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Record Information
Version	2.0
Creation Date	2012-05-31 14:48:38 -0600
Update Date	2015-06-03 17:20:08 -0600
Secondary Accession Numbers	ECMDB20518
Identification
Name:	N-Acetylmuramate 6-phosphate
Description	MurNAC-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xab7768ec> Close
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
Description	belongs to the class of organic compounds 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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	N-acyl-alpha-hexosamines
Alternative Parents	Hexose phosphates Monosaccharide phosphates Sugar acids and derivatives Monoalkyl phosphates Oxanes Secondary alcohols Hemiacetals Carboxylic acid salts Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Monocarboxylic acids and derivatives Dialkyl ethers Carboxylic acids Carboximidic acids and derivatives Organopnictogen compounds Organonitrogen compounds Organic zwitterions Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Muramic_acid Hexose phosphate N-acyl-alpha-hexosamine Monosaccharide phosphate Monoalkyl phosphate Sugar acid Alkyl phosphate Phosphoric acid ester Oxane Organic phosphoric acid derivative Monosaccharide Secondary alcohol Hemiacetal Carboxylic acid salt Oxacycle Organoheterocyclic compound Organic 1,3-dipolar compound Propargyl-type 1,3-dipolar organic compound Monocarboxylic acid or derivatives Ether Dialkyl ether Carboxylic acid Carboxylic acid derivative Carboximidic acid derivative Organic nitrogen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Organic salt Organic zwitterion Organonitrogen compound Carbonyl group Alcohol Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 9.93 g/L ALOGPS logP 0.77 ALOGPS logP -5.5 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) -7.7 ChemAxon pKa (Strongest Basic) 1.46 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 11 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 202.84 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 106.35 m³·mol⁻¹ ChemAxon Polarizability 31.49 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	N-Acetylmuramate 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid anhydro-n-acetylmuramic acid + Adenosine triphosphate + Water > N-Acetylmuramate 6-phosphate + ADP + Hydrogen ion
SMPDB Pathways:	1,6-anhydro-<i>N</i>-acetylmuramic acid recycling PW002064
KEGG Pathways:	Not Available
EcoCyc Pathways:	1,6-anhydro-N-acetylmuramic acid recycling PWY0-1261
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0ac0-2149000000-35a0f2ff4ed7e829b76a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0ly9-1094000000-3baae3a6a20cb02572f4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-2190000000-d57dead8972f6de7f01e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-6195000000-84cb7ad0e3a96d54d477 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9214000000-c3b570583127f7df5322 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-056r-9000000000-dee6f327b51e01128f7e View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID 47968 HMDB ID Not Available Pubchem Compound ID 25202911 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID CPD0-881 EcoCyc ID CPD0-881

Enzymes