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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:11 UTC
Update Date2022-03-07 02:52:09 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
Data?1582753413
Synonyms
ValueSource
(2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoic acidChEBI
(R)-N-((5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)phenylalanineChEBI
N-[(3R)-5-Chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-L-phenylalanineChEBI
N-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]carbonyl}-L-phenylalanineChEBI
OTAChEBI
(2S)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoateGenerator
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
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
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 or derivatives
  • N-acyl-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Salicylic acid or derivatives
  • 2-benzopyran
  • Isochromane
  • Benzopyran
  • Aryl halide
  • Benzenoid
  • Aryl chloride
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Lactone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point169 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.99 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.74Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+188.07330932474
DeepCCS[M-H]-185.67830932474
DeepCCS[M-2H]-218.92230932474
DeepCCS[M+Na]+193.98630932474
AllCCS[M+H]+192.132859911
AllCCS[M+H-H2O]+189.532859911
AllCCS[M+NH4]+194.432859911
AllCCS[M+Na]+195.132859911
AllCCS[M-H]-190.732859911
AllCCS[M+Na-2H]-190.832859911
AllCCS[M+HCOO]-190.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ochratoxin AC[C@@H]1CC2=C(C(=O)O1)C(O)=C(C=C2Cl)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O4695.2Standard polar33892256
Ochratoxin AC[C@@H]1CC2=C(C(=O)O1)C(O)=C(C=C2Cl)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O2965.0Standard non polar33892256
Ochratoxin AC[C@@H]1CC2=C(C(=O)O1)C(O)=C(C=C2Cl)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O3492.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ochratoxin A,1TMS,isomer #1C[C@@H]1CC2=C(Cl)C=C(C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O)C(O[Si](C)(C)C)=C2C(=O)O13249.3Semi standard non polar33892256
Ochratoxin A,1TMS,isomer #2C[C@@H]1CC2=C(Cl)C=C(C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C)C(O)=C2C(=O)O13168.9Semi standard non polar33892256
Ochratoxin A,1TMS,isomer #3C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O)[Si](C)(C)C)C(O)=C2C(=O)O13144.6Semi standard non polar33892256
Ochratoxin A,2TMS,isomer #1C[C@@H]1CC2=C(Cl)C=C(C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C2C(=O)O13194.8Semi standard non polar33892256
Ochratoxin A,2TMS,isomer #2C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O)[Si](C)(C)C)C(O[Si](C)(C)C)=C2C(=O)O13142.9Semi standard non polar33892256
Ochratoxin A,2TMS,isomer #3C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C(O)=C2C(=O)O13094.8Semi standard non polar33892256
Ochratoxin A,3TMS,isomer #1C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C(O[Si](C)(C)C)=C2C(=O)O13140.3Semi standard non polar33892256
Ochratoxin A,3TMS,isomer #1C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C)[Si](C)(C)C)C(O[Si](C)(C)C)=C2C(=O)O13099.4Standard non polar33892256
Ochratoxin A,1TBDMS,isomer #1C[C@@H]1CC2=C(Cl)C=C(C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13472.2Semi standard non polar33892256
Ochratoxin A,1TBDMS,isomer #2C[C@@H]1CC2=C(Cl)C=C(C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C(C)(C)C)C(O)=C2C(=O)O13431.3Semi standard non polar33892256
Ochratoxin A,1TBDMS,isomer #3C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O)[Si](C)(C)C(C)(C)C)C(O)=C2C(=O)O13387.9Semi standard non polar33892256
Ochratoxin A,2TBDMS,isomer #1C[C@@H]1CC2=C(Cl)C=C(C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13604.2Semi standard non polar33892256
Ochratoxin A,2TBDMS,isomer #2C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O)[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13581.7Semi standard non polar33892256
Ochratoxin A,2TBDMS,isomer #3C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(O)=C2C(=O)O13555.6Semi standard non polar33892256
Ochratoxin A,3TBDMS,isomer #1C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13714.3Semi standard non polar33892256
Ochratoxin A,3TBDMS,isomer #1C[C@@H]1CC2=C(Cl)C=C(C(=O)N([C@@H](CC3=CC=CC=C3)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13655.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ochratoxin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9346000000-0f256a6b22cf7bb2e2942017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ochratoxin A GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-9210330000-961847cfb020199e91a12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ochratoxin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ochratoxin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 10V, Positive-QTOFsplash10-0k9i-4139700000-7370054788c4ba422c782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 20V, Positive-QTOFsplash10-000i-2279000000-db0e6b9748bb326f459b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 40V, Positive-QTOFsplash10-0006-9520000000-1ef633b0c26d3fb20ae02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 10V, Negative-QTOFsplash10-0pb9-0009400000-edc4f177319e576169572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 20V, Negative-QTOFsplash10-0pb9-2539200000-3b92a4651b761437b1402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 40V, Negative-QTOFsplash10-0006-9221000000-a1d42d3201899ff492f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 10V, Negative-QTOFsplash10-0udi-0223900000-ef4ea8167de3f9ff4fcc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 20V, Negative-QTOFsplash10-0udi-4916300000-56066b94f1e32bc9b9292021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 40V, Negative-QTOFsplash10-0uyi-7690000000-155cbbeca5ed287618e82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 10V, Positive-QTOFsplash10-0udi-0022900000-9fd6866f295ffed72c0a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 20V, Positive-QTOFsplash10-000i-0492200000-5bda2ffac7fded8aa5562021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin A 40V, Positive-QTOFsplash10-0uki-1970000000-3840c9347cddee0a7fbb2021-09-24Wishart LabView Spectrum
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
FooDB IDFDB000488
KNApSAcK IDC00003008
Chemspider ID390954
KEGG Compound IDC09955
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOchratoxin_A
METLIN IDNot Available
PubChem Compound442530
PDB IDNot Available
ChEBI ID7719
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1136941
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.. .