UDP-2-acetamido-3-amino-2,3-dideoxy-α-D-glucuronate (PAMDB120579)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120579
Identification
Name: UDP-2-acetamido-3-amino-2,3-dideoxy-α-D-glucuronate
Description:A nucleotide-sugar oxoanion obtained via deprotonation of the diphosphate and carboxy OH groups and protonation of the primary amino group of UDP-2-acetamido-3-amino-2,3-dideoxy-α-D-glucuronic acid; major species at pH 7.3.
Structure
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🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2S,3S,4R,5R,6R)-5-(acetylamino)-4-ammonio-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}phosphinato)oxy]phosphinato}oxy)-3-hydroxytetrahydro-2H-pyran-2-carboxylate
  • UDP-2-acetamido-3-amino-2,3-dideoxy-α-D-glucuronate
  • UDP-2-acetamido-3-azaniumyl-2,3-dideoxy-α-D-glucuronate(2−)
  • UDP-GlcNAc3NA(2−)
Chemical Formula: C17H24N4O17P2
Average Molecular Weight: 618.341
Monoisotopic Molecular Weight: 621.08466
InChI Key: RRAQYLXLCYIZBB-HHKCBAECSA-L
InChI:InChI=1S/C17H26N4O17P2/c1-5(22)19-9-8(18)11(25)13(15(27)28)36-16(9)37-40(32,33)38-39(30,31)34-4-6-10(24)12(26)14(35-6)21-3-2-7(23)20-17(21)29/h2-3,6,8-14,16,24-26H,4,18H2,1H3,(H,19,22)(H,27,28)(H,30,31)(H,32,33)(H,20,23,29)/p-2/t6-,8-,9-,10-,11+,12-,13+,14-,16-/m1/s1
CAS number: Not Available
IUPAC Name:Not Available
Traditional IUPAC Name: Not Available
SMILES:CC(=O)NC1(C(C(C(C(=O)[O-])OC1OP([O-])(=O)OP([O-])(OCC3(OC(N2(C(NC(=O)C=C2)=O))C(O)C3O))=O)O)[N+])
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
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Beta-hydroxy acid
  • Pyrimidone
  • Hydropyrimidine
  • Hydroxy acid
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyran
  • Pyrimidine
  • Alkyl phosphate
  • Vinylogous amide
  • Acetamide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Urea
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Lactam
  • Carboxamide group
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic salt
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Mass618.3363ChemAxon
logP-2.3276ChemAxon
H-bond acceptors21ChemAxon
H-bond donors7ChemAxon
Rotatable bonds10ChemAxon
PSA357.7500ChemAxon
RO5 violations3ChemAxon
RO3 violations5ChemAxon
Refractivity119.7022ChemAxon
Atoms64ChemAxon
Rings3ChemAxon
Heavy atoms40ChemAxon
Hydrogen atoms24ChemAxon
Heteroatoms23ChemAxon
N/O atoms21ChemAxon
Inorganic atoms0ChemAxon
Halogen atoms0ChemAxon
Chiral centers9ChemAxon
R/S chiral centers9ChemAxon
Unknown chiral centers0ChemAxon
Undefined chiral centers0ChemAxon
Stereo double bonds1ChemAxon
Cis/trans stereo double bonds0ChemAxon
Unknown stereo double bonds1ChemAxon
Undefined stereo double bonds 0ChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
UDP-2-acetamido-3-amino-2,3-dideoxy-α-D-glucuronate + acetyl-CoA → UDP-2,3-diacetamido-2,3-dideoxy-α-D-glucuronate + coenzyme A + Hydrogen ion
UDP-2-acetamido-3-amino-2,3-dideoxy-α-D-glucuronate + alpha-Ketoglutarate → UDP-2-acetamido-2-deoxy-α-D-ribo-hex-3-uluronate + L-glutamate
Pathways:
  • UDP-2,3-diacetamido-2,3-dideoxy-α-D-mannuronate biosynthesisPWY-7090
    Spectra
    Spectra: Not Available
    References
    References:
    • Larkin A, Olivier NB, Imperiali B (2010)Structural analysis of WbpE from Pseudomonas aeruginosa PAO1: a nucleotide sugar aminotransferase involved in O-antigen assembly. Biochemistry 49, Pubmed: 20604544
    • Westman EL, Preston A, Field RA, Lam JS (2008)Biosynthesis of a rare di-N-acetylated sugar in the lipopolysaccharides of both Pseudomonas aeruginosa and Bordetella pertussis occurs via an identical scheme despite different gene clusters. Journal of bacteriology 190, Pubmed: 18621892
    • Westman EL, McNally DJ, Charchoglyan A, Brewer D, Field RA, Lam JS (2009)Characterization of WbpB, WbpE, and WbpD and reconstitution of a pathway for the biosynthesis of UDP-2,3-diacetamido-2,3-dideoxy-D-mannuronic acid in Pseudomonas aeruginosa. The Journal of biological chemistry 284, Pubmed: 19282284
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    CHEBI62245