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Showing Compound 8,9-Epoxyaflatoxin B1 (FDB014707)

Record Information
Version1.0
Creation date2010-04-08 22:11:25 UTC
Update date2015-07-20 23:10:29 UTC
Primary IDFDB014707
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8,9-Epoxyaflatoxin B1
DescriptionProb. ultimate carcinogen of Aflatoxin B1 2,3-Epoxyaflatoxin B1 is formed due to the metabolism of aflatoxin B1 (AFB1) by ; CYP2A13, an enzyme predominantly expressed in human respiratory tract, but 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, most notably Aspergillus flavus and Aspergillus parasiticus. 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 favorable for its growth. Favorable 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).
CAS Number42583-46-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-Aflatoxin B1 15a,16a-epoxidemanual
(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
[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
2,3-Epoxyaflatoxin B1biospider
8,9-Epoxy-aflatoxin b1HMDB
8,9-Epoxyaflatoxin B1manual
Aflatoxin B1 2,3-epoxidebiospider
Aflatoxin B1 8,9-epoxidebiospider
Aflatoxin B1 8,9-oxidebiospider
Aflatoxin B1 epoxidebiospider
Aflatoxin B1 exo-8,9-epoxidebiospider
Aflatoxin B1 exo-8,9-oxidebiospider
Aflatoxin B1-2,3-oxidebiospider
Aflatoxin B1-8,9-epoxidebiospider
Aflatoxin b1, 2,3-oxideHMDB
exo-Aflatoxin B1-8,9-epoxidebiospider
Predicted Properties
PropertyValueSource
Water Solubility1.56 g/LALOGPS
logP1.33ALOGPS
logP1.56ChemAxon
logS-2.3ALOGPS
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
Polarizability31.07 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H12O7
IUPAC name12-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
InChI IdentifierInChI=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
InChI KeyKHBXRZGALJGBPA-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C3C4OC4OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2
Average Molecular Weight328.273
Monoisotopic Molecular Weight328.058302738
Classification
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 DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 62.20%; H 3.68%; O 34.12%DFC
Melting PointMp 300° (phase transition at 230°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS8,9-Epoxyaflatoxin B1, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00rl-1091000000-46a63489cf68b5f2b170Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-b8ea0b324a7e8c2c7a612016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02di-0097000000-f0fa28b0d6cfec1836092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00o1-1290000000-e67ce15c691e462328622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0029000000-2ed27746a3a2caebf5fe2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0059000000-bbff7fd1becc9f8b22d22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4090000000-749a6bd3aaf05f94c88a2016-08-03View Spectrum
NMRNot Available
ChemSpider ID94566
ChEMBL IDNot Available
KEGG Compound IDC19586
Pubchem Compound ID104756
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06558
CRC / DFC (Dictionary of Food Compounds) IDJHZ87-P:JVD05-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2300011
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glutathione S-transferase Mu 3GSTM3P21266
Glutathione S-transferase omega-1GSTO1P78417
Glutathione S-transferase A2GSTA2P09210
Glutathione S-transferase PGSTP1P09211
Glutathione S-transferase Mu 2GSTM2P28161
Glutathione S-transferase Mu 1GSTM1P09488
Microsomal glutathione S-transferase 3MGST3O14880
Glutathione S-transferase A1GSTA1P08263
Microsomal glutathione S-transferase 1MGST1P10620
Glutathione S-transferase Mu 4GSTM4Q03013
Glutathione S-transferase Mu 5GSTM5P46439
Microsomal glutathione S-transferase 2MGST2Q99735
Glutathione S-transferase A5GSTA5Q7RTV2
Glutathione S-transferase A3GSTA3Q16772
Glutathione S-transferase A4GSTA4O15217
Glutathione S-transferase omega-2GSTO2Q9H4Y5
Epoxide hydrolase 1EPHX1P07099
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference