Record Information
Version2.0
Creation Date2012-07-30 14:55:06 -0600
Update Date2015-06-03 17:21:00 -0600
Secondary Accession Numbers
  • ECMDB21248
Identification
Name:N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid
Description:N-acetyl-d-glucosamine(anhydrous)n-acetylmuramic acid belongs to the class of Hexoses. These are monosaccharides in which the sugar unit is a hexose. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramate
Chemical Formula:C19H30N2O12
Weight:Average: 478.4477
Monoisotopic: 478.179874434
InChI Key:MWWQKONGFKUAEK-AJSMYUJSSA-N
InChI:InChI=1S/C19H30N2O12/c1-6(17(27)28)30-16-12(21-8(3)24)18-29-5-10(32-18)15(16)33-19-11(20-7(2)23)14(26)13(25)9(4-22)31-19/h6,9-16,18-19,22,25-26H,4-5H2,1-3H3,(H,20,23)(H,21,24)(H,27,28)/t6?,9-,10?,11-,12?,13-,14-,15?,16?,18?,19+/m1/s1
CAS number:Not Available
IUPAC Name:2-[(2-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy]propanoic acid
Traditional IUPAC Name:2-[(2-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy]propanoic acid
SMILES:CC(OC1C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2N=C(C)O)C2COC(O2)C1N=C(C)O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxepane
  • Oxane
  • Meta-dioxolane
  • Secondary alcohol
  • Acetal
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility13.4 g/LALOGPS
logP-1.3ALOGPS
logP-2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)1.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area209.32 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity103.4 m³·mol⁻¹ChemAxon
Polarizability45.47 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08i9-0010900000-bbda29640fb7ebab3ed5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ug0-1192400000-6c73ff68782ebdf56004View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-8988100000-835c46c0f926ef131820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05br-7255900000-f681ebb93205104715f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-5294700000-fd1526243bddae3345faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-9471000000-f13f57a4b77de3859153View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID45479497
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:
amiB
Uniprot ID:
P26365
Molecular weight:
47985
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides
Gene Name:
amiA
Uniprot ID:
P36548
Molecular weight:
31412
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:
amiC
Uniprot ID:
P63883
Molecular weight:
45634
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Cleaves GlcNAc linked beta-1,4 to MurNAc tripeptides
Gene Name:
nagZ
Uniprot ID:
P75949
Molecular weight:
37594
Reactions
Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides.
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Involved in both cell wall peptidoglycans recycling and beta-lactamase induction. Specifically cleaves the amide bond between the lactyl group of N-acetylmuramic acid and the alpha- amino group of the L-alanine in degradation products containing an anhydro N-acetylmuramyl moiety
Gene Name:
ampD
Uniprot ID:
P13016
Molecular weight:
20536
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.

Transporters

General function:
Involved in transmembrane transport
Specific function:
Probably acts as a permease in the beta-lactamase induction system and in peptidoglycan recycling
Gene Name:
ampG
Uniprot ID:
P0AE16
Molecular weight:
53245
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368