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Record Information
Version1.0
Created at2006-05-22 15:12:45 UTC
Updated at2021-06-29 00:47:43 UTC
NP-MRD IDNP0000016
Secondary Accession NumbersNone
Natural Product Identification
Common NameMuramic acid
DescriptionMuramic acid is an amino sugar acid. 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. Muramic 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. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls. In terms of chemical composition, it is the ether of lactic acid and glucosamine.
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 Mass251.2338 Da
Monoisotopic Mass251.10050 Da
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 TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Eubacteria
  • Species Where Detected
    Species NameSourceReference
    Escherichia coliKNApSAcK Database
    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 ParentsNot Available
    SubstituentsNot Available
    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
    External Links
    HMDB IDHMDB0003254
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB023131
    KNApSAcK IDC00019555
    Chemspider ID17216223
    KEGG Compound IDC06470
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkMuramic acid
    METLIN ID3381
    PubChem Compound22833605
    PDB IDNot Available
    ChEBI ID28118
    Good Scents IDNot Available
    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 ]