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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 15:50:53 UTC
Update Date2021-09-14 15:39:07 UTC
HMDB IDHMDB0006558
Secondary Accession Numbers
  • HMDB0142058
  • HMDB06558
Metabolite Identification
Common Name2,3-Epoxyaflatoxin B1
Description2,3-Epoxyaflatoxin B1 is formed due to the metabolism of aflatoxin B1 (AFB1) by CYP2A13, an enzyme predominantly expressed in the human respiratory tract. There is no detectable AFB1 epoxide formation by CYP2A6, which was also reported to be involved in the metabolic activation of AFB1 (PMID: 16385575 ). Aflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus. At least 13 different types of aflatoxin are produced in nature. Aflatoxin B1 is considered the most toxic and is produced by both Aspergillus flavus and Aspergillus parasiticus. The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favourable for its growth. Favourable conditions include high moisture content (at least 7%) and high temperature. Aflatoxins B1 (AFB1) are contaminants of improperly stored foods; they are potent genotoxic and carcinogenic compounds, exerting their effects through damage to DNA. They can also induce mutations that increase oxidative damage (PMID: 17214555 ). Crops which are frequently affected by Aspergillus contamination include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut). BioTransformer predicts that 2,3-epoxyaflatoxin B1 is a product of aflatoxin B1 metabolism via an epoxidation-of-vinyl-ether reaction catalyzed by CYP1A2 and CYP3A4 enzymes (PMID: 30612223 ).
Structure
Data?1582752391
Synonyms
ValueSource
Aflatoxin b1 2,3-epoxideChEBI
Aflatoxin b1 8,9-epoxideChEBI
Aflatoxin b1 exo-8,9-oxideChEBI
Aflatoxin b1-2,3-oxideChEBI
(6AS,7as,8ar,8BR)-2,3,6a,7a,8a,8b-hexahydro-4-methoxy-cyclopent[c]oxireno[4',5']furo[3',2':4,5]furo[2,3-H][1]benzopyran-1,10-dioneHMDB
8,9-Epoxy-aflatoxin b1HMDB
Aflatoxin b1 8,9-oxideHMDB
Aflatoxin b1 epoxideHMDB
Aflatoxin b1 exo-8,9-epoxideHMDB
Aflatoxin b1, 2,3-oxideHMDB
exo-Aflatoxin b1-8,9-epoxideHMDB
[6AS-(6aa,7ab,8ab,8ba)]-2,3,6a,7a,8a,8b-hexahydro-4-methoxy-cyclopent[c]oxireno[4',5']furo[3',2':4,5]furo[2,3-H][1]benzopyran-1,10-dioneHMDB
AFB epoxideHMDB
AFB1-2,3-oxideHMDB
Aflatoxin b1-8,9-epoxideHMDB
AFB1 8,9-oxideHMDB
2,3-Epoxyaflatoxin b1ChEBI
2,3-Epoxyaflatoxin B1HMDB
Chemical FormulaC17H12O7
Average Molecular Weight328.273
Monoisotopic Molecular Weight328.058302738
IUPAC Name(3R,4R,6S,8S)-12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione
Traditional Name(3R,4R,6S,8S)-12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione
CAS Registry Number42583-46-0
SMILES
[H][C@]12O[C@@H]3O[C@@H]3[C@@]1([H])C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O
InChI Identifier
InChI=1S/C17H12O7/c1-20-7-4-8-11(12-14-17(23-14)24-16(12)21-8)13-10(7)5-2-3-6(18)9(5)15(19)22-13/h4,12,14,16-17H,2-3H2,1H3/t12-,14-,16+,17+/m1/s1
InChI KeyKHBXRZGALJGBPA-IRWJRLHMSA-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 ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Meta-dioxane
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Lactone
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Oxirane
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.56 g/LALOGPS
logP10(1.33) g/LALOGPS
logP10(1.56) g/LChemAxon
logS10(-2.3) g/LALOGPS
pKa (Strongest Acidic)17.79ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area83.59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity77.01 m³·mol⁻¹ChemAxon
Polarizability30.93 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.91531661259
DarkChem[M-H]-172.52231661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Epoxyaflatoxin B1 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2091000000-3e7fccd8ab55a4b8afe02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Epoxyaflatoxin B1 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Epoxyaflatoxin B1 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 - 2,3-Epoxyaflatoxin B1 10V, Positive-QTOFsplash10-004i-0019000000-fbf1af1a8568f56e50ef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 20V, Positive-QTOFsplash10-004i-0096000000-33744bd389e8fca44efe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 40V, Positive-QTOFsplash10-0fba-2390000000-ec31f9517f188988d6682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 10V, Negative-QTOFsplash10-004i-0029000000-0cb8f21eba1630039dc12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 20V, Negative-QTOFsplash10-056r-0049000000-b7a57848a1bc684e5b2a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 40V, Negative-QTOFsplash10-002f-9060000000-53f728c814df49ee82b82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 10V, Positive-QTOFsplash10-004i-0009000000-a6e8d4715f87e5602d4e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 20V, Positive-QTOFsplash10-004i-0009000000-d83f4a2899f653ea30312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 40V, Positive-QTOFsplash10-01ti-0098000000-656b4b27c8e2657b00722021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 10V, Negative-QTOFsplash10-004i-0009000000-3eb691afb29ed57b3f5f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 20V, Negative-QTOFsplash10-004i-0009000000-9595278280fed091bf1c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Epoxyaflatoxin B1 40V, Negative-QTOFsplash10-056r-1197000000-ef7f7a710cfcfd7ccdd42021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB014707
KNApSAcK IDNot Available
Chemspider ID94566
KEGG Compound IDC19586
BioCyc IDNot Available
BiGG ID2300011
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound104756
PDB IDNot Available
ChEBI ID30725
Food Biomarker OntologyNot Available
VMH IDEAFLATOXIN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Amici M, Cecarini V, Pettinari A, Bonfili L, Angeletti M, Barocci S, Biagetti M, Fioretti E, Eleuteri AM: Binding of aflatoxins to the 20S proteasome: effects on enzyme functionality and implications for oxidative stress and apoptosis. Biol Chem. 2007 Jan;388(1):107-17. [PubMed:17214555 ]
  2. He XY, Tang L, Wang SL, Cai QS, Wang JS, Hong JY: Efficient activation of aflatoxin B1 by cytochrome P450 2A13, an enzyme predominantly expressed in human respiratory tract. Int J Cancer. 2006 Jun 1;118(11):2665-71. [PubMed:16385575 ]
  3. Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Enzymes

General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM2
Uniprot ID:
P28161
Molecular weight:
25744.395
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM1
Uniprot ID:
P09488
Molecular weight:
25711.555
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails
General function:
Involved in glutathione transferase activity
Specific function:
Also functions as a glutathione peroxidase.
Gene Name:
MGST3
Uniprot ID:
O14880
Molecular weight:
16516.185
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. May govern uptake and detoxification of both endogenous compounds and xenobiotics at the testis and brain blood barriers.
Gene Name:
GSTM3
Uniprot ID:
P21266
Molecular weight:
26559.32
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA1
Uniprot ID:
P08263
Molecular weight:
25630.785
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a wide substrate specificity.
Gene Name:
MGST1
Uniprot ID:
P10620
Molecular weight:
17598.45
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Active on 1-chloro-2,4-dinitrobenzene.
Gene Name:
GSTM4
Uniprot ID:
Q03013
Molecular weight:
25561.095
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM5
Uniprot ID:
P46439
Molecular weight:
25674.455
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails
General function:
Involved in enzyme activator activity
Specific function:
Can catalyze the production of LTC4 from LTA4 and reduced glutathione. Can catalyze the conjugation of 1-chloro-2,4-dinitrobenzene with reduced glutathione.
Gene Name:
MGST2
Uniprot ID:
Q99735
Molecular weight:
16620.4
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase and dehydroascorbate reductase activities. Has S-(phenacyl)glutathione reductase activity. Has also glutathione S-transferase activity. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA) and dimethylarsonic acid.
Gene Name:
GSTO1
Uniprot ID:
P78417
Molecular weight:
27565.6
Reactions
2,3-Epoxyaflatoxin B1 + Glutathione → Aflatoxin B1exo-8,9-epoxide-GSHdetails

Only showing the first 10 proteins. There are 19 proteins in total.