AFLATOXIN G1

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H12O7
Molecular Weight	328.273
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C([C@@H]3C=CO[C@@H]3O2)C4=C1C5=C(C(=O)OCC5)C(=O)O4

InChI

InChIKey=XWIYFDMXXLINPU-WNWIJWBNSA-N

InChI=1S/C17H12O7/c1-20-9-6-10-12(8-3-5-22-17(8)23-10)14-11(9)7-2-4-21-15(18)13(7)16(19)24-14/h3,5-6,8,17H,2,4H2,1H3/t8-,17+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H12O7
Molecular Weight	328.273
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25445582
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/4101421 | https://www.ncbi.nlm.nih.gov/pubmed/24090735 | https://www.ncbi.nlm.nih.gov/pubmed/220299 | https://www.ncbi.nlm.nih.gov/pubmed/28671585

Aflatoxin G1 ((7aR,10aS)-3,4,7a,10a-tetrahydro-5-methoxy-1H,12H-furo[3',2':4,5]furo[2,3-h]pyrano[3,4-c][1]benzopyran-1,12-dione) is a food contaminant produced by various species of the common soil fungus, Aspergillus and is associated with toxicity and hepatocarcinogenicity in human and animal populations. Epidemiological studies have shown that Aflatoxin G1 is one of the most frequently detected contaminating mycotoxins in grains and foodstuffs in areas with high-incidence of lung and esophageal cancer

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Caspase-3 21 Target ID: CHEMBL2334 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24090735	Activator 1447
JNK cascade 4 Target ID: GO:0007254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24090735	Activator 1447
p38MAPK cascade 9 Target ID: GO:0038066 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24090735	Activator 1447
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28671585	Crosslinking Agent 83

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Oral administration of aflatoxin G₁ induces chronic alveolar inflammation associated with lung tumorigenesis.	2015-02-03	25445582
Cytochrome P450 2A13 is an efficient enzyme in metabolic activation of aflatoxin G1 in human bronchial epithelial cells.	2013-09	23907605
Aflatoxins B(1), B(2) and G(1) modulate cytokine secretion and cell surface marker expression in J774A.1 murine macrophages.	2012-08	22445859
Aflatoxins upregulate CYP3A4 mRNA expression in a process that involves the PXR transcription factor.	2011-08-28	21641981
Aflatoxin G1 reduces the molecular expression of HLA-I, TAP-1 and LMP-2 of adult esophageal epithelial cells in vitro.	2010-06-02	20381597
Evaluation of the detoxifying effect of yeast glucomannan on aflatoxicosis in broilers as assessed by gross examination and histopathology.	2005-06	16050196
Protective effect of L-carnitine against oxidative damage caused by experimental chronic aflatoxicosis in quail (Coturnix coturnix).	2005	16156127
Increased cytotoxicity of food-borne mycotoxins toward human cell lines in vitro via enhanced cytochrome p450 expression using the MTT bioassay.	1999-11	11189750
Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae.	1990-12-25	2271712
Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response in Salmonella typhimurium TA 1535/pSK1002.	1989-06-15	2655891

Patents

Sample Use Guides

In Vivo Use Guide

Female Balb/c mice were treated with AFG1 (100mkg/kg) three times weekly for 6 months.

Route of Administration: Oral

In Vitro Use Guide

A549 cells (ATCC) were routinely cultured in DMEM, supplemented with 100 U/ ml penicillin, 100 U/ml streptomycin, and 10% fetal bovine serum (FBS), in 5% CO2/ 95% air. AFG1 was diluted in DMSO (10 lg AFG1/lL DMSO) and added to the cultures to obtain a final concentration of 0.5, 2, 4 and 10 mg /L respectively. 0.1% DMSO was added to A549 cells as a solvent control. The cells were then treated with DMSO or various concentrations of AFG1 for 24 h.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:09:57 GMT 2025` Edited by `admin` on `Mon Mar 31 21:09:57 GMT 2025`
Record UNII	1DB78J7PUD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(7AR,CIS)3,4,7A,10A-TETRAHYDRO-5-METHOXY-1H,12H- FURO(3',2':4,5)FURO(2,3-H)PYRANO(3,4-C)CHROMENE-1,12-DIONE

Preferred Name

English

AFLATOXIN G1

Common Name

English

AFLATOXIN G1 [HSDB]

Common Name

English

AFLATOXIN G1 [MI]

Common Name

English

1H,12H-FURO(3',2':4,5)FURO(2,3-H)PYRANO(3,4-C)(1)BENZOPYRAN-1,12-DIONE, 3,4,7A,10A-TETRAHYDRO-5-METHOXY-, (7AR-CIS)-

Systematic Name

English

1H,12H-FURO(3',2':4,5)FURO(2,3-H)PYRANO(3,4-C)(1)BENZOPYRAN- 1,12-DIONE, 3,4,7A,10A-TETRAHYDRO-5-METHOXY-

Common Name

English

1H,12H-FURO(3',2':4,5)FURO(2,3-H)PYRANO(3,4-C)(1)BENZOPYRAN- 1,12-DIONE,3,4,7A,10A-TETRAHYDRO-5-METHOXY-, (7AR-CIS)-

Common Name

English

Code System Code Type Description

MERCK INDEX

m1442