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UDP-N-acetyl-α-D-mannosaminuronate (M2MDB006353)

Record Information
Version2.0
Creation Date2015-09-08 17:50:20 -0600
Update Date2015-09-14 16:46:42 -0600
Secondary Accession Numbers
  • ECMDB24236
Identification
Name:UDP-N-acetyl-α-D-mannosaminuronate
DescriptionUDP-N-acetyl-alpha-D-mannosaminuronate is an intermediate in several pathways in E.coli. In enterobacterial common antigen biosynthesis, it is a substrate for the enzyme UDP-N-acetyl-D-mannosaminuronic acid transferase which catalyzes the reaction N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol + UDP-N-acetyl-alpha-D-mannosaminuronate -> N-acetyl-β-D-mannosaminuronyl-(1→4)-N-acetyl-alpha-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol + UDP + H+. It is also a product for enzyme UDP-N-acetyl-D-mannosamine dehydrogenase which catalyzes reaction UDP-N-acetyl-alpha-D-mannosamine + 2 NAD+ + H2O -> UDP-N-acetyl-alpha-D-mannosaminuronate + 2 NADH + 3 H+ in UDP-N-acetyl-α-D-mannosaminouronate biosynthesis pathway (BioCyc compound: UDP-MANNACA).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • UDP-N-Acetyl-α-D-mannosaminuronic acid
Chemical Formula:C17H22N3O18P2
Weight:Average: 618.315
Monoisotopic: 618.039005616
InChI Key:DZOGQXKQLXAPND-UHFFFAOYSA-K
InChI:InChI=1S/C17H25N3O18P2/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/h2-3,6,8-14,16,23-26H,4H2,1H3,(H,18,21)(H,27,28)(H,30,31)(H,32,33)(H,19,22,29)/p-3
CAS number:Not Available
IUPAC Name:6-{[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}-5-acetamido-3,4-dihydroxyoxane-2-carboxylate
Traditional IUPAC Name:6-[({[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]-5-acetamido-3,4-dihydroxyoxane-2-carboxylate
SMILES:CC(=O)NC1C(O)C(O)C(OC1OP([O-])(=O)OP([O-])(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O)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
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Beta-hydroxy acid
  • Pyrimidone
  • Hydropyrimidine
  • Phosphoric acid ester
  • Pyran
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Monosaccharide
  • Pyrimidine
  • Tetrahydrofuran
  • Vinylogous amide
  • Acetamide
  • Heteroaromatic compound
  • Carboxamide group
  • Lactam
  • Urea
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen 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 Solubility28.1 g/LALOGPS
logP-1.2ALOGPS
logP-5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area325.97 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity126.02 m³·mol⁻¹ChemAxon
Polarizability50.41 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
UDP-N-acetyl-D-mannosamine + 2 NAD + Water + UDP-N-Acetyl-D-mannosamine > UDP-N-acetyl-α-D-mannosaminuronate +2 NADH +3 Hydrogen ion
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IPW000886 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, Positivesplash10-014i-0000009000-9e19a1bd1aebcf232377View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0001009000-f889b0a64a9bd8b485bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03du-9760001000-119b728f2599bc3df927View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-7900015000-9c14a583c811f90b8ab2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ko-9100001000-9b63a8c977b48982afabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-5f490bbde2dfe402766eView 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-acetyl-D-mannosamine dehydrogenase
General function:
Involved in oxidation-reduction process
Specific function:
Catalyzes the four-electron oxidation of UDP-N-acetyl-D- mannosamine (UDP-ManNAc), reducing NAD(+) and releasing UDP-N- acetylmannosaminuronic acid (UDP-ManNAcA)
Gene Name:
wecC
Uniprot ID:
P27829
Molecular weight:
45838
Reactions
UDP-N-acetyl-D-mannosamine + 2 NAD(+) + H(2)O = UDP-N-acetyl-D-mannosaminuronate + 2 NADH.