8,9-Epoxyaflatoxin B1 (CHEM029780)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:24:43 UTC
Update Date2026-04-06 09:25:38 UTC
Accession NumberCHEM029780
Identification
Common Name8,9-Epoxyaflatoxin B1
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass328.273 g/mol
Monoisotopic Mass328.058 g/mol
CAS Registry Number42583-46-0
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
SMILESCOC1=CC2=C(C3C4OC4OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability30.93 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2091000000-3e7fccd8ab55a4b8afe0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-fbf1af1a8568f56e50efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0096000000-33744bd389e8fca44efeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fba-2390000000-ec31f9517f188988d668Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0029000000-0cb8f21eba1630039dc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0049000000-b7a57848a1bc684e5b2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9060000000-53f728c814df49ee82b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-a6e8d4715f87e5602d4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-d83f4a2899f653ea3031Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-0098000000-656b4b27c8e2657b0072Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-3eb691afb29ed57b3f5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-9595278280fed091bf1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-1197000000-ef7f7a710cfcfd7ccdd4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006558
FooDB IDFDB014707
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2300011
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID94566
ChEBI ID30725
PubChem Compound ID104756
Kegg Compound IDC19586
YMDB IDNot Available
ECMDB IDM2MDB004130
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
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.