Record Information
Version1.0
Creation date2010-04-08 22:11:29 UTC
Update date2019-11-26 03:10:48 UTC
Primary IDFDB014816
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAflatoxin B1
DescriptionProduction by Aspergillus flavus and Aspergillus parasiticus. Toxin causing Turkey X disease. One of the most potent carcinogens known in animals. Potential food contaminant especies in grains and nuts 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). Aflatoxin B1 is found in cereals and cereal products, nuts, and corn.
CAS Number1162-65-8
Structure
Thumb
Synonyms
SynonymSource
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
(-)-Aflatoxin B1db_source
Aflatoxin B1manual
Aflatoxin B1 Dihydrochloride, (6aR-cis)-Isomerbiospider
Aflatoxin B1, cis(+,-)-Isomerbiospider
Aflatoxin-B1biospider
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
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
Chemical FormulaC17H12O6
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
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C2C3=C(C(=O)CC3)C(=O)OC2=C2C3C=COC3OC2=C1
Average Molecular Weight312.2736
Monoisotopic Molecular Weight312.063388116
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
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 65.39%; H 3.87%; O 30.74%DFC
Melting PointMp 268-269° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -562 (c, 0.115 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0098000000-ddc3fa0269c995f2f419JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0098000000-ddc3fa0269c995f2f419JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1090000000-8165fc6f4a64219431f5JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0aor-0039000000-2a3e295d237d548522c8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0039000000-e651352b2d5971a2b5fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0095000000-0bc98f6f0902591a79f9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-11p1-1190000000-c2826a9129632e518aaaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0039000000-d18bfc13c789e0966a83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0098000000-0962df76a8d67f37f6cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-2090000000-ba82fd9309bad5df957bJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-03fr-7894000000-57075e5f64c138201081JSpectraViewer | MoNA
ChemSpider ID13758
ChEMBL IDNot Available
KEGG Compound IDC06800
Pubchem Compound ID14403
Pubchem Substance IDNot Available
ChEBI ID2504
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06552
CRC / DFC (Dictionary of Food Compounds) IDJHZ87-P:JWJ74-I
EAFUS IDNot Available
Dr. Duke IDAFLATOXIN B-1
BIGG ID2300004
KNApSAcK IDC00000546
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
Aflatoxin B1 aldehyde reductase member 4AKR7LQ8NHP1
Aflatoxin B1 aldehyde reductase member 2AKR7A2O43488
Aflatoxin B1 aldehyde reductase member 3AKR7A3O95154
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).