secondary carboxylic acid amide
  • Lactone
  • Carboxylic acid ester
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point169 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.74Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP3.18ALOGPS
logP4.61ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.93 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.77 m³·mol⁻¹ChemAxon
Polarizability40.12 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9346000000-0f256a6b22cf7bb2e294View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-9210330000-961847cfb020199e91a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9i-4139700000-7370054788c4ba422c78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2279000000-db0e6b9748bb326f459bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9520000000-1ef633b0c26d3fb20ae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0009400000-edc4f177319e57616957View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-2539200000-3b92a4651b761437b140View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9221000000-a1d42d3201899ff492f0View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000488
KNApSAcK IDC00003008
Chemspider ID390954
KEGG Compound IDC09955
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442530
PDB IDNot Available
ChEBI ID7719
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .