Showing metabocard for Aflatoxin B1 (BMDB0006552)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:23:15 UTC
Update Date2020-04-22 15:17:49 UTC
BMDB IDBMDB0006552
Secondary Accession Numbers
  • BMDB06552
Metabolite Identification
Common NameAflatoxin B1
DescriptionAflatoxin B1 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. Thus, aflatoxin B1 is considered to be an aflatoxin lipid molecule. Aflatoxin B1 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Aflatoxin B1 is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AFB1HMDB
AFBIHMDB
HSDB-3453MeSH, HMDB
Aflatoxin bMeSH, HMDB
Aflatoxin b1, (6ar-cis)-isomer, 14C-labeledMeSH, HMDB
Aflatoxin b1, (6ar-cis)-isomer, 2H-labeledMeSH, HMDB
HSDB 3453MeSH, HMDB
Aflatoxin b1 dihydrochloride, (6ar-cis)-isomerMeSH, HMDB
Aflatoxin b1, cis(+,-)-isomerMeSH, HMDB
Aflatoxin b1, (6ar-cis)-isomer, 3H-labeledMeSH, HMDB
Chemical FormulaC17H12O6
Average Molecular Weight312.2736
Monoisotopic Molecular Weight312.063388116
IUPAC Name11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione
Traditional Nameaflatoxin
CAS Registry Number1162-65-8
SMILES
COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C2C3C=COC3OC2=C1
InChI Identifier
InChI=1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3
InChI KeyOQIQSTLJSLGHID-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
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Dihydrofuran
  • Lactone
  • Ketone
  • Ether
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
logP1.73ALOGPS
logP1.58ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)17.79ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area71.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.59 m³·mol⁻¹ChemAxon
Polarizability30.07 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0098000000-ddc3fa0269c995f2f419View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0098000000-ddc3fa0269c995f2f419View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1090000000-8165fc6f4a64219431f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0aor-0039000000-2a3e295d237d548522c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0039000000-e651352b2d5971a2b5fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0095000000-0bc98f6f0902591a79f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-11p1-1190000000-c2826a9129632e518aaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0039000000-d18bfc13c789e0966a83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0098000000-0962df76a8d67f37f6cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-2090000000-ba82fd9309bad5df957bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03fr-7894000000-57075e5f64c138201081View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014816
KNApSAcK IDC00000546
Chemspider IDNot Available
KEGG Compound IDC06800
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAflatoxin B1
METLIN IDNot Available
PubChem Compound14403
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceTrost, Barry M.; Toste, F. Dean. Palladium Catalyzed Kinetic and Dynamic Kinetic Asymmetric Transformations of g-Acyloxybutenolides. Enantioselective Total Synthesis of (+)-Aflatoxin B1 and B2a. Journal of the American Chemical Society (2003), 125(10), 30
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available