Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:20:16 UTC
Update Date2022-03-07 03:17:44 UTC
HMDB IDHMDB0060430
Secondary Accession Numbers
  • HMDB60430
Metabolite Identification
Common NameAflatoxin B1 diol
DescriptionAflatoxin B1 diol belongs to the class of organic compounds known as difurocoumarocyclopentenones. These are polycyclic aromatic compounds containing a cyclopenten-2-one ring fused to the coumarin moiety of the difurocoumarin skeleton. Aflatoxin B1 diol is an extremely weak basic (essentially neutral) compound (based on its pKa). Aflatoxin B1 diol exists in all living organisms, ranging from bacteria to humans. These are polycyclic aromatic compounds containing a cyclopenten-2-one ring fused to the coumarin moiety of the difurocoumarin skeleton.
Structure
Data?1563866059
Synonyms
ValueSource
Aflatoxin b1-2,3-dihydrodiolKegg
2,3-Dihydro-2,3-dihydroxyaflatoxin b(1), 14C-labeledHMDB
Aflatoxin b1-2,3-diolHMDB
2,3-Dihydroxy-2,3-dihydroaflatoxin b1HMDB
2,3-Dihydro-2,3-dihydroxyaflatoxin b(1)HMDB
Chemical FormulaC17H14O8
Average Molecular Weight346.2883
Monoisotopic Molecular Weight346.068867424
IUPAC Name(3R,4R,5R,7S)-4,5-dihydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),10,13(17)-tetraene-16,18-dione
Traditional Name(3R,4R,5R,7S)-4,5-dihydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),10,13(17)-tetraene-16,18-dione
CAS Registry NumberNot Available
SMILES
COC1=CC2=C([C@@H]3[C@@H](O)[C@H](O)O[C@@H]3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2
InChI Identifier
InChI=1S/C17H14O8/c1-22-7-4-8-11(12-13(19)16(21)25-17(12)23-8)14-10(7)5-2-3-6(18)9(5)15(20)24-14/h4,12-13,16-17,19,21H,2-3H2,1H3/t12-,13-,16-,17+/m1/s1
InChI KeyJRZBEIPOZPNWID-KFZJALRRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as difurocoumarocyclopentenones. These are polycyclic aromatic compounds containing a cyclopenten-2-one ring fused to the coumarin moiety of the difurocoumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentDifurocoumarocyclopentenones
Alternative Parents
Substituents
  • Difurocoumarocyclopentenone
  • Difurocoumarin
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Lactone
  • Ketone
  • Hemiacetal
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.33 g/LALOGPS
logP0.52ALOGPS
logP0.39ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)11.34ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area111.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity80.52 m³·mol⁻¹ChemAxon
Polarizability32.71 ųChemAxon
Number of Rings5ChemAxon
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]+176.89531661259
DarkChem[M-H]-176.01331661259
DeepCCS[M+H]+186.26930932474
DeepCCS[M-H]-183.87430932474
DeepCCS[M-2H]-216.95630932474
DeepCCS[M+Na]+192.18230932474
AllCCS[M+H]+177.732859911
AllCCS[M+H-H2O]+174.632859911
AllCCS[M+NH4]+180.632859911
AllCCS[M+Na]+181.532859911
AllCCS[M-H]-180.832859911
AllCCS[M+Na-2H]-180.132859911
AllCCS[M+HCOO]-179.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Aflatoxin B1 diolCOC1=CC2=C([C@@H]3[C@@H](O)[C@H](O)O[C@@H]3O2)C2=C1C1=C(C(=O)CC1)C(=O)O24453.2Standard polar33892256
Aflatoxin B1 diolCOC1=CC2=C([C@@H]3[C@@H](O)[C@H](O)O[C@@H]3O2)C2=C1C1=C(C(=O)CC1)C(=O)O23104.4Standard non polar33892256
Aflatoxin B1 diolCOC1=CC2=C([C@@H]3[C@@H](O)[C@H](O)O[C@@H]3O2)C2=C1C1=C(C(=O)CC1)C(=O)O23309.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aflatoxin B1 diol,1TMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@H]1[C@@H](O2)O[C@@H](O)[C@@H]1O[Si](C)(C)C3089.9Semi standard non polar33892256
Aflatoxin B1 diol,1TMS,isomer #2COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@H]1[C@@H](O2)O[C@@H](O[Si](C)(C)C)[C@@H]1O3102.2Semi standard non polar33892256
Aflatoxin B1 diol,2TMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@H]1[C@@H](O2)O[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3144.9Semi standard non polar33892256
Aflatoxin B1 diol,1TBDMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@H]1[C@@H](O2)O[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C3293.6Semi standard non polar33892256
Aflatoxin B1 diol,1TBDMS,isomer #2COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@H]1[C@@H](O2)O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O3300.8Semi standard non polar33892256
Aflatoxin B1 diol,2TBDMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@H]1[C@@H](O2)O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C3546.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aflatoxin B1 diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-016r-1059000000-78fca54d390a1264a7952017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aflatoxin B1 diol GC-MS (2 TMS) - 70eV, Positivesplash10-00bi-9064700000-87615cd5b84e6f27b25e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aflatoxin B1 diol 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 - Aflatoxin B1 diol 10V, Positive-QTOFsplash10-0002-0009000000-b60b83a6466e830124f42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 20V, Positive-QTOFsplash10-004j-0069000000-4e344585b8e2f7082b272017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 40V, Positive-QTOFsplash10-0nor-4492000000-b9ffdbb1d390c14330812017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 10V, Negative-QTOFsplash10-0002-0019000000-75c6e6dfa7c793c200d12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 20V, Negative-QTOFsplash10-002b-0059000000-b1a05eb98f8ca8707f5a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 40V, Negative-QTOFsplash10-0006-2090000000-129dfdaec819b708246f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 10V, Positive-QTOFsplash10-0002-0009000000-b5ba7323fe2beec24e512021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 20V, Positive-QTOFsplash10-0002-0019000000-8f112959c502917bc83e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 40V, Positive-QTOFsplash10-0gbj-0079000000-a63b003ded85c979c7142021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 10V, Negative-QTOFsplash10-0002-0009000000-c11eb9aa945116b2d7392021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 20V, Negative-QTOFsplash10-0002-1019000000-75516536561914d69d9a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin B1 diol 40V, Negative-QTOFsplash10-00ko-1093000000-4b2f5dfa62882d261cfd2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC19588
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3035008
PDB IDNot Available
ChEBI ID82580
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Biotransformation enzyme that catalyzes the hydrolysis of arene and aliphatic epoxides to less reactive and more water soluble dihydrodiols by the trans addition of water.
Gene Name:
EPHX1
Uniprot ID:
P07099
Molecular weight:
52948.48
Reactions
2,3-Epoxyaflatoxin B1 + Water → Aflatoxin B1 dioldetails