Record Information
Version2.0
Creation Date2012-05-31 14:32:54 -0600
Update Date2015-09-17 15:41:49 -0600
Secondary Accession Numbers
  • ECMDB20202
Identification
Name:UDP-N-Acetyl-D-mannosamine
DescriptionUDP-N-acetyl-D-mannosamine 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-Acetylmannosamine
  • UDP-ManNAc
  • Uridine 5'-(trihydrogen diphosphate), P'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester
  • Uridine 5'-(trihydrogen diphosphate), p'-(2-(acetylamino)-2-deoxy-a-D-mannopyranosyl) ester
  • Uridine 5'-(trihydrogen diphosphate), P'-(2-(acetylamino)-2-deoxy-alpha-D-mannopyranosyl) ester
  • Uridine 5'-(trihydrogen diphosphate), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-a-D-mannopyranosyl) ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-alpha-D-mannopyranosyl) ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-(2-(acetylamino)-2-deoxy-α-D-mannopyranosyl) ester
  • Uridine diphosphate N-acetylmannosamine
  • Uridine diphosphate N-acetylgalactosamine
  • Uridine diphosphate N-acetylmannosamine
  • Uridine diphosphoric acid N-acetylgalactosamine
  • Uridine diphosphoric acid N-acetylmannosamine
  • Uridine diphosphoric acid n-acetylmannosamine
  • Uridine-diphosphate-n-acetylgalactosamine
  • Uridine-diphosphate-n-acetylglucosamine
  • Uridine-diphosphoric acid-N-acetylgalactosamine
  • Uridine-diphosphoric acid-N-acetylglucosamine
Chemical Formula:C17H27N3O17P2
Weight:Average: 607.3537
Monoisotopic: 607.081569477
InChI Key:LFTYTUAZOPRMMI-IUPDHGCPSA-N
InChI:InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10+,11-,12-,13-,14-,15-,16?/m0/s1
CAS number:26575-17-7
IUPAC Name:N-[(3S,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)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
Traditional IUPAC Name:N-[(3S,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]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
SMILES:CC(=O)N[C@@H]1[C@H](O)[C@@H](O)[C@H](CO)OC1OP(O)(=O)OP(O)(=O)OC[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)N1C=CC(=O)NC1=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 phosphate
  • Pentose-5-phosphate
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Vinylogous amide
  • Acetamide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Urea
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility13 g/LALOGPS
logP-1.7ALOGPS
logP-4.1ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area307.39 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity118.4 m³·mol⁻¹ChemAxon
Polarizability50.85 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IPW000886 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
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, Positivesplash10-03di-0910020000-206daff4fcbabb7000d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2921000000-3efb6b3d3ace54161746View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4910000000-d0a8fca3f7775cdc5311View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08g3-9701421000-d26c8c8dc5ec960bdab6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03ec-9816010000-3f9697b8af62bee7f837View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r6-5911000000-043658d246494379ca6dView 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16287
HMDB IDHMDB13112
Pubchem Compound ID449043
Kegg IDC01170
ChemSpider ID395672
Wikipedia IDNot Available
BioCyc IDUDP-MANNAC
EcoCyc IDUDP-MANNAC

Enzymes

General function:
Involved in UDP-N-acetylglucosamine 2-epimerase activity
Specific function:
Catalyzes the reversible epimerization at C-2 of UDP-N- acetylglucosamine (UDP-GlcNAc) and thereby provides bacteria with UDP-N-acetylmannosamine (UDP-ManNAc), the activated donor of ManNAc residues. Also involved in bacteriophage N4 adsorption
Gene Name:
wecB
Uniprot ID:
P27828
Molecular weight:
42244
Reactions
UDP-N-acetyl-D-glucosamine = UDP-N-acetyl-D-mannosamine.
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.