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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:12 UTC
Update Date2022-03-07 02:52:09 UTC
HMDB IDHMDB0029401
Secondary Accession Numbers
  • HMDB29401
Metabolite Identification
Common NameOchratoxin B
DescriptionOchratoxin B 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. Based on a literature review very few articles have been published on Ochratoxin B.
Structure
Data?1582753413
Synonyms
ValueSource
2-{[hydroxy(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)methylidene]amino}-3-phenylpropanoateHMDB
Chemical FormulaC20H19NO6
Average Molecular Weight369.368
Monoisotopic Molecular Weight369.121237345
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
CAS Registry Number4825-86-9
SMILES
CC1CC2=C(C(=O)O1)C(O)=C(C=C2)C(O)=NC(CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/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 KeyDAEYIVCTQUFNTM-UHFFFAOYSA-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
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point221 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.018 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.54131661259
DarkChem[M-H]-186.90831661259
DeepCCS[M+H]+183.9330932474
DeepCCS[M-H]-181.57230932474
DeepCCS[M-2H]-215.59830932474
DeepCCS[M+Na]+190.82630932474
AllCCS[M+H]+188.132859911
AllCCS[M+H-H2O]+185.332859911
AllCCS[M+NH4]+190.732859911
AllCCS[M+Na]+191.532859911
AllCCS[M-H]-187.332859911
AllCCS[M+Na-2H]-187.132859911
AllCCS[M+HCOO]-187.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ochratoxin BCC1CC2=C(C(=O)O1)C(O)=C(C=C2)C(O)=NC(CC1=CC=CC=C1)C(O)=O4186.4Standard polar33892256
Ochratoxin BCC1CC2=C(C(=O)O1)C(O)=C(C=C2)C(O)=NC(CC1=CC=CC=C1)C(O)=O2711.7Standard non polar33892256
Ochratoxin BCC1CC2=C(C(=O)O1)C(O)=C(C=C2)C(O)=NC(CC1=CC=CC=C1)C(O)=O3174.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ochratoxin B,1TMS,isomer #1CC1CC2=CC=C(C(O)=NC(CC3=CC=CC=C3)C(=O)O)C(O[Si](C)(C)C)=C2C(=O)O13055.4Semi standard non polar33892256
Ochratoxin B,1TMS,isomer #2CC1CC2=CC=C(C(=NC(CC3=CC=CC=C3)C(=O)O)O[Si](C)(C)C)C(O)=C2C(=O)O13020.8Semi standard non polar33892256
Ochratoxin B,1TMS,isomer #3CC1CC2=CC=C(C(O)=NC(CC3=CC=CC=C3)C(=O)O[Si](C)(C)C)C(O)=C2C(=O)O13066.9Semi standard non polar33892256
Ochratoxin B,2TMS,isomer #1CC1CC2=CC=C(C(=NC(CC3=CC=CC=C3)C(=O)O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C2C(=O)O12986.6Semi standard non polar33892256
Ochratoxin B,2TMS,isomer #2CC1CC2=CC=C(C(O)=NC(CC3=CC=CC=C3)C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C2C(=O)O13000.7Semi standard non polar33892256
Ochratoxin B,2TMS,isomer #3CC1CC2=CC=C(C(=NC(CC3=CC=CC=C3)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)C(O)=C2C(=O)O12995.1Semi standard non polar33892256
Ochratoxin B,3TMS,isomer #1CC1CC2=CC=C(C(=NC(CC3=CC=CC=C3)C(=O)O[Si](C)(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C2C(=O)O13009.1Semi standard non polar33892256
Ochratoxin B,1TBDMS,isomer #1CC1CC2=CC=C(C(O)=NC(CC3=CC=CC=C3)C(=O)O)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13300.3Semi standard non polar33892256
Ochratoxin B,1TBDMS,isomer #2CC1CC2=CC=C(C(=NC(CC3=CC=CC=C3)C(=O)O)O[Si](C)(C)C(C)(C)C)C(O)=C2C(=O)O13262.6Semi standard non polar33892256
Ochratoxin B,1TBDMS,isomer #3CC1CC2=CC=C(C(O)=NC(CC3=CC=CC=C3)C(=O)O[Si](C)(C)C(C)(C)C)C(O)=C2C(=O)O13306.9Semi standard non polar33892256
Ochratoxin B,2TBDMS,isomer #1CC1CC2=CC=C(C(=NC(CC3=CC=CC=C3)C(=O)O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13377.6Semi standard non polar33892256
Ochratoxin B,2TBDMS,isomer #2CC1CC2=CC=C(C(O)=NC(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)O13412.8Semi standard non polar33892256
Ochratoxin B,2TBDMS,isomer #3CC1CC2=CC=C(C(=NC(CC3=CC=CC=C3)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O)=C2C(=O)O13417.8Semi standard non polar33892256
Ochratoxin B,3TBDMS,isomer #1CC1CC2=CC=C(C(=NC(CC3=CC=CC=C3)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2C(=O)O13542.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ochratoxin B GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9188000000-465239f3bd78eb30bd632017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ochratoxin B GC-MS (3 TMS) - 70eV, Positivesplash10-00di-6012890000-f11d1dffcd9b915bacf92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ochratoxin B 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 B 10V, Positive-QTOFsplash10-00di-2219000000-50c4b901f9dd1f436db42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 20V, Positive-QTOFsplash10-05fu-2597000000-1f43b9bf5e9f0cb801172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 40V, Positive-QTOFsplash10-0006-9400000000-0ea895a91c60938f82172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 10V, Negative-QTOFsplash10-00xr-0029000000-8b9a1400d7de1b8460f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 20V, Negative-QTOFsplash10-0100-2669000000-b399dc5e8324895bef282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 40V, Negative-QTOFsplash10-0006-6930000000-95579f686cf729c65a222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 10V, Negative-QTOFsplash10-0gi0-0829000000-8c84a51e9e11593d1cd52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 20V, Negative-QTOFsplash10-0gi4-3849000000-6305fce231bb3e0b71bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 40V, Negative-QTOFsplash10-0ugl-3940000000-d7838720f0f845c19ee72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 10V, Positive-QTOFsplash10-00di-0009000000-c8e6150e81e908b0971e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 20V, Positive-QTOFsplash10-0l6r-0946000000-c51245f8d3561a8a0bd02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ochratoxin B 40V, Positive-QTOFsplash10-0fml-1920000000-ad9d01b16eda880f5d9b2021-09-24Wishart 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 IDFDB000490
KNApSAcK IDC00037570
Chemspider ID529965
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound609663
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .