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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-05-17 01:24:47 UTC
Update Date2021-09-14 15:18:57 UTC
HMDB IDHMDB0060493
Secondary Accession Numbers
  • HMDB60493
Metabolite Identification
Common NameN-Acetylmuramate
DescriptionN-Acetylmuramate, also known as acetylmuramic acid or 4-O-nacmur, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. These are carbohydrate derivatives containing a hexose moeity in which the oxygen atom is replaced by an n-acyl group. N-Acetylmuramate is a moderately basic compound (based on its pKa). N-Acetylmuramate exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1563866067
Synonyms
ValueSource
N-Acetyl-D-muramoateChEBI
N-Acetylmuramic acidChEBI
N-Acetyl-D-muramoic acidGenerator
N-Acetylisomuramic acidHMDB
Acetylmuramic acidHMDB
2-Acetamido-4-O-(1-carboxyethyl)-2-deoxyglucoseHMDB
2-Acetamido-3-O-((S)-1-carboxyethyl)-2-deoxy-D-glucoseHMDB
2-Acetamido-4-O-(1-carboxyethyl)-2-deoxyglucose, (beta-D)-isomerHMDB
4-O-NAcMurHMDB
N-AcetylmuramateGenerator
N-Acetyl-D-muramateGenerator
Chemical FormulaC11H19NO8
Average Molecular Weight293.2705
Monoisotopic Molecular Weight293.111066589
IUPAC Name(2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
Traditional Name(2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=O
InChI Identifier
InChI=1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1
InChI KeyMNLRQHMNZILYPY-MKFCKLDKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • Muramic_acid
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Sugar acid
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility53.6 g/LALOGPS
logP10(-1.8) g/LALOGPS
logP10(-1.7) g/LChemAxon
logS10(-0.74) g/LALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)1.39ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.04 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.88 m³·mol⁻¹ChemAxon
Polarizability27.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.04731661259
DarkChem[M-H]-162.46431661259
DeepCCS[M+H]+170.72730932474
DeepCCS[M-H]-168.83130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetylmuramate[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=O3876.3Standard polar33892256
N-Acetylmuramate[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=O2366.7Standard non polar33892256
N-Acetylmuramate[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=O2293.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylmuramate,1TMS,isomer #1CC(O)=N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O2195.9Semi standard non polar33892256
N-Acetylmuramate,1TMS,isomer #2CC(O)=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O2202.2Semi standard non polar33892256
N-Acetylmuramate,1TMS,isomer #3CC(O)=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O2202.6Semi standard non polar33892256
N-Acetylmuramate,1TMS,isomer #4CC(=N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C2260.8Semi standard non polar33892256
N-Acetylmuramate,1TMS,isomer #5CC(O)=N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C2155.5Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #1CC(=N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C2214.2Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #10CC(=N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2204.5Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #2CC(O)=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O2202.3Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #3CC(O)=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O2223.2Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #4CC(O)=N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C2146.7Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #5CC(=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C2224.2Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #6CC(O)=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O2229.2Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #7CC(O)=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C2175.1Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #8CC(=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C2262.5Semi standard non polar33892256
N-Acetylmuramate,2TMS,isomer #9CC(O)=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C2182.0Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #1CC(=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C2217.0Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #10CC(=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2200.6Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #2CC(=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C2232.5Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #3CC(=N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2186.6Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #4CC(O)=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O2224.8Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #5CC(O)=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C2205.7Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #6CC(O)=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C2209.6Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #7CC(=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C2229.0Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #8CC(=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2187.0Semi standard non polar33892256
N-Acetylmuramate,3TMS,isomer #9CC(O)=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C2227.5Semi standard non polar33892256
N-Acetylmuramate,4TMS,isomer #1CC(=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C2231.2Semi standard non polar33892256
N-Acetylmuramate,4TMS,isomer #2CC(=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2205.9Semi standard non polar33892256
N-Acetylmuramate,4TMS,isomer #3CC(=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2205.1Semi standard non polar33892256
N-Acetylmuramate,4TMS,isomer #4CC(O)=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C2242.3Semi standard non polar33892256
N-Acetylmuramate,4TMS,isomer #5CC(=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2215.2Semi standard non polar33892256
N-Acetylmuramate,5TMS,isomer #1CC(=N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C2251.7Semi standard non polar33892256
N-Acetylmuramate,1TBDMS,isomer #1CC(O)=N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O2408.8Semi standard non polar33892256
N-Acetylmuramate,1TBDMS,isomer #2CC(O)=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O2424.7Semi standard non polar33892256
N-Acetylmuramate,1TBDMS,isomer #3CC(O)=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O2427.8Semi standard non polar33892256
N-Acetylmuramate,1TBDMS,isomer #4CC(=N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C2505.7Semi standard non polar33892256
N-Acetylmuramate,1TBDMS,isomer #5CC(O)=N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C2418.2Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #1CC(=N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C2659.0Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #10CC(=N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2673.5Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #2CC(O)=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O2632.6Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #3CC(O)=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O2637.0Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #4CC(O)=N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C2610.5Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #5CC(=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C2683.1Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #6CC(O)=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O2643.8Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #7CC(O)=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C2633.7Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #8CC(=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C2677.4Semi standard non polar33892256
N-Acetylmuramate,2TBDMS,isomer #9CC(O)=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C2631.3Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #1CC(=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C2877.6Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #10CC(=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2879.6Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #2CC(=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C2906.2Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #3CC(=N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2870.5Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #4CC(O)=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O2870.6Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #5CC(O)=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C2842.5Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #6CC(O)=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C2860.7Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #7CC(=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C2883.8Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #8CC(=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2892.5Semi standard non polar33892256
N-Acetylmuramate,3TBDMS,isomer #9CC(O)=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C2845.6Semi standard non polar33892256
N-Acetylmuramate,4TBDMS,isomer #1CC(=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O)O[Si](C)(C)C(C)(C)C3075.4Semi standard non polar33892256
N-Acetylmuramate,4TBDMS,isomer #2CC(=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3039.5Semi standard non polar33892256
N-Acetylmuramate,4TBDMS,isomer #3CC(=N[C@H]1C(O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3081.0Semi standard non polar33892256
N-Acetylmuramate,4TBDMS,isomer #4CC(O)=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C3039.9Semi standard non polar33892256
N-Acetylmuramate,4TBDMS,isomer #5CC(=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3065.5Semi standard non polar33892256
N-Acetylmuramate,5TBDMS,isomer #1CC(=N[C@H]1C(O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[C@H](C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3221.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylmuramate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w3c-9770000000-6ea5f3aa50ac02ceef702017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylmuramate GC-MS (5 TMS) - 70eV, Positivesplash10-000i-2521239000-848f1d85486e26e1ccb12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylmuramate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , negative-QTOFsplash10-0006-2090000000-c59d76c37f09e9eca3a82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , negative-QTOFsplash10-000i-9300000000-c6df138f6c4ab6417c592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-55e3ebaf861e8b7354862017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-5b2b2975a5058255fb082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-88058a65b8efd6f05e462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , positive-QTOFsplash10-004l-0190000000-66ecbfcb7919cabff2d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , positive-QTOFsplash10-000i-0910000000-5c3a9f9f979ccddac74d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , positive-QTOFsplash10-000i-1900000000-d14f3f8f84118002dfa52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , positive-QTOFsplash10-000j-7900000000-471fe5d4e276658b19492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate LC-ESI-QQ , positive-QTOFsplash10-000t-9200000000-6adb1379e733b7e325682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate 20V, Negative-QTOFsplash10-000i-9000000000-1810df27f3e35e27f6072021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate 10V, Negative-QTOFsplash10-000i-9200000000-e95563bae7228e910e002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate 20V, Positive-QTOFsplash10-000i-2900000000-430a64e2453d7fb5e2302021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate 40V, Positive-QTOFsplash10-000t-9200000000-de6c564d9edc459bf8a92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate 10V, Positive-QTOFsplash10-002r-0920000000-22b37e7c518af19310d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate 40V, Positive-QTOFsplash10-000t-9200000000-c0d7500b262a7d7e84042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate 20V, Positive-QTOFsplash10-000i-1900000000-71199c968272be0cb2022021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate 10V, Positive-QTOFsplash10-002r-0910000000-a1354bedf1ac9db6c3c62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmuramate 40V, Negative-QTOFsplash10-052u-9000000000-b9701ee162fa5c198fa72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmuramate 10V, Positive-QTOFsplash10-0fbc-0090000000-77705b9680f576293a4f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmuramate 20V, Positive-QTOFsplash10-0zor-2190000000-a2225fd0cee643a4a97c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmuramate 40V, Positive-QTOFsplash10-0fi3-9570000000-18bd313b1db1b7d803ee2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmuramate 10V, Negative-QTOFsplash10-0udv-4190000000-937234965abe7cb8d2912015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmuramate 20V, Negative-QTOFsplash10-0zmr-7390000000-092457bbe47b41978e3c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmuramate 40V, Negative-QTOFsplash10-0pb9-9400000000-f12dba9036850e101fed2015-09-15Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4575341
KEGG Compound IDC02713
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Acetylmuramic_acid
METLIN IDNot Available
PubChem Compound5462244
PDB IDNot Available
ChEBI ID21615
Food Biomarker OntologyNot Available
VMH IDACMAM
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Pattern receptor that binds to murein peptidoglycans (PGN) of Gram-positive bacteria. Has bactericidal activity towards Gram-positive bacteria. May kill Gram-positive bacteria by interfering with peptidoglycan biosynthesis. Binds also to Gram-negative bacteria, and has bacteriostatic activity towards Gram-negative bacteria. Plays a role in innate immunity.
Gene Name:
PGLYRP1
Uniprot ID:
O75594
Molecular weight:
Not Available
Reactions
N-Acetylmuramoyl-Ala + Water → N-Acetylmuramate + L-Alaninedetails
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Pattern receptor that binds to murein peptidoglycans (PGN) of Gram-positive bacteria. Has bactericidal activity towards Gram-positive bacteria. May kill Gram-positive bacteria by interfering with peptidoglycan biosynthesis. Binds also to Gram-negative bacteria, and has bacteriostatic activity towards Gram-negative bacteria. Plays a role in innate immunity.
Gene Name:
PGLYRP3
Uniprot ID:
Q96LB9
Molecular weight:
Not Available
Reactions
N-Acetylmuramoyl-Ala + Water → N-Acetylmuramate + L-Alaninedetails
General function:
Not Available
Specific function:
Pattern receptor that binds to murein peptidoglycans (PGN) of Gram-positive bacteria. Has bactericidal activity towards Gram-positive bacteria. May kill Gram-positive bacteria by interfering with peptidoglycan biosynthesis. Binds also to Gram-negative bacteria, and has bacteriostatic activity towards Gram-negative bacteria. Plays a role in innate immunity.
Gene Name:
PGLYRP4
Uniprot ID:
Q96LB8
Molecular weight:
Not Available
Reactions
N-Acetylmuramoyl-Ala + Water → N-Acetylmuramate + L-Alaninedetails
General function:
Not Available
Specific function:
May play a scavenger role by digesting biologically active peptidoglycan (PGN) into biologically inactive fragments. Has no direct bacteriolytic activity.
Gene Name:
PGLYRP2
Uniprot ID:
Q96PD5
Molecular weight:
Not Available
Reactions
N-Acetylmuramoyl-Ala + Water → N-Acetylmuramate + L-Alaninedetails