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Record Information
Version1.0
Created at2006-05-22 15:12:45 UTC
Updated at2020-09-11 01:33:48 UTC
NP-MRD IDNP0000016
Secondary Accession NumbersNone
Natural Product Identification
Common NameMuramic acid
DescriptionMuramic acid, also known as muramate or murexide, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Muramic acid is an amino sugar acid. Muramic acid is a very strong basic compound (based on its pKa). In terms of chemical composition, it is the ether of lactic acid and glucosamine. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls.
Structure
Thumb
Synonyms
ValueSource
MuramateGenerator
(+)-MuramateHMDB
(+)-Muramic acidHMDB
3-O-alpha-Carboxyethyl-D-glucosamineHMDB
3-O-alpha-Carboxyethyl-delta-glucosamineHMDB
Muramic acid hydrateHMDB
MurexideHMDB
(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoateHMDB
Chemical FormulaC9H17NO7
Average Molecular Weight251.2338
Monoisotopic Molecular Weight251.100501903
IUPAC Name(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
Traditional Name(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
CAS Registry Number1114-41-6
SMILES
C[C@@H](O[C@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C9H17NO7/c1-3(8(13)14)16-7-5(10)9(15)17-4(2-11)6(7)12/h3-7,9,11-12,15H,2,10H2,1H3,(H,13,14)/t3-,4-,5-,6-,7+,9-/m1/s1
InChI KeyMSFSPUZXLOGKHJ-LEISLEKSSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesEubacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Muramic_acid
  • Hexose monosaccharide
  • Amino saccharide
  • Sugar acid
  • Monosaccharide
  • Oxane
  • Amino acid or derivatives
  • Hemiacetal
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Alcohol
  • Primary alcohol
  • Primary amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point153 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility152 g/LALOGPS
logP-3.1ALOGPS
logP-4.6ChemAxon
logS-0.22ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)8.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area142.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.91 m³·mol⁻¹ChemAxon
Polarizability23.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0003254
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023131
KNApSAcK IDNot Available
Chemspider ID17216223
KEGG Compound IDC06470
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMuramic acid
METLIN ID3381
PubChem Compound22833605
PDB IDNot Available
ChEBI ID28118
References
General References
  1. Hoijer MA, Melief MJ, van Helden-Meeuwsen CG, Eulderink F, Hazenberg MP: Detection of muramic acid in a carbohydrate fraction of human spleen. Infect Immun. 1995 May;63(5):1652-7. [PubMed:7729869 ]
  2. Kozar MP, Krahmer MT, Fox A, Gray BM: Failure To detect muramic acid in normal rat tissues but detection in cerebrospinal fluids from patients with Pneumococcal meningitis. Infect Immun. 2000 Aug;68(8):4688-98. [PubMed:10899874 ]
  3. Fox A, Fox K, Christensson B, Harrelson D, Krahmer M: Absolute identification of muramic acid, at trace levels, in human septic synovial fluids in vivo and absence in aseptic fluids. Infect Immun. 1996 Sep;64(9):3911-5. [PubMed:8751949 ]
  4. Christensson B, Gilbart J, Fox A, Morgan SL: Mass spectrometric quantitation of muramic acid, a bacterial cell wall component, in septic synovial fluids. Arthritis Rheum. 1989 Oct;32(10):1268-72. [PubMed:2679561 ]
  5. Mollner S, Braun V: Murein hydrolase (N-acetyl-muramyl-L-alanine amidase) in human serum. Arch Microbiol. 1984 Dec;140(2-3):171-7. [PubMed:6152147 ]
  6. Chen T, Rimpilainen M, Luukkainen R, Mottonen T, Yli-Jama T, Jalava J, Vainio O, Toivanen P: Bacterial components in the synovial tissue of patients with advanced rheumatoid arthritis or osteoarthritis: analysis with gas chromatography-mass spectrometry and pan-bacterial polymerase chain reaction. Arthritis Rheum. 2003 Jun 15;49(3):328-34. [PubMed:12794787 ]
  7. Bal K, Larsson L: New and simple procedure for the determination of muramic acid in chemically complex environments by gas chromatography-ion trap tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 2000 Jan 28;738(1):57-65. [PubMed:10778926 ]