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1,6-Anhydro-N-acetyl-beta-muramate (M2MDB003610)

Record Information
Version2.0
Creation Date2012-10-10 12:22:38 -0600
Update Date2015-10-15 16:14:24 -0600
Secondary Accession Numbers
  • ECMDB23220
Identification
Name:1,6-Anhydro-N-acetyl-beta-muramate
Description1,6-Anhydro-N-acetyl-beta-muramate monocarboxylic a obtained by removal of a proton from the carboxy group of 1,6-anhydro-N-acetyl-beta-muramic acid. It is a substrate of the enzyme anhydro-N-acetylmuramic acid kinase. The reaction it catalyzes is: ATP + 1,6-anhydro-N-acetyl-beta-muramate + H2O = ADP + N-acetylmuramate 6-phosphate. This enzyme, along with EC 4.2.1.126 (N-acetylmuramic acid 6-phosphate etherase) is required for the utilization of anhydro-N-acetylmuramic acid in proteobacteria. The substrate is either imported from the medium or derived from the bacterium's own cell wall murein during cell wall recycling. The product N-acetylmuramate 6-phosphate is produced as a 7:1 mixture of the α- and β-anomers.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (2R)-2-(1R,2S,3R,4R,5R)-4-acetamido-2-Hydroxy-6,8-dioxabicyclo3.2.1octan-3-yloxypropanoate
  • (2R)-2-(1R,2S,3R,4R,5R)-4-acetamido-2-hydroxy-6,8-dioxabicyclo3.2.1octan-3-yloxypropanoic acid
  • (2R)-2-{(1R,2S,3R,4R,5R)-4-(acetylamino)-2-hydroxy-6,8-dioxabicyclo3.2.1oct-3-yloxy}propanoate
  • (2R)-2-{(1R,2S,3R,4R,5R)-4-(acetylamino)-2-hydroxy-6,8-dioxabicyclo3.2.1oct-3-yloxy}propanoic acid
  • (2R)-2-{(1R,2S,3R,4R,5R)-4-acetamido-2-hydroxy-6,8-dioxabicyclo3.2.1oct-3-yloxy}propanoate (non-preferred name)
  • (2R)-2-{(1R,2S,3R,4R,5R)-4-Acetamido-2-hydroxy-6,8-dioxabicyclo3.2.1oct-3-yloxy}propanoic acid (non-preferred name)
  • 1,6-anhMurNAc
  • 1,6-anhydro-N-Acetyl-b-muramate
  • 1,6-anhydro-N-Acetyl-b-muramic acid
  • 1,6-anhydro-N-Acetyl-beta-muramic acid
  • 1,6-anhydro-N-Acetyl-muramate
  • 1,6-anhydro-N-acetyl-muramic acid
  • 1,6-anhydro-N-Acetyl-β-muramate
  • 1,6-anhydro-N-Acetyl-β-muramic acid
  • 1,6-anhydro-N-Acetylmuramate
  • 1,6-anhydro-N-acetylmuramic acid
  • 2-(2-acetylamino-4-HYDROXY-6,8-dioxa-bicyclo3.2.1oct-3-yloxy)-propionate
  • 2-(2-ACETYLAMINO-4-HYDROXY-6,8-DIOXA-BICYCLO3.2.1OCT-3-YLOXY)-PROPIONIC ACID
Chemical Formula:C11H16NO7
Weight:Average: 274.2472
Monoisotopic: 274.092676871
InChI Key:ZFEGYUMHFZOYIY-YVNCZSHWSA-M
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)/p-1/t4-,6-,7-,8-,9-,11-/m1/s1
CAS number:Not Available
IUPAC Name:(2R)-2-{[(1R,2S,3R,4R,5R)-4-acetamido-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}propanoic acid
Traditional IUPAC Name:1,6-anhMurNAc
SMILES:C[C@@H](O[C@H]1[C@H](O)[C@H]2CO[C@H](O2)[C@@H]1N=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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxepanes
Sub ClassNot Available
Direct ParentOxepanes
Alternative Parents
Substituents
  • Oxepane
  • Monosaccharide
  • Oxane
  • Meta-dioxolane
  • Acetamide
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility155 g/LALOGPS
logP-1ALOGPS
logP-1.4ChemAxon
logS-0.25ALOGPS
pKa (Strongest Acidic)3.56ChemAxon
pKa (Strongest Basic)-0.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity58.84 m³·mol⁻¹ChemAxon
Polarizability25.32 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + 1,6-Anhydro-N-acetyl-beta-muramate + Water > ADP + N-Acetylmuramic acid 6-phosphate
Adenosine triphosphate + 1,6-Anhydro-N-acetyl-beta-muramate + Water <> ADP + N-Acetylmuramic acid 6-phosphate
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, Positivesplash10-056r-1090000000-2ff231550860c6db908fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ly9-3690000000-c88a4f0e594fdba80454View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03du-7900000000-5de96d4bac6816a42738View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1090000000-fc66c2f2492bfc79b7dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-3490000000-fa17abad175b9a761b74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9600000000-4629bad1f36616a5412bView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID40666
HMDB IDNot Available
Pubchem Compound ID6602346
Kegg IDC19769
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoAH0

Enzymes

Protein Details
1. Anhydro-N-acetylmuramic acid kinase
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.