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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-23 15:36:14 UTC
Update Date2020-10-09 21:04:24 UTC
HMDB IDHMDB0006552
Secondary Accession Numbers
  • HMDB06552
Metabolite Identification
Common NameAflatoxin B1
DescriptionAflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus. 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 favourable for its growth. Favourable 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).
Structure
Data?1582752391
Synonyms
ValueSource
2,3,6Aalpha,9aalpha-tetrahydro-4-methoxycyclopenta(c)furo(3',2':4,5)furo(2,3-H)(1)benzopyran-1,11-dioneChEBI
Aflatoxin b1 dihydrochloride, (6ar-cis)-isomerHMDB
Aflatoxin b1, (6ar-cis)-isomer, 14C-labeledHMDB
Aflatoxin b1, (6ar-cis)-isomer, 2H-labeledHMDB
Aflatoxin b1, cis(+,-)-isomerHMDB
Aflatoxin bHMDB
HSDB 3453HMDB
Aflatoxin b1, (6ar-cis)-isomer, 3H-labeledHMDB
HSDB-3453HMDB
(-)-Aflatoxin b1HMDB
AFB1HMDB
Aflatoxin B1HMDB
Chemical FormulaC17H12O6
Average Molecular Weight312.2736
Monoisotopic Molecular Weight312.063388116
IUPAC Name(3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^{2,9}.0^{3,7}.0^{13,17}]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione
Traditional Name(3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^{2,9}.0^{3,7}.0^{13,17}]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione
CAS Registry Number1162-65-8
SMILES
[H][C@]12OC=C[C@@]1([H])C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O
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/t8-,17+/m0/s1
InChI KeyOQIQSTLJSLGHID-WNWIJWBNSA-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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Polarizability30.14 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0098000000-ddc3fa0269c995f2f419Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0098000000-ddc3fa0269c995f2f419Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0aor-0039000000-2a3e295d237d548522c8Spectrum
MSMass Spectrum (Electron Ionization)splash10-03fr-7894000000-57075e5f64c138201081Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0009 +/- 0.00097 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.009 (0.008-0.014) uMAdult (>18 years old)BothReye's Syndrome details
Associated Disorders and Diseases
Disease References
Reye's syndrome
  1. Tsuboi S, Nakagawa T, Tomita M, Seo T, Ono H, Kawamura K, Iwamura N: Detection of aflatoxin B1 in serum samples of male Japanese subjects by radioimmunoassay and high-performance liquid chromatography. Cancer Res. 1984 Mar;44(3):1231-4. [PubMed:6420055 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014816
KNApSAcK IDC00000546
Chemspider ID162470
KEGG Compound IDC06800
BioCyc IDCPD-4592
BiGG IDNot Available
Wikipedia LinkAflatoxin
METLIN IDNot Available
PubChem Compound186907
PDB IDNot Available
ChEBI ID2504
Food Biomarker OntologyNot Available
VMH IDAFLATOXIN
MarkerDB IDMDB00000487
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)Download (PDF)
General References
  1. 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. [PubMed:17214555 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
General function:
Energy production and conversion
Specific function:
Catalyzes the NADPH-dependent reduction of succinic semialdehyde to gamma-hydroxybutyrate. May have an important role in producing the neuromodulator gamma-hydroxybutyrate (GHB). Has broad substrate specificity. Has NADPH-dependent aldehyde reductase activity towards 2-carboxybenzaldehyde, 2-nitrobenzaldehyde and pyridine-2-aldehyde (in vitro). Can reduce 1,2-naphthoquinone and 9,10-phenanthrenequinone (in vitro). Can reduce the dialdehyde protein-binding form of aflatoxin B1 (AFB1) to the non-binding AFB1 dialcohol. May be involved in protection of liver against the toxic and carcinogenic effects of AFB1, a potent hepatocarcinogen.
Gene Name:
AKR7A2
Uniprot ID:
O43488
Molecular weight:
39588.65
General function:
Involved in oxidoreductase activity
Specific function:
Can reduce the dialdehyde protein-binding form of aflatoxin B1 (AFB1) to the non-binding AFB1 dialcohol. May be involved in protection of liver against the toxic and carcinogenic effects of AFB1, a potent hepatocarcinogen
Gene Name:
AKR7A3
Uniprot ID:
O95154
Molecular weight:
37206.1
General function:
Involved in oxidoreductase activity
Specific function:
Can reduce the dialdehyde protein-binding form of aflatoxin B1 (AFB1) to the non-binding AFB1 dialcohol. May be involved in protection of liver against the toxic and carcinogenic effects of AFB1, a potent hepatocarcinogen
Gene Name:
AKR7L
Uniprot ID:
Q8NHP1
Molecular weight:
36963.5