Showing metabocard for 2,3-Epoxyaflatoxin B1 (BMDB0006558)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:23:20 UTC
Update Date2020-04-22 15:17:51 UTC
BMDB IDBMDB0006558
Secondary Accession Numbers
  • BMDB06558
Metabolite Identification
Common Name2,3-Epoxyaflatoxin B1
Description2,3-Epoxyaflatoxin B1, also known as aflatoxin B1 8,9-epoxide or afb epoxide, 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. 2,3-Epoxyaflatoxin B1 is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,3-Epoxyaflatoxin B1 exists in all living organisms, ranging from bacteria to humans.
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 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2091000000-3e7fccd8ab55a4b8afe0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-fbf1af1a8568f56e50efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0096000000-33744bd389e8fca44efeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fba-2390000000-ec31f9517f188988d668View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0029000000-0cb8f21eba1630039dc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0049000000-b7a57848a1bc684e5b2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9060000000-53f728c814df49ee82b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-a6e8d4715f87e5602d4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-d83f4a2899f653ea3031View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-0098000000-656b4b27c8e2657b0072View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-3eb691afb29ed57b3f5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-9595278280fed091bf1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-1197000000-ef7f7a710cfcfd7ccdd4View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006558
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available