Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110516
Identification
Name: UDP-N-acetyl-α-D-glucosamine-enolpyruvate
Description:A UDP-N-acetyl-3-O-(1-carboxylatovinyl)-D-glucosamine(3−) in which the anomeric centre of the glucosamine fragment has α-configuration.
Structure
Thumb
Synonyms:
  • UDP-N-acetyl-3-O-(1-carboxyvinyl)-α-D-glucosamine
  • UDP-N-acetyl-α-D-glucosamine-3-O-pyruvate ether
  • UDP-N-acetyl-3-(1-carboxyvinyl)-α-D-glucosamine
  • UDP-GlcNAc-pyruvate enol ether
  • UDP-GlcNAc-enolpyruvate
Chemical Formula: C20H26N3O19P2
Average Molecular Weight: 674.38
Monoisotopic Molecular Weight: 677.0870487864
InChI Key: BEGZZYPUNCJHKP-DBYWSUQTSA-K
InChI: InChI=1S/C20H29N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/p-3/t9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1
CAS number: Not Available
IUPAC Name:uridine 5'-{3-[2-acetamido-3-O-(1-carboxylatoethenyl)-2-deoxy-α-D-glucopyranosyl] diphosphate}
Traditional IUPAC Name: Not Available
SMILES:C=C(OC3(C(O)C(CO)OC(OP(=O)([O-])OP(=O)([O-])OCC1(OC(C(O)C(O)1)N2(C=CC(=O)NC(=O)2)))C(NC(C)=O)3))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
  • Pentose-5-phosphate
  • Pentose phosphate
  • N-acyl-alpha-hexosamine
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Pyrimidone
  • Sugar acid
  • Oxane
  • Pyrimidine
  • Phosphoric acid ester
  • Hydropyrimidine
  • Alkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Acetamide
  • Vinylogous amide
  • Tetrahydrofuran
  • Lactam
  • Urea
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Alcohol
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
  • a UDP-sugar (UDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE)
Physical Properties
State: Not Available
Charge:-3
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Molecular Weight674.378 g/molPubChem
XLogP3-AA-5.1 PubChem
Hydrogen Bond Donor Count6 PubChem
Hydrogen Bond Acceptor Count19 PubChem
Rotatable Bond Count12 PubChem
Exact Mass674.064 g/molPubChem
Monoisotopic Mass674.064 g/molPubChem
Topological Polar Surface Area335 A^2PubChem
Heavy Atom Count44 PubChem
Formal Charge-3 PubChem
Complexity1260 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count9 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
ChEBI68483
IAF126044212
KEGGC04631
PubChem25244881