Record Information
Version2.0
Creation Date2012-05-31 14:48:38 -0600
Update Date2015-06-03 17:20:08 -0600
Secondary Accession Numbers
  • ECMDB20518
Identification
Name:N-Acetylmuramate 6-phosphate
DescriptionMurNAC-6-P is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. It is a substrate for N-acetylmuramate-6-phosphate etherase. This enzyme catalyzes the cleavage of the D-lactyl ether of MurNAC-6-P to produce GlcNAC-6-P and D lactate. It is required for growth on MurNAC and plays a role in cell wall biogenesis and peptidoglycan recylcing.
Structure
Thumb
Synonyms:
  • MurNAc-6-P
  • N-Acetylmuramate 6-phosphate
  • N-Acetylmuramic acid 6-phosphate
  • N-Acetylmuramic acid 6-phosphoric acid
Chemical Formula:C11H19NO11P
Weight:Average: 372.2424
Monoisotopic: 372.069571967
InChI Key:METUMBUEJVSNMZ-NFSFVEDMSA-M
InChI:InChI=1S/C11H20NO11P/c1-4(10(15)16)22-9-7(12-5(2)13)11(17)23-6(8(9)14)3-21-24(18,19)20/h4,6-9,11,14,17H,3H2,1-2H3,(H,12,13)(H,15,16)(H2,18,19,20)/q+1/p-1/t4?,6-,7-,8-,9-,11?/m1/s1
CAS number:Not Available
IUPAC Name:2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-oxidoethylidene)azaniumyl]-6-[(phosphono-λ³-oxidanyliumyl)methyl]oxan-4-yl]oxy}propanoate
Traditional IUPAC Name:2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-oxidoethylidene)ammonio]-6-[(phosphono-λ³-oxidanyliumyl)methyl]oxan-4-yl]oxy}propanoate
SMILES:[H]C(C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(C[O+]P(O)(O)=O)OC([H])(O)[C@]1([H])[NH+]=C(C)[O-])C([O-])=O
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility9.93 g/LALOGPS
logP0.77ALOGPS
logP-5.5ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)-7.7ChemAxon
pKa (Strongest Basic)1.46ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area202.84 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.35 m³·mol⁻¹ChemAxon
Polarizability31.49 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
1,6-anhydro-<i>N</i>-acetylmuramic acid recyclingPW002064 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:
  • 1,6-anhydro-N-acetylmuramic acid recycling PWY0-1261
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ac0-2149000000-35a0f2ff4ed7e829b76aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ly9-1094000000-3baae3a6a20cb02572f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2190000000-d57dead8972f6de7f01eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-6195000000-84cb7ad0e3a96d54d477View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9214000000-c3b570583127f7df5322View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9000000000-dee6f327b51e01128f7eView in MoNA
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID47968
HMDB IDNot Available
Pubchem Compound ID25202911
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-881
EcoCyc IDCPD0-881

Enzymes

General function:
Involved in carbon-oxygen lyase activity
Specific function:
Specifically catalyzes the cleavage of the D-lactyl ether substituent of MurNAc 6-phosphate, producing GlcNAc 6- phosphate and D-lactate. Is required for growth on MurNAc as the sole source of carbon and energy. Together with AnmK, is also required for the utilization of anhydro-N-acetylmuramic acid (anhMurNAc) either imported from the medium or derived from its own cell wall murein, and thus plays a role in cell wall recycling
Gene Name:
murQ
Uniprot ID:
P76535
Molecular weight:
31220
Reactions
N-acetylmuramate 6-phosphate + H(2)O = N-acetyl-D-glucosamine 6-phosphate + D-lactate.
General function:
Involved in ATP binding
Specific function:
Catalyzes the specific phosphorylation of 1,6-anhydro-N- acetylmuramic acid (anhMurNAc) with the simultaneous cleavage of the 1,6-anhydro ring, generating MurNAc-6-P. Is required for the utilization of anhMurNAc either imported from the medium or derived from its own cell wall murein, and thus plays a role in cell wall recycling
Gene Name:
anmK
Uniprot ID:
P77570
Molecular weight:
39496
Reactions
ATP + 1,6-anhydro-N-acetyl-beta-muramate + H(2)O = ADP + N-acetylmuramate 6-phosphate.