Chemicals and Drugs

Acetylmuramyl-Alanyl-Isoglutamine

Peptidoglycan immunoadjuvant originally isolated from bacterial cell wall fragments; also acts as pyrogen and may cause arthritis; stimulates both humoral and cellular immunity.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

Peptidoglycan immunoadjuvant originally isolated from bacterial cell wall fragments; also acts as pyrogen and may cause arthritis; stimulates both humoral and cellular immunity.

Chemical Identity

Chemical Information

Molecular Formula
C19H32N4O11
Molecular Weight
492.5 g/mol
IUPAC Name
(2R)-2-[[(2S)-2-[[(2R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
InChIKey
SNTUQIQTAZQYIG-PUFOHHGRSA-N
SMILES
C[C@@H](C(=O)N[C@H](CCC(=O)N)C(=O)O)NC(=O)[C@@H](C)O[C@@H]1[C@H]([C@H](O[C@@H]([C@H]1O)CO)O)NC(=O)C
MeSH Unique ID
D000119
Source
PubChem CID 16214783

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

11 entry terms
  • Acetylmuramyl Alanyl Isoglutamine
  • Muramyl Dipeptide
  • Alanyl Isoglutamine, Acetylmuramyl
  • Dipeptide, Muramyl
  • Isoglutamine, Acetylmuramyl Alanyl
  • Mur-NAc-L-Ala-D-isoGln
  • N-Acetyl-Muramyl-L-Alanyl-D-Glutamic-alpha-Amide
  • N-Acetylmuramyl-L-Alanyl-D-Isoglutamine
  • Mur NAc L Ala D isoGln
  • N Acetyl Muramyl L Alanyl D Glutamic alpha Amide
  • N Acetylmuramyl L Alanyl D Isoglutamine

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, drug effects, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

83(79); was see under GLYCOPEPTIDES 1979-82

MeSH Record

Previous Indexing

  • Glycopeptides (1971-1978)
  • Peptides (1966-1970)
  • Polysaccharides (1966-1970)

MeSH Hierarchy

Tree Numbers

  1. D09w.067w.550.050
  2. D09w.811w.522.050
  3. D12.644w.233w.050

MeSH Record

NLM Classification

QW 800

AMA Style

References

  1. National Library of Medicine. Acetylmuramyl-Alanyl-Isoglutamine. Medical Subject Headings (MeSH). 2026. Unique ID D000119. http://id.nlm.nih.gov/mesh/2026/D000119
  2. Acetylmuramyl-Alanyl-Isoglutamine. In: Wikidata. https://www.wikidata.org/wiki/Q27463570
  3. Acetylmuramyl-Alanyl-Isoglutamine. In: PubChem Compound. CID 16214783. https://pubchem.ncbi.nlm.nih.gov/compound/16214783