Muramyl Dipeptide
(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
Molecular Identity
Muramyl Dipeptide
(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
PubChem CID: 451714
Muramyl dipeptide is a glycopeptide that is N-propionyl-L-alanyl-D-alpha-glutamine in which the pro-R hydrogen of the propionyl group has been replaced by the oxygen at position 3 of 2-acetamido-2-deoxy-beta-D-glucopyranose. A peptidoglycan constituent of both Gram-positive and Gram-negative bacteria. It has a role as an immunological adjuvant. It is a conjugate acid of a N-acetyl-beta-D-muramoyl-L-alanyl-D-isoglutamine(1-).
2D Structure
Properties
C19H32N4O11
Molecular Formula
492.50
Molecular Weight
g/mol
492.2068
Exact Mass
Da
-3.7
XLogP
Drug-like (Lipinski: < 5)
247
TPSA
May have limited oral absorption
8
H-Bond Donors
11
H-Bond Acceptors
765
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Muramyl DipeptideCHEBI:59414N2-(N-(N-Acetylmuramoyl)-L-alanyl)-D-alpha-glutamine(4R)-4-[[(2S)-2-[[(2R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acidN-acetylmuramyl dipeptide(4R)-4-(((2S)-2-(((2R)-2-((2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl)oxypropanoyl)amino)propanoyl)amino)-5-amino-5-oxopentanoic acidGlyTouCan:G33008YIRefChem:1048409G33008YI258-696-92U7S2HVO9687420-48-2MurNAc-L-Ala-gamma-D-GluN-Acetylmuramyl-L-alanyl-D-isoglutamineAcetylmuramyl-L-alanyl-D-isoglutamine
Data from PubChem (NCBI)
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