Chemicals and Drugs

Aflatoxin M1

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) (Pharmac Ther 50.443 1991). Primates & rat are sensitive while mouse and hamster are tolerant (Canc Res 29.236 1969).

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

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) (Pharmac Ther 50.443 1991). Primates & rat are sensitive while mouse and hamster are tolerant (Canc Res 29.236 1969).

Chemical Identity

Chemical Information

Molecular Formula
C17H12O7
Molecular Weight
328.27 g/mol
CAS Registry No.
6795-23-9
IUPAC Name
(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione
InChIKey
MJBWDEQAUQTVKK-IAGOWNOFSA-N
SMILES
COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C(=C1)O[C@@H]5[C@]4(C=CO5)O
MeSH Unique ID
D016607
Source
PubChem CID 15558498

MeSH Record

Classification

Broader headings

Related Concepts

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

5 entry terms
  • 4-Hydroxyaflatoxin B1
  • Aflatoxin M(1)
  • 4 Hydroxyaflatoxin B1
  • Aflatoxin M
  • Aflatoxin M1, cis(+-)-Isomer

MeSH Record

Aspects Covered

28 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, physiology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

Indexing Annotation

/antag permitted but consider also ANTITOXINS

MeSH Record

History Note

92; was AFLATOXIN (NM) 1980-91

MeSH Record

Previous Indexing

  • Aflatoxins (1969-1991)

MeSH Hierarchy

Tree Numbers

  1. D03w.383.663.283.119w.100w
  2. D03w.633.100.150.119w.100w
  3. D23.946w.587w.142w.100w

AMA Style

References

  1. National Library of Medicine. Aflatoxin M1. Medical Subject Headings (MeSH). 2026. Unique ID D016607. http://id.nlm.nih.gov/mesh/2026/D016607
  2. Aflatoxin M1. In: Wikipedia. https://en.wikipedia.org/wiki/Aflatoxin_M1
  3. Aflatoxin M1. In: Wikidata. https://www.wikidata.org/wiki/Q26998369
  4. Aflatoxin M1. In: PubChem Compound. CID 15558498. https://pubchem.ncbi.nlm.nih.gov/compound/15558498