UDP-N-acetyl-α-D-glucosamine-enolpyruvate (ECMDB24237) (M2MDB006354)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:50:20 -0600
Update Date2015-09-14 16:46:42 -0600
Secondary Accession Numbers
  • ECMDB24237
Identification
Name:UDP-N-acetyl-α-D-glucosamine-enolpyruvate
DescriptionUDP-N-acetyl-alpha-D-glucosamine-enolpyruvate is an intermediate in UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-DAP-containing) pathway in E.coli. It is a substrate for the enzyme UDP-N-acetylenolpyruvoylglucosamine reductase which catalyzes the reaction UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate + NADPH + H+ -> UDP-N-acetyl-alpha-D-muramate + NADP+. It is also a product for enzyme UDP-N-acetylglucosamine enolpyruvoyl transferase which catalyzes reaction UDP-N-acetyl-alpha-D-glucosamine + phosphoenolpyruvate -> UDP-N-acetyl-α-D-glucosamine-enolpyruvate + phosphate (BioCyc compound: UDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • UDP-N-Acetyl-α-D-glucosamine-enolpyruvic acid
Chemical Formula:C20H26N3O19P2
Weight:Average: 674.379
Monoisotopic: 674.065220365
InChI Key:BEGZZYPUNCJHKP-UHFFFAOYSA-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
CAS number:Not Available
IUPAC Name:2-[(2-{[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy]prop-2-enoate
Traditional IUPAC Name:2-({2-[({[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)prop-2-enoate
SMILES:CC(=O)NC1C(OP([O-])(=O)OP([O-])(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)OC(CO)C(O)C1OC(=C)C([O-])=O
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility16.7 g/LALOGPS
logP-0.98ALOGPS
logP-4.6ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area335.2 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity141.9 m³·mol⁻¹ChemAxon
Polarizability55.43 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Uridine diphosphate-N-acetylglucosamine + Phosphoenolpyruvic acid > Phosphate + UDP-N-acetyl-α-D-glucosamine-enolpyruvate
UDP-N-acetyl-α-D-glucosamine-enolpyruvate + NADPH + Hydrogen ion + NADPH > NADP + UDP-N-acetyl-α-D-muramate
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IPW000886 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis IPW000906 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-c7038eb4ed6123137d5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1001009000-0a0565ac6231b8e384b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9421003000-8a3b2c5ad565ff610ca7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-7000009000-2144809f24d0816ffe51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-9100003000-25052929b8f62b948432View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9300000000-d989f93239b8508b2014View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. UDP-N-acetylenolpyruvoylglucosamine reductase
General function:
Involved in flavin adenine dinucleotide binding
Specific function:
Cell wall formation
Gene Name:
murB
Uniprot ID:
P08373
Molecular weight:
37851
Reactions
UDP-N-acetylmuramate + NADP(+) = UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine + NADPH.
Protein Details
2. UDP-N-acetylglucosamine 1-carboxyvinyltransferase
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Cell wall formation. Adds enolpyruvyl to UDP-N- acetylglucosamine. Target for the antibiotic phosphomycin
Gene Name:
murA
Uniprot ID:
P0A749
Molecular weight:
44817
Reactions
Phosphoenolpyruvate + UDP-N-acetyl-D-glucosamine = phosphate + UDP-N-acetyl-3-O-(1-carboxyvinyl)-D-glucosamine.