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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H14O6
Molecular Weight 314.2895
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AFLATOXIN B2

SMILES

COC1=CC2=C([C@@H]3CCO[C@@H]3O2)C4=C1C5=C(C(=O)CC5)C(=O)O4

InChI

InChIKey=WWSYXEZEXMQWHT-WNWIJWBNSA-N
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/t8-,17+/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21038701 | https://goo.gl/bx6rLb | https://www.ncbi.nlm.nih.gov/pubmed/27863407 | https://www.ncbi.nlm.nih.gov/pubmed/19699076

Aflatoxin B2 is the dihydro derivative of aflatoxin B1, a naturally occurring mycotoxin and food contaminant that is a likely pathogen that causes hepatocellular carcinoma. Aflatoxin B2 induces mitochondria-mediated apoptosis via the production of reactive oxygen species (ROS) and promotion of the translocation of Bax and cytochrome c between mitochondria and the cytosol, triggering the formation of apoptosomes. Aflatoxin B2 also inhibited the phosphoinositide 3-kinase/Akt/ mammalian target of rapamycin (PI3K/Akt/mTOR) pathway by activating PI3K, Akt, and mTOR and inhibiting their phosphorylation, contributing to the pro-autophagic activity of Aflatoxin B2.

Originator

Sources: Nature (London, United Kingdom) (1963), 200, (4911), 1101.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Aflatoxins--health risk factors].
2010-11-03
Patents

Sample Use Guides

The broilers were given 0 mg/kg/d (control), 0.2 mg/kg/d, 0.4 mg/kg/d, and 0.8 mg/kg/d AFB2 for 21 d.
Route of Administration: Oral
The HepG2 cell line (American Type Culture Collection (ATCC) HB-8065) was cultured in Eagle’s minimal essential medium (EMEM) containing 10% (v/v) fetal bovine serum (FBS). Cells were seeded in a 24-well plate at a cell plating density of 105 cells per well. After reaching 80% confluency, the cells were serum-starved overnight in EMEM containing 1% FBS. Following serum starvation, the cells were treated with UV-treated aflatoxin (Aflatoxin B2, 0.46mkg/ml) samples for 24 h. Following sample treatment, the cell viability was assayed using XTT assay (ATCC, Manassas, VA) as per the manufacturer’s protocol.
Name Type Language
2,3,6AALPHA,8,9,9AALPHA-HEXAHYDRO-4- METHOXYCYCLOPENTA(C)FURO(3',2':4,5)FURO(2,3-H)(1)BENZOPYRAN- 1,11-DIONE
Preferred Name English
AFLATOXIN B2
HSDB  
Common Name English
CYCLOPENTA(C)FURO(3',2':4,5)FURO(2,3-H)(1)BENZOPYRAN-1,11-DIONE, 2,3,6A,8,9,9A-HEXAHYDRO-4-METHOXY-, (6AR-CIS)-
Systematic Name English
CYCLOPENTA(C)FURO(3',2':4,5)FURO(2,3-H)(1)BENZOPYRAN-1,11-DIONE, 2,3,6A,8,9,9A-HEXAHYDRO-4-METHOXY-, (6AR,9AS)-
Systematic Name English
DIHYDROAFLATOXIN B1
Common Name English
AFLATOXIN B [MI]
Common Name English
DIHYDROAFLATOXINE B1
Common Name English
AFLATOXIN B2 [HSDB]
Common Name English
Code System Code Type Description
CAS
7220-81-7
Created by admin on Mon Mar 31 21:09:57 GMT 2025 , Edited by admin on Mon Mar 31 21:09:57 GMT 2025
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SMS_ID
300000053067
Created by admin on Mon Mar 31 21:09:57 GMT 2025 , Edited by admin on Mon Mar 31 21:09:57 GMT 2025
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FDA UNII
7SKR7S646P
Created by admin on Mon Mar 31 21:09:57 GMT 2025 , Edited by admin on Mon Mar 31 21:09:57 GMT 2025
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PUBCHEM
2724360
Created by admin on Mon Mar 31 21:09:57 GMT 2025 , Edited by admin on Mon Mar 31 21:09:57 GMT 2025
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HSDB
3454
Created by admin on Mon Mar 31 21:09:57 GMT 2025 , Edited by admin on Mon Mar 31 21:09:57 GMT 2025
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ECHA (EC/EINECS)
230-618-8
Created by admin on Mon Mar 31 21:09:57 GMT 2025 , Edited by admin on Mon Mar 31 21:09:57 GMT 2025
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CHEBI
48209
Created by admin on Mon Mar 31 21:09:57 GMT 2025 , Edited by admin on Mon Mar 31 21:09:57 GMT 2025
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MESH
C029753
Created by admin on Mon Mar 31 21:09:57 GMT 2025 , Edited by admin on Mon Mar 31 21:09:57 GMT 2025
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EPA CompTox
DTXSID70222535
Created by admin on Mon Mar 31 21:09:57 GMT 2025 , Edited by admin on Mon Mar 31 21:09:57 GMT 2025
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