AFLATOXIN M1

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(C3=C1C4=C(C(=O)CC4)C(=O)O3)[C@]5(O)C=CO[C@@H]5O2

InChI

InChIKey=MJBWDEQAUQTVKK-IAGOWNOFSA-N

InChI=1S/C17H12O7/c1-21-9-6-10-13(17(20)4-5-22-16(17)23-10)14-12(9)7-2-3-8(18)11(7)15(19)24-14/h4-6,16,20H,2-3H2,1H3/t16-,17-/m1/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: http://www.hmdb.ca/metabolites/HMDB0030479 | https://www.ncbi.nlm.nih.gov/mesh/68016607 | http://www.wageningenacademic.com/doi/abs/10.3920/WMJ2014.1867

AFLATOXIN M1 is a 4-hydroxylated metabolite of AFLATOXIN B1, one of the MYCOTOXINS from ASPERGILLUS tainted food. It is associated with liver damage and cancer resulting from its P450 activation to the epoxide which alkylates DNA. Toxicity depends on the balance of liver enzymes that activate it (CYTOCHROME P-450) and others that detoxify it (GLUTATHIONE S TRANSFERASE). Primates and rat are sensitive while mouse and hamster are tolerant. Aflatoxin M1 (AFM1) is associated with carcinogenicity, genotoxicity, mutagenicity, and teratogenicity and as a result, represents a human health problem worldwide.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: http://www.inchem.org/documents/jecfa/jecmono/v47je02.htm \| http://www.jbc.org/content/262/16/7455.full.pdf \| http://www.t3db.ca/toxins/T3D3666	Interacts 323

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Aflatoxins upregulate CYP3A4 mRNA expression in a process that involves the PXR transcription factor.	2011-08-28	21641981
Metabolism of aflatoxin B1 in turkey liver microsomes: the relative roles of cytochromes P450 1A5 and 3A37.	2011-08-01	21616088
Cloning, expression and functional characterization of cytochrome P450 3A37 from turkey liver with high aflatoxin B1 epoxidation activity.	2010-08-16	20707407
Glycine N-methyltransferase affects the metabolism of aflatoxin B1 and blocks its carcinogenic effect.	2009-03-15	19146867

Patents

Sample Use Guides

In Vivo Use Guide

The intake of aflatoxin M1 from milk was calculated to be 6.8 ng/person per day for the European diet, 3.5 ng/person per day for the Latin American diet, 12 ng/person per day for the Far Eastern diet, 0.7 ng/person per day for the Middle Eastern diet, and 0.1 ng/person per day for the African diet. Intake calculated from the European regional diet was used for the assessment of cancer risk because this diet had the highest milk consumption. If all milk consumed were contaminated with aflatoxin M1 at the proposed maximum levels of 0.05 µg/kg or 0.5 µg/kg, the intake of aflatoxin M1 from milk in the European regional diet would be 15 ng/person per day or 150 ng/person per day, respectively.

Route of Administration: Oral

In Vitro Use Guide

The lowest toxic dose of Aflatoxin M1 (AFM1) was 0.6 ug per adult-rat hepatocytes culture. The lowest genotoxic dose of AFM1 was 0.05 ug/culture.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:56:03 GMT 2025` Edited by `admin` on `Mon Mar 31 21:56:03 GMT 2025`
Record UNII	I3020O28I3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AFLATOXIN M1

Common Name

English

AFLATOXIN M

Preferred Name

English

CYCLOPENTA(C)FURO(3',2':4,5)FURO(2,3-H)(1)BENZOPYRAN-1,11-DIONE, 2,3,6A,9A-TETRAHYDRO-9A-HYDROXY-4-METHOXY-, (6AR,9AR)-

Systematic Name

English

AFLATOXIN M1 [MI]

Common Name

English

AFM1

Common Name

English

Code System Code Type Description

MERCK INDEX

m1443