Record Information
Version2.0
Creation Date2012-07-30 14:55:15 -0600
Update Date2015-06-03 17:21:06 -0600
Secondary Accession Numbers
  • ECMDB21294
Identification
Name:UDP-N-Acetyl-D-mannosaminouronate
DescriptionUDP-n-acetyl-D-mannosaminouronate 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
Synonyms:
  • UDP-N-acetyl-D-mannosaminouronate
  • UDP-N-acetyl-D-mannosaminouronic-acid
  • UDP-N-acetyl-mannosaminouronic acid
  • UDP-ManNAcA
  • UDP-ManNAcUA
  • UDP-N-Acetyl-2-amino-2-deoxy-D-mannuronate
  • UDP-N-Acetyl-2-amino-2-deoxy-D-mannuronic acid
  • UDP-N-Acetyl-D-mannosaminouronate
  • UDP-N-Acetyl-D-mannosaminouronic acid
  • UDP-N-Acetyl-D-mannosaminouronic-acid
  • UDP-N-Acetyl-D-mannosaminuronate
  • UDP-N-Acetyl-D-mannosaminuronic acid
  • UDP-N-Acetyl-mannosaminouronate
  • UDP-N-Acetyl-mannosaminouronic acid
  • Uridine 5'-[3-(2-acetamido-2-deoxy-D-mannopyranosyluronate) dihydrogen diphosphate]
  • Uridine 5'-[3-(2-acetamido-2-deoxy-D-mannopyranosyluronic acid) dihydrogen diphosphate]
  • Uridine 5'-[3-(2-acetamido-2-deoxy-D-mannopyranosyluronic acid) dihydrogen diphosphoric acid]
Chemical Formula:C17H22N3O18P2
Weight:Average: 618.3134
Monoisotopic: 618.037358939
InChI Key:DZOGQXKQLXAPND-XHUKORKBSA-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/t6-,8+,9-,10-,11+,12-,13+,14-,16-/m1/s1
CAS number:Not Available
IUPAC Name:(2S,3S,4R,5S,6R)-6-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4-dihydroxy-5-[(1-oxidoethylidene)amino]oxane-2-carboxylate
Traditional IUPAC Name:(2S,3S,4R,5S,6R)-6-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3,4-dihydroxy-5-[(1-oxidoethylidene)amino]oxane-2-carboxylate
SMILES:[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(C([O-])=O)[C@@]([H])(O)[C@]([H])(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
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:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility29.3 g/LALOGPS
logP-1.1ALOGPS
logP-3.8ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area332.95 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity150.21 m³·mol⁻¹ChemAxon
Polarizability49.78 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Amino sugar and nucleotide sugar metabolism ec00520
EcoCyc Pathways:
  • enterobacterial common antigen biosynthesis ECASYN-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-0e0dc83d33c048f828f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0001009000-d57e00c9bf5410d64e0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fkc-9850106000-59521796cef414ebc854View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-8900015000-9f5688b0f34abec1f175View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bi-9300001000-ff63898b04a88af06a61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7l-9500000000-e8308eea3a24b03201edView in MoNA
References
References:
  • 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 ID28581
HMDB IDNot Available
Pubchem Compound ID25246192
Kegg IDC06240
ChemSpider ID26331255
Wikipedia IDNot Available
BioCyc IDUDP-MANNACA
EcoCyc IDUDP-MANNACA

Enzymes

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.
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the synthesis of Und-PP-GlcNAc-ManNAcA (Lipid II), the second lipid-linked intermediate involved in ECA synthesis
Gene Name:
wecG
Uniprot ID:
P27836
Molecular weight:
27928
Reactions
UDP-ManNAcA + Und-PP-GlcNAc = UDP + Und-PP-GlcNAc-ManNAcA.