UDP-2-acetamido-2-deoxy-α-D-ribo-hex-3-uluronate (PAMDB120559)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120559
Identification
Name: UDP-2-acetamido-2-deoxy-α-D-ribo-hex-3-uluronate
Description:A nucleotide-sugar oxoanion obtained via deprotonation of the diphosphate and carboxy OH groups of UDP-2-acetamido-2-deoxy-α-D-ribo-hex-3-uluronic acid; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • UDP-2-acetamido-2-deoxy-α-D-ribo-hex-3-uluronate
  • UDP-3-keto-α-D-GlcNAcA (3−)
  • UDP-α-GlcNAc(3keto)A(3−)
  • UDP-GlcNAc(3keto)A(3−)
Chemical Formula: C17H20N3O18P2
Average Molecular Weight: 616.302
Monoisotopic Molecular Weight: 619.04517
InChI Key: FQYJGWJSECSVLP-AZKAKUJRSA-K
InChI:InChI=1S/C17H23N3O18P2/c1-5(21)18-8-10(24)11(25)13(15(27)28)36-16(8)37-40(32,33)38-39(30,31)34-4-6-9(23)12(26)14(35-6)20-3-2-7(22)19-17(20)29/h2-3,6,8-9,11-14,16,23,25-26H,4H2,1H3,(H,18,21)(H,27,28)(H,30,31)(H,32,33)(H,19,22,29)/p-3/t6-,8-,9-,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)=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
  • Pentose-5-phosphate
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Pyrimidone
  • Beta-hydroxy acid
  • Organic phosphoric acid derivative
  • Pyran
  • Oxane
  • Alkyl phosphate
  • Hydroxy acid
  • Phosphoric acid ester
  • Pyrimidine
  • Hydropyrimidine
  • Monosaccharide
  • Acetamide
  • Vinylogous amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Carboxamide group
  • Ketone
  • Lactam
  • Cyclic ketone
  • Urea
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-3
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Mass616.2970ChemAxon
logP-4.4168ChemAxon
H-bond acceptors21ChemAxon
H-bond donors5ChemAxon
Rotatable bonds11ChemAxon
PSA347.8800ChemAxon
RO5 violations2ChemAxon
RO3 violations5ChemAxon
Refractivity114.5683ChemAxon
Atoms60ChemAxon
Rings3ChemAxon
Heavy atoms40ChemAxon
Hydrogen atoms20ChemAxon
Heteroatoms23ChemAxon
N/O atoms21ChemAxon
Inorganic atoms0ChemAxon
Halogen atoms0ChemAxon
Chiral centers8ChemAxon
R/S chiral centers0ChemAxon
Unknown chiral centers0ChemAxon
Undefined chiral centers8ChemAxon
Stereo double bonds0ChemAxon
Cis/trans stereo double bonds0ChemAxon
Unknown stereo double bonds0ChemAxon
Undefined stereo double bonds 0ChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
UDP-N-acetyl-α-D-glucosaminouronate + NAD+ → UDP-2-acetamido-2-deoxy-α-D-ribo-hex-3-uluronate + NADH + 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:
    • Thoden JB, Holden HM (2010)Structural and functional studies of WlbA: A dehydrogenase involved in the biosynthesis of 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid . Biochemistry 49, Pubmed: 20690587
    • 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
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    CHEBI62250