Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110517
Identification
Name: UDP-N-acetyl-α-D-muramoyl-L-alanyl-D-glutamate
Description:Tetraanion of UDP-N-acetylmuramoyl-L-alanyl-D-glutamic acid arising from deprotonation of the diphosphate and glutamate carboxy groups; major species at pH 7.3.
Structure
Thumb
Synonyms:
  • UDP-N-acetyl-α-D-muramoyl-L-alanyl-D-glutamate 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)
Chemical Formula: C28H39N5O23P2
Average Molecular Weight: 875.58
Monoisotopic Molecular Weight: 879.1824057346
InChI Key: OJZCATPXPWFLHF-HPUCEMLMSA-J
InChI: InChI=1S/C28H43N5O23P2/c1-10(23(42)31-13(26(44)45)4-5-17(37)38)29-24(43)11(2)52-22-18(30-12(3)35)27(54-14(8-34)20(22)40)55-58(49,50)56-57(47,48)51-9-15-19(39)21(41)25(53-15)33-7-6-16(36)32-28(33)46/h6-7,10-11,13-15,18-22,25,27,34,39-41H,4-5,8-9H2,1-3H3,(H,29,43)(H,30,35)(H,31,42)(H,37,38)(H,44,45)(H,47,48)(H,49,50)(H,32,36,46)/p-4/t10-,11+,13+,14+,15+,18+,19+,20+,21+,22+,25+,27+/m0/s1
CAS number: Not Available
IUPAC Name:Not Available
Traditional IUPAC Name: Not Available
SMILES:CC(NC(=O)C(C)OC1(C(C(OC(C(O)1)CO)OP(=O)([O-])OP(=O)([O-])OCC2(OC(C(O)C(O)2)N3(C=CC(=O)NC(=O)3)))NC(C)=O))C(=O)NC(CCC([O-])=O)C(=O)[O-]
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
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Alpha-dipeptide
  • Alpha peptide
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-acyl-alpha-hexosamine
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Glycosyl compound
  • N-glycosyl compound
  • Alanine or derivatives
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyrimidone
  • Dicarboxylic acid or derivatives
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Vinylogous amide
  • Tetrahydrofuran
  • Acetamide
  • Heteroaromatic compound
  • Urea
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Ether
  • Carboxylic acid derivative
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Carboxylic acid
  • Primary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
  • a UDP-sugar (UDP-AA-GLUTAMATE)
Physical Properties
State: Not Available
Charge:-4
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Molecular Weight875.58 g/molPubChem
XLogP3-AA-6 PubChem
Hydrogen Bond Donor Count8 PubChem
Hydrogen Bond Acceptor Count23 PubChem
Rotatable Bond Count18 PubChem
Exact Mass875.151 g/molPubChem
Monoisotopic Mass875.151 g/molPubChem
Topological Polar Surface Area434 A^2PubChem
Heavy Atom Count58 PubChem
Formal Charge-4 PubChem
Complexity1670 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count12 PubChem
Undefined Atom Stereocenter Count0 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra: Not Available
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
ChEBI57968
IAF126035714
KEGGC00692
PubChem25243858