ContaminantDB: Aflatoxin B2

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2010-04-15 16:55:14 UTC

Update Date

2026-03-26 20:31:52 UTC

Accession Number

CHEM002638

Identification

Common Name

Aflatoxin B2

Class

Small Molecule

Description

Aflatoxin B2 is a metabolite of Aspergillus flavus.

Contaminant Sources

FooDB Chemicals
IARC Carcinogens Group 1
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Ester
Ether
Food Toxin
Fungal Toxin
Furocoumarin
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Aflatoxin b2, (6ar-cis)-isomer	MeSH
Aflatoxin b2 alpha	HMDB
Dihydroafflatoxin b1	HMDB
Dihydroaflatoxin b1	HMDB
Dihydroaflatoxine b1	HMDB
Aflatoxin b2	MeSH

Chemical Formula

C₁₇H₁₄O₆

Average Molecular Mass

314.290 g/mol

Monoisotopic Mass

314.079 g/mol

CAS Registry Number

7220-81-7

IUPAC Name

11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),10,13(17)-tetraene-16,18-dione

Traditional Name

aflatoxin B2

SMILES

COC1=CC2=C(C3CCOC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2

InChI Identifier

InChI=1S/C17H14O6/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/h6,8,17H,2-5H2,1H3

InChI Key

WWSYXEZEXMQWHT-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Difurocoumarocyclopentenones

Alternative Parents

Substituents

Difurocoumarocyclopentenone
Difurocoumarin
Benzopyran
1-benzopyran
Coumaran
Anisole
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tetrahydrofuran
Lactone
Ketone
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a secondary metabolite (CPD-10177 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless to pale yellow crystals.

Experimental Properties

Property	Value
Melting Point	310°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.39 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.57	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.49 m³·mol⁻¹	ChemAxon
Polarizability	30.9 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0039000000-610151efc4e68c6939eb	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-0039000000-610151efc4e68c6939eb	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0080-0190000000-cdd965c2769a1d578fba	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4l-0390000000-85aa7a411b52bfa748ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0009000000-306b14c6051334a7615d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-6117c5ee93218e1f3ee4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0069000000-e8cfaba3e9fca310b5f8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0abi-0090000000-c1f0b82710fe7cf4a4fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4l-0390000000-47a96f38cc39db4215d8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0abi-0090000000-f0166b802bbb8d10da36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0039000000-d446a0adf08fa67d4d10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0094000000-7a6e82836edee1f981c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02t9-1490000000-29ed28bb149ea2411c26	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0039000000-baac6939881949076644	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1097000000-d8269f211e11ae5c68b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-2190000000-9ea1e85b37f388c7c5e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-7c7169b7540bc9455826	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0049000000-5b4008ed9ce6ec916cef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-0492000000-e1dbbfaed1432ac0341f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-2ba875095a8aafa31ef7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0019000000-519c5d1d27095e3ff42b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0091000000-6cb76c17d0d87928e540	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-4189000000-6bab374050b1044ec494	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (5)

Mechanism of Toxicity

Aflatoxins produce singlet oxygen upon their exposure to UV (365-nm) light. Singlet oxygen in turn activates them to mutagens and DNA binding species. Aflatoxin metabolites can intercalate into DNA and alkylate the bases through their epoxide moiety, binding particularity to N7-guanine bases. In addition to randomly mutating DNA, this is thought to cause mutations in the p53 gene, an important gene in preventing cell cycle progression when there are DNA mutations, or signaling apoptosis. (11, 3, 4) The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. (10)

Metabolism

Aflatoxin B2 is metabolized in the liver by microsomal monooxygenases to the less toxic reactive metabolite alfatoxin M2. Aflatoxin B2 is also proposed to be metabolized to B1, which in turn is transformed to M1. (2, 13)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans (9)

Uses/Sources

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. Crops which are frequently affected 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). The toxin can also be found in the milk of animals which are fed contaminated feed. Thus, aflatoxins are usually encountered in thecontext of chronic exposure, via food intake or secondary to the handling of foodstuffs. (13)

Minimum Risk Level

Not Available

Health Effects

The main target organ in mammals is the liver so aflatoxicosis is primarily a hepatic disease. Protracted exposure to aflatoxins may cause liver damage and necrosis, cholestasis, and hepatomas. Moreover, protracted exposure to aflatoxins has been associated with hepatocellular carcinoma, acute hepatitis, Reye's syndrome, bile duct cell proliferation, periportal fibrosis, hemorrhages, mucous membrane jaundice, fatty liver changes, cirrhosis in malnourished children, and kwashiorkor. However, aflatoxins accumulate in the presence of liver disease, and the association with hepatic cancer is confounded by the occurrence of hepatitis-B. Thus, it is not clear in these various instances whether aflatoxin is a primary cause of the disease, is an innocent bystander which accumulates secondary to the disease process, or is a contributing cause in conjunction with other factors. It is also mutagenic and teratogenic. Inhaled aflatoxins may produce pulmonary adenomatosis. Aflatoxins modify the immune system by affecting antibody formation, complement, cell-mediated immunity, and phagocytosis. (1, 13) Furocoumarins can cause photosensitization dermatitis especially if these compounds come into contact with the skin. Some furocoumarins, especially bifunctional furocoumarins, are known to be carcinogenic (6). Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs. Limited evidence of carcinogenic effect. (10)

Symptoms

A broad range of symptoms can be found depending upon dosage, including, vomiting, abdominal pain, hemorrhage, and pulmonary edema. (12)

Treatment

Administration of phonobarbital enhances hepatic transformation activities and also protects against AFB-induced toxicity, carcinogenicity and DNA binding in vivo. In cases of ingestion, feeding large quantities of an adsorbent such as activated charcoal may be used. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. (1, 12)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0035208

FooDB ID

FDB013855

Phenol Explorer ID

Not Available

KNApSAcK ID