UDP-N-acetyl-α-D-glucosamine (PAMDB110519)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110519
Identification
Name: UDP-N-acetyl-α-D-glucosamine
Description:Dianion of UDP-N-acetyl-α-D-glucosamine arising from deprotonation of both free diphosphate OH groups; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • UDP-acetyl-D-glucosamine
  • UDP-GlcNAc
  • UDP-N-acetyl-glucosamine
  • uridine diphosphate N-acetylglucosamine
  • N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
  • UDP-2-acetamido-2-deoxy-α-D-glucose
  • UDP-N-acetyl-D-glucosamine
  • UDP-α-N-acetyl-D-glucosamine
Chemical Formula: C17H25N3O17P2
Average Molecular Weight: 605.34
Monoisotopic Molecular Weight: 607.081569478
InChI Key: LFTYTUAZOPRMMI-CFRASDGPSA-L
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)/p-2/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
CAS number: 528-04-1
IUPAC Name:uridine 5'-[3-(acetamido-2-deoxy-α-D-glucopyranosyl) diphosphate]
Traditional IUPAC Name: udp-N-acetyl-?-D-glucosamine
SMILES:CC(NC3(C(OP(OP(OCC1(C(C(C(O1)N2(C=CC(NC2=O)=O))O)O))([O-])=O)([O-])=O)OC(C(C3O)O)CO))=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct Parent Pyrimidine 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
  • Oxane
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Hydropyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Acetamide
  • Oxolane
  • Vinylogous amide
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Urea
  • Lactam
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.4 mg/mLALOGPS
logP-1.4ALOGPS
logP-5.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area300.41 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.56 m3·mol-1ChemAxon
Polarizability50.35 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
UDP-N-acetyl-α-D-glucosamine + Water → N-acetyl-α-D-mannosamine + UDP + Hydrogen ion
UDP-N-acetyl-α-D-glucosamine + NAD+ + Water → UDP-N-acetyl-α-D-glucosaminouronate + NADH + Hydrogen ion
decaprenyl-diphospho-N-acetylmuramoyl-pentapeptide + UDP-N-acetyl-α-D-glucosamine → Hydrogen ion + decaprenyl-pyrophosphoryl-(N-acetylglucosamine)-N-acetylmuramyl-(pentapeptide) + UDP
undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl- D-alanine + UDP-N-acetyl-α-D-glucosamine → Hydrogen ion + undecaprenyl-diphospho-(N-acetylglucosamine)-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanine + UDP
undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl- D-alanyl-D-alanine + UDP-N-acetyl-α-D-glucosamine → Hydrogen ion + undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + UDP
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (n TMS)splash10-00di-9620000000-18841b4db9b69a91db36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-5543009000-8a176d160a1f074ab319View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-05cr-4796000000-6c09aa3a2dac66281973View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Kobayashi T, Sleeman JE, Coughtrie MW, Burchell B: Molecular and functional characterization of microsomal UDP-glucuronic acid uptake by members of the nucleotide sugar transporter (NST) family. Biochem J. 2006 Dec 1;400(2):281-9. [16965264 ]
  • Kim CH: Increased expression of N-acetylglucosaminyltransferase-V in human hepatoma cells by retinoic acid and 1alpha,25-dihydroxyvitamin D3. Int J Biochem Cell Biol. 2004 Nov;36(11):2307-19. [15313475 ]
  • Jamieson JC, Kaplan HA, Woloski BM, Hellman M, Ham K: Glycoprotein biosynthesis during the acute-phase response to inflammation. Can J Biochem Cell Biol. 1983 Sep;61(9):1041-8. [6627106 ]
  • Love DC, Hanover JA: The hexosamine signaling pathway: deciphering the "O-GlcNAc code". Sci STKE. 2005 Nov 29;2005(312):re13. [16317114 ]
  • Wells L, Vosseller K, Hart GW: A role for N-acetylglucosamine as a nutrient sensor and mediator of insulin resistance. Cell Mol Life Sci. 2003 Feb;60(2):222-8. [12678487 ]
Synthesis Reference: Takenouchi, Kenji; Ishige, Kazuya; Midorikawa, Yuichiro; Okuyama, Kiyoshi; Hamamoto, Tomoki; Noguchi, Toshitada. Process for producing uridine diphosphate-N-acetylglucosamine. PCT Int. Appl. (1999), 38 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS528-04-1
ChEBI57705
ChemSpider17600409
HMDBHMDB00290
IAF126033638
KEGGC00043
MetaboLightsMTBLC57705
PubChem16667373