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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H19NO8
Molecular Weight 293.2705
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N-ACETYLMURAMIC ACID

SMILES

C[C@@H](O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](NC(C)=O)C=O)C(O)=O

InChI

InChIKey=SOARVSUSWULNDI-TVVSKHENSA-N
InChI=1S/C11H19NO8/c1-5(11(18)19)20-10(9(17)8(16)4-14)7(3-13)12-6(2)15/h3,5,7-10,14,16-17H,4H2,1-2H3,(H,12,15)(H,18,19)/t5-,7+,8-,9-,10-/m1/s1

HIDE SMILES / InChI
Molecular Formula C11H19NO8
Molecular Weight 293.2705
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

N-acetylmuramic acid (MurNAc) is a bacterial cell wall component. Peptidoglycan, also called murein, is a polymer that consists of long glycan chains that are cross-linked via flexible peptide bridges to form a strong but elastic structure that protects the underlying protoplast from lysing due to the high internal osmotic pressure. The peptidoglycan is the only cell wall polymer common to both gram-negative and gram-positive bacteria. The glycan chain is built up of alternating, β-1,4-linked N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) subunits. The chemistry of the glycan chains varies only slightly between different bacteria.

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Peptidoglycan types of bacterial cell walls and their taxonomic implications.
1972 Dec
Antagonistic effect of peptidoglycan of Streptococcus sanguinis on lipopolysaccharide of major periodontal pathogens.
2015 Aug

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: THP-1 cells were co-treated with the LPS in the presence of N-acetylmuramic acid and N-acetylglucosamine, as components of PGN, and the competition binding assay to CD14 and LBP was performed. N-acetylmuramic acid inhibited the induction of inflammatory cytokine expression by LPS and the binding of LPS to CD14 or LBP whereas N-acetylglucosamine did not show such effect. Collectively, the results suggest that S. sanguinis PGN inhibited the cytokine expression induced by the LPS of periodontopathogens due to the inhibition of LPS binding to LBP and CD14. N-acetylmuramic acid of PGN may play a role in inhibition of the LPS binding of periodontopathogens to CD14 and LBP.
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:45:59 UTC 2023
Edited
by admin
on Fri Dec 15 17:45:59 UTC 2023
Record UNII
246FXU111L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N-ACETYLMURAMIC ACID
Common Name English
D-GLUCOSE, 2-(ACETYLAMINO)-3-O-(1-CARBOXYETHYL)-2-DEOXY-, (R)-
Systematic Name English
MURAMIC ACID, N-ACETYL-
Common Name English
N-ACETYLMURAMIC ACID [MI]
Common Name English
(+)-N-ACETYLMURAMIC ACID
Common Name English
D-GLUCOSE, 2-ACETAMIDO-3-O-(D-1-CARBOXYETHYL)-2-DEOXY-
Common Name English
Code System Code Type Description
CAS
99880-82-7
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
SUPERSEDED
ECHA (EC/EINECS)
234-214-2
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID70893663
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
CAS
38-44-8
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
SUPERSEDED
CHEBI
47571
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
CAS
637028-12-7
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
SUPERSEDED
CAS
10597-89-4
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
CHEBI
47966
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
PUBCHEM
82756
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
FDA UNII
246FXU111L
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
WIKIPEDIA
N-ACETYLMURAMIC ACID
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
CAS
1856-93-5
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
SUPERSEDED
MESH
C031651
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
CHEBI
21615
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
MERCK INDEX
m7659
Created by admin on Fri Dec 15 17:45:59 UTC 2023 , Edited by admin on Fri Dec 15 17:45:59 UTC 2023
PRIMARY
NIH
NCATS
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