You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-05-17 01:24:47 UTC
Update Date2018-05-20 09:58:08 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. N-Acetylmuramate is soluble (in water) and a weakly acidic compound (based on its pKa). N-Acetylmuramate has been primarily detected in feces. N-Acetylmuramate can be biosynthesized from 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucopyranose.
Structure
Thumb
Synonyms
ValueSource
N-Acetyl-D-muramoateChEBI
N-Acetylmuramic acidChEBI
N-Acetyl-D-muramoic acidGenerator
N-Acetylisomuramic acidMeSH
Acetylmuramic acidMeSH
2-acetamido-4-O-(1-Carboxyethyl)-2-deoxyglucoseMeSH
2-acetamido-3-O-((S)-1-Carboxyethyl)-2-deoxy-D-glucoseMeSH
2-acetamido-4-O-(1-Carboxyethyl)-2-deoxyglucose, (beta-D)-isomerMeSH
4-O-NAcMurMeSH
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
DescriptionThis compound 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:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility53.6 g/LALOGPS
logP-1.8ALOGPS
logP-1.7ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)3.56ChemAxon
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w3c-9770000000-6ea5f3aa50ac02ceef70View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-000i-2521239000-848f1d85486e26e1ccb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-2090000000-c59d76c37f09e9eca3a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9300000000-c6df138f6c4ab6417c59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-55e3ebaf861e8b735486View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-5b2b2975a5058255fb08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-88058a65b8efd6f05e46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004l-0190000000-66ecbfcb7919cabff2d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0910000000-5c3a9f9f979ccddac74dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-d14f3f8f84118002dfa5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000j-7900000000-471fe5d4e276658b1949View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000t-9200000000-6adb1379e733b7e32568View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fbc-0090000000-77705b9680f576293a4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zor-2190000000-a2225fd0cee643a4a97cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi3-9570000000-18bd313b1db1b7d803eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udv-4190000000-937234965abe7cb8d291View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zmr-7390000000-092457bbe47b41978e3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9400000000-f12dba9036850e101fedView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>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
FoodDB 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
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