Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H12O6 |
| Molecular Weight | 312.2736 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C([C@@H]3C=CO[C@@H]3O2)C4=C1C5=C(C(=O)CC5)C(=O)O4
InChI
InChIKey=OQIQSTLJSLGHID-WNWIJWBNSA-N
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
| Molecular Formula | C17H12O6 |
| Molecular Weight | 312.2736 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Aflatoxin B1 is a very potent carcinogen produced by Aspergillus flavus and related fungi that grow on improperly stored food such as corn, rice, and peanuts. Dietary exposure to aflatoxin B1 is associated with an increased incidence of hepatocellular carcinoma, especially given co-infection with hepatitis B virus. Mechanism of carcinogenicity involves metabolic activation to aflatoxin B1-8,9 exo-epoxide by cytochrome p450 and formation of adducts with guanine DNA base.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Aflatoxin B1 augments the synthesis of corticotropin releasing hormone in JEG-3 placental cells. | 2015-07-25 |
|
| Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study. | 2015-05 |
|
| Toxicity of aflatoxin B1 towards the vitamin D receptor (VDR). | 2015-02 |
|
| Sulforaphane, a cancer chemopreventive agent, induces pathways associated with membrane biosynthesis in response to tissue damage by aflatoxin B1. | 2015-01-01 |
|
| Effects of aflatoxin B₁, fumonisin B₁ and their mixture on the aryl hydrocarbon receptor and cytochrome P450 1A induction. | 2015-01 |
|
| Hepatotoxic effects of mycotoxin combinations in mice. | 2014-12 |
|
| Effect of selenium supplementation on aflatoxin B₁-induced histopathological lesions and apoptosis in bursa of Fabricius in broilers. | 2014-12 |
|
| Lophirones B and C extenuate AFB1-mediated oxidative onslaught on cellular proteins, lipids, and DNA through Nrf-2 expression. | 2014-12 |
|
| In vivo treatment with aflatoxin B1 increases DNA oxidation, base excision repair activity and 8-oxoguanine DNA glycosylase 1 levels in mouse lung. | 2014-07-03 |
|
| Genetic or pharmacologic activation of Nrf2 signaling fails to protect against aflatoxin genotoxicity in hypersensitive GSTA3 knockout mice. | 2014-06 |
|
| Genome-wide miRNA-profiling of aflatoxin B1-induced hepatic injury using deep sequencing. | 2014-04-21 |
|
| Up-regulation of nucleotide excision repair in mouse lung and liver following chronic exposure to aflatoxin B₁ and its dependence on p53 genotype. | 2014-03-01 |
|
| Aflatoxin B1 disrupts the androgen biosynthetic pathway in rat Leydig cells. | 2014-03 |
|
| The role of NAD(+)-dependent isocitrate dehydrogenase 3 subunit α in AFB1 induced liver lesion. | 2014-01-30 |
|
| Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action. | 2014 |
|
| HepG2 cells simultaneously expressing five P450 enzymes for the screening of hepatotoxicity: identification of bioactivable drugs and the potential mechanism of toxicity involved. | 2013-06 |
|
| Integrated analysis of transcriptomics and metabonomics profiles in aflatoxin B1-induced hepatotoxicity in rat. | 2013-05 |
|
| The effects of aflatoxin B1 on transporters and steroid metabolizing enzymes in JEG-3 cells. | 2013-04-26 |
|
| Identification of novel liver-specific mRNAs in plasma for biomarkers of drug-induced liver injury and quantitative evaluation in rats treated with various hepatotoxic compounds. | 2013-03 |
|
| Detection of genotoxic and non-genotoxic carcinogens in Xpc(-/-)p53(+/-) mice. | 2013-01-15 |
|
| RNA-Seq profiling reveals novel hepatic gene expression pattern in aflatoxin B1 treated rats. | 2013 |
|
| Alpha-class glutathione S-transferases in wild turkeys (Meleagris gallopavo): characterization and role in resistance to the carcinogenic mycotoxin aflatoxin B1. | 2013 |
|
| Comparison of genotoxicant-modified transcriptomic responses in conventional and epigenetically stabilized primary rat hepatocytes with in vivo rat liver data. | 2012-11 |
|
| Cytochrome P450 2A13 mediates aflatoxin B1-induced cytotoxicity and apoptosis in human bronchial epithelial cells. | 2012-10-28 |
|
| Comparison of hepatocarcinogen-induced gene expression profiles in conventional primary rat hepatocytes with in vivo rat liver. | 2012-09 |
|
| A single neonatal exposure to aflatoxin b1 induces prolonged genetic damage in two loci of mouse liver. | 2012-08 |
|
| Aflatoxins B(1), B(2) and G(1) modulate cytokine secretion and cell surface marker expression in J774A.1 murine macrophages. | 2012-08 |
|
| Testing an aflatoxin B1 gene signature in rat archival tissues. | 2012-05-21 |
|
| Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs. | 2012-05 |
|
| Characterization of primary human hepatocytes, HepG2 cells, and HepaRG cells at the mRNA level and CYP activity in response to inducers and their predictivity for the detection of human hepatotoxins. | 2012-04 |
|
| Identification of early target genes of aflatoxin B1 in human hepatocytes, inter-individual variability and comparison with other genotoxic compounds. | 2012-01-15 |
|
| The ToxTracker assay: novel GFP reporter systems that provide mechanistic insight into the genotoxic properties of chemicals. | 2012-01 |
|
| Promotion of hepatocarcinogenesis by perfluoroalkyl acids in rainbow trout. | 2012-01 |
|
| Human embryonic stem cell derived hepatocyte-like cells as a tool for in vitro hazard assessment of chemical carcinogenicity. | 2011-12 |
|
| 2'-Deoxyguanosine as a surrogate trapping agent for DNA reactive drug metabolites. | 2011-11-10 |
|
| Functional characterization of alpha-class glutathione s-transferases from the Turkey (meleagris gallopavo). | 2011-11 |
|
| Development and evaluation of a genomic signature for the prediction and mechanistic assessment of nongenotoxic hepatocarcinogens in the rat. | 2011-11 |
|
| Seasonal variation in TP53 R249S-mutated serum DNA with aflatoxin exposure and hepatitis B virus infection. | 2011-11 |
|
| Effect of aflatoxin B1 on nuclear receptors PXR, CAR, and AhR and their target cytochromes P450 mRNA expression in primary cultures of human hepatocytes. | 2011-10-14 |
|
| Validation of a genotoxicity test based on p53R2 gene expression in human lymphoblastoid cells. | 2011-09-18 |
|
| Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. | 2011-09 |
|
| Aflatoxins upregulate CYP3A4 mRNA expression in a process that involves the PXR transcription factor. | 2011-08-28 |
|
| Metabolism of aflatoxin B1 in turkey liver microsomes: the relative roles of cytochromes P450 1A5 and 3A37. | 2011-08-01 |
|
| Genomic profiling uncovers a molecular pattern for toxicological characterization of mutagens and promutagens in vitro. | 2011-07 |
|
| Aflatoxin B1-DNA adduct formation and mutagenicity in livers of neonatal male and female B6C3F1 mice. | 2011-07 |
|
| Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents. | 2011-03-24 |
|
| New short term prediction method for chemical carcinogenicity by hepatic transcript profiling following 28-day toxicity tests in rats. | 2011 |
|
| Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae. | 1990-12-25 |
|
| Effects of non-genotoxic hepatocarcinogens phenobarbital and nafenopin on phenotype and growth of different populations of altered foci in rat liver. | 1989 |
|
| Lack of expression of glutathione-S-transferase P, gamma-glutamyl transpeptidase, and alpha-fetoprotein messenger RNAs in liver tumors induced by peroxisome proliferators. | 1988-09-01 |
Patents
Sample Use Guides
Aflatoxin B1 is ingested with contaminated food. Studies showed that aflatoxin B1 can also penetrate skin.
Route of Administration:
Other
Bronchial and colonic specimens were incubated with [3H]Aflatoxin B1 (AFB1) (0.5 uM). For identification of the AFB,-DNA adduct, the mucosae were pooled from 20 and 60 explants from the bronchus and the colon, respectively, homogenized in Tris-sodium dodecyl sulfate buffer, incubated with proteinase K for 2 hr, and extracted with water-saturated phenol. After centrifugation at 10,000 x g for 30 mm, DNA was isolated from the upper phase by precipitation with ice-cold ethanol and kept overnight at -20°C. DNA was redissolved in 0.1 M Tris-HCI buffer (pH 6.5), treated with RNase I at 37° for 1 hr, and extracted twice with chloroform/phenol (1/1). The DNA solution was kept -20° until identification of the adduct.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:07:45 GMT 2025
by
admin
on
Mon Mar 31 20:07:45 GMT 2025
|
| Record UNII |
9N2N2Y55MH
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C213
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
1162-65-8
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
214-603-3
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
300000053081
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
186907
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
2504
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
Aflatoxin B1
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
529592
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
D016604
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
C1315
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
DTXSID9020035
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
2282017
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
m1441
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | Merck Index | ||
|
9N2N2Y55MH
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
9N2N2Y55MH
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY | |||
|
3453
Created by
admin on Mon Mar 31 20:07:45 GMT 2025 , Edited by admin on Mon Mar 31 20:07:45 GMT 2025
|
PRIMARY |