Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001327
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 Pseudomonas aeruginosa, it can not serve as the sole source of carbon for growth.
Structure
Thumb
Synonyms:
  • 1,6-anhMurNAc
  • 1,6-Anhydro-N-acetylmuramate
  • 1,6-Anhydro-N-acetylmuramic acid
Chemical Formula: C11H17NO7
Average Molecular Weight: 275.2552
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as oxepanes. These 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 ClassOrganoheterocyclic compounds
Class Oxepanes
Sub ClassNot Available
Direct Parent Oxepanes
Alternative Parents
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
  • 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:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility45.4 mg/mLALOGPS
logP-0.62ALOGPS
logP-0.55ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)3.54ChemAxon
pKa (Strongest Basic)1.36ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.81 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.37 m3·mol-1ChemAxon
Polarizability25.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a7i-0090000000-d65769bdb2b625a1338fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-2590000000-363094b06f3083b70e4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ki-6910000000-552f488fd871ad624ebbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1090000000-3fb08bcd0c788dcadb4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-3490000000-7f2d261fd1517d8a2490View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9700000000-0a49ea8c6cf44dc9233bView 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 ID40666
HMDB IDNot Available
Pubchem Compound ID25201515
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-882
EcoCyc IDCPD0-882