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Record Information
Version	2.0
Creation Date	2012-05-31 14:48:41 -0600
Update Date	2015-06-03 17:20:08 -0600
Secondary Accession Numbers	ECMDB20519
Identification
Name:	1,6-Anhydro-N-acetylmuramate
Description	1,6-anhMurNAC is an Amino Sugar. These are compounds having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. 1,6-anhydro-N-acetylmuramic acid (anhMurNAc) is one of the components of murein that is recycled inside the cell. Although exogenously provided anhMurNAc can be taken up by E. coli, it can not serve as the sole source of carbon for growth.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa4cec350> Close
Synonyms:	1,6-anhMurNAc 1,6-Anhydro-N-acetylmuramate 1,6-Anhydro-N-acetylmuramic acid
Chemical Formula:	C11H17NO7
Weight:	Average: 275.2552 Monoisotopic: 275.100501903
InChI Key:	ZFEGYUMHFZOYIY-NFSFVEDMSA-N
InChI:	InChI=1S/C11H17NO7/c1-4(10(15)16)18-9-7(12-5(2)13)11-17-3-6(19-11)8(9)14/h4,6-9,11,14H,3H2,1-2H3,(H,12,13)(H,15,16)/t4?,6-,7-,8-,9-,11?/m1/s1
CAS number:	Not Available
IUPAC Name:	2-{[(1R,2S,3R,4R)-2-hydroxy-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}propanoic acid
Traditional IUPAC Name:	2-{[(1R,2S,3R,4R)-2-hydroxy-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}propanoic acid
SMILES:	[H]C(C)(O[C@@]1([H])[C@]([H])(O)[C@@]2([H])COC([H])(O2)[C@]1([H])N=C(C)O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Oxepanes
Sub Class	Not Available
Direct Parent	Oxepanes
Alternative Parents	Oxanes Monosaccharides 1,3-dioxolanes Secondary alcohols Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Monocarboxylic acids and derivatives Dialkyl ethers Carboxylic acids Carboximidic acids Acetals Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Oxepane Oxane Monosaccharide Meta-dioxolane Secondary alcohol Oxacycle 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 Carboximidic acid Acetal Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Organooxygen compound Organonitrogen compound Carbonyl group Alcohol Aliphatic heteropolycyclic compound
Molecular Framework	Aliphatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 45.4 g/L ALOGPS logP -0.62 ALOGPS logP -0.55 ChemAxon logS -0.78 ALOGPS pKa (Strongest Acidic) 3.54 ChemAxon pKa (Strongest Basic) 1.36 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 117.81 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 59.37 m³·mol⁻¹ ChemAxon Polarizability 25.7 ų ChemAxon Number of Rings 2 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:	1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + 1,6-Anhydro-N-acetylmuramate 1,6-Anhydrous-N-Acetylmuramyl-tripeptide + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + 1,6-Anhydro-N-acetylmuramate N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid + Water > N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate 1,6-Anhydro-N-acetylmuramate + Adenosine triphosphate + Water > N-Acetylmuramic acid 6-phosphate + ADP + Hydrogen ion <i>N</i>-acetyl-&beta;-D-glucosamine(anhydrous)-<i>N</i>-acetylmuramate + Water N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate Adenosine triphosphate + Water + 1,6-Anhydro-N-acetylmuramate <> Adenosine diphosphate + MurNAc-6-P + ADP
SMPDB Pathways:	Amino sugar and nucleotide sugar metabolism III PW000895
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 GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a7i-0090000000-d65769bdb2b625a1338f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0f80-2590000000-363094b06f3083b70e4e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03ki-6910000000-552f488fd871ad624ebb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00di-1090000000-3fb08bcd0c788dcadb4b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0pc0-3490000000-7f2d261fd1517d8a2490 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0ab9-9700000000-0a49ea8c6cf44dc9233b View in MoNA MS Mass Spectrum (Electron Ionization) 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 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 40666 HMDB ID Not Available Pubchem Compound ID 25201515 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID CPD0-882 EcoCyc ID CPD0-882

Enzymes