UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine (PAMDB000647)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000647
Identification
Name: UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine
Description:UDP-n-acetyl-3-(1-carboxyvinyl)-D-glucosamine is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Enolpyruvyl-UDP-N-acetylglucosamine
  • EP-UDPGlCNAC
  • UDP-N-acetyl-3-(1-carboxyvinyl)-D-glucosamine
  • UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine
  • UDP-N-acetylglucosamine-3-O-pyruvate ether
  • UDP-GlcNAc-enolpyruvate
  • UDP-GlcNAc-enolpyruvic acid
  • UDP-GlcNAc-pyruvate enol ether
  • UDP-GlcNAc-pyruvic acid enol ether
  • UDP-GlcNacPyrEE
  • UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine
  • UDP-N-Acetyl-3-O-(1-carboxyvinyl)-D-glucosamine
  • UDP-N-Acetylenolpyruvylglucosamine
  • UDP-N-Acetylglucosamine enolpyruvate
  • UDP-N-Acetylglucosamine enolpyruvic acid
  • UDP-N-Acetylglucosamine-3-O-pyruvate ether
  • UDP-N-Acetylglucosamine-3-O-pyruvateether
  • UDP-N-Acetylglucosamine-3-O-pyruvic acid ether
  • UdPGNAC-enolpyruvate
  • UdPGNAC-enolpyruvic acid
  • UNAGEP
Chemical Formula: C20H29N3O19P2
Average Molecular Weight: 677.4005
Monoisotopic Molecular Weight: 677.087048785
InChI Key: BEGZZYPUNCJHKP-DBYWSUQTSA-N
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)/t9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1
CAS number: 70222-94-5
IUPAC Name:2-{[(2R,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}prop-2-enoic acid
Traditional IUPAC Name: 2-{[(2R,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}prop-2-enoic acid
SMILES:[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(OC(=C)C(O)=O)[C@@]2([H])N=C(C)O)O[C@@]([H])(N2C=CC(O)=NC2=O)[C@]([H])(O)[C@]1([H])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
  • N-acyl-alpha-hexosamine
  • Glucosamine
  • Amino sugar
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Amino saccharide
  • Sugar acid
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • 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
  • UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine (CHEBI:68507 )
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility18.6 mg/mLALOGPS
logP-1.3ALOGPS
logP-3.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area333.69 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity134.15 m3·mol-1ChemAxon
Polarizability56.58 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine <> Phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine
Hydrogen ion + NADPH + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine <> NADP + UDP-N-Acetylmuraminate
UDP-N-Acetylmuraminate + NAD <> UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADH + Hydrogen ion
Phosphoenolpyruvic acid + Uridine diphosphate-N-acetylglucosamine > Inorganic phosphate + UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine
UDP-N-Acetylmuraminate + NADP > UDP-N-Acetyl-3-(1-carboxyvinyl)-D-glucosamine + NADPH
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910003000-11c12eaadbbfd5b5e021View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2911000000-b27da2682655d5af483dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4910000000-f2fcc76c834ceb1b1bc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-9842417000-d8491df474af1bf680a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06r6-9803402000-7d2fde68c6bad3fbc412View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r6-5912000000-344fcfd8dfc9853678dfView in MoNA
References
References:
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16435
HMDB IDNot Available
Pubchem Compound ID172502
Kegg IDC04631
ChemSpider ID10128141
Wikipedia IDNot Available
BioCyc IDUDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE
EcoCyc IDUDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE
Ligand ExpoEPU