Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000649
Name: UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate
Description:UDP-n-acetylmuramoyl-L-alanyl-D-glutamate is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. UDP-N-acetylmuramoyl-L-alanyl-D-glutamate is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. UDP-N-acetylmuramoyl-L-alanyl-D-glutamate:meso-diaminopimelate ligase is a cytoplasmic enzyme that catalyzes the addition of meso-diaminopimelic acid to nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate in the biosynthesis of bacterial cell-wall peptidoglycan. (PMID 11124264)
  • UDP-GlcNAcMurAlaGlu
  • UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate tetraanion
  • UDP-N-Acetylmuramoyl-L-alanyl-D-glutamic acid
  • UDP-N-Acetylmuramoyl-L-alanyl-D-glutamic acid tetraanion
  • Uridine 5'-(3-{2-acetamido-2-deoxy-3-O-[(2R)-1-{[(2S)-1-D-glutamato-1-oxopropan-2-yl]amino}-1-oxopropan-2-yl]-D-glucopyranosyl} diphosphate)
  • Uridine 5'-(3-{2-acetamido-2-deoxy-3-O-[(2R)-1-{[(2S)-1-D-glutamato-1-oxopropan-2-yl]amino}-1-oxopropan-2-yl]-D-glucopyranosyl} diphosphoric acid)
Chemical Formula: C22H32Cl2N2O4
Average Molecular Weight: 459.41
Monoisotopic Molecular Weight: 458.1739129
CAS number: 17088-64-1
IUPAC Name:(2R)-2-({2-[(2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)pentanedioic acid
Traditional IUPAC Name: (2R)-2-({2-[(2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)pentanedioic acid
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Pyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct Parent Pyrimidine nucleotide sugars
Alternative Parents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Alpha peptide
  • N-acyl-alpha-hexosamine
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Glucosamine
  • Amino sugar
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Alpha-amino acid or derivatives
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Amino saccharide
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility7.58 mg/mLALOGPS
pKa (Strongest Acidic)1.72ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area436.17 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity180.16 m3·mol-1ChemAxon
Polarizability76.89 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0920000030-9501bc6942335865a32bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1910000000-081da383d328cda7011bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3910000000-47d3cd7d61b410b044d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-7902600380-4e6fc4dba489cd21009dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ec-6914104040-1d9c3c55962ac034be03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-4923000000-36be71bdb3f634865e8dView in MoNA
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
HMDB IDNot Available
Pubchem Compound ID23724464
Kegg IDC00692
ChemSpider ID388428
Wikipedia IDNot Available