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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:14 UTC
HMDB IDHMDB00286
Secondary Accession NumbersNone
Metabolite Identification
Common NameUridine diphosphate glucose
DescriptionUridine diphosphate glucose is a key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.
Structure
Thumb
Synonyms
  1. (UDP)glucose
  2. (UPD)-glucose
  3. UDP Glucose
  4. UDP-a-D-Glucose
  5. UDP-alpha-D-Glucose
  6. UDP-alpha-delta-Glucose
  7. UDP-D-Glucose
  8. UDP-delta-Glucose
  9. UDP-Glc
  10. UDP-Glucose
  11. UDPG
  12. UDPglucose
  13. Uridine 5'-diphosphate glucose
  14. Uridine 5'-diphospho-a-D-glucose
  15. Uridine 5'-diphospho-alpha-D-glucose
  16. Uridine 5'-diphospho-alpha-delta-glucose
  17. Uridine 5'-diphosphoglucose
  18. Uridine 5'-pyrophosphate a-D-glucopyranosyl ester
  19. Uridine 5'-pyrophosphate a-delta-glucopyranosyl ester
  20. Uridine diphosphate-glucose
  21. Uridine diphospho-D-glucose
  22. Uridine diphospho-delta-glucose
  23. Uridine diphosphoglucose
  24. Uridine pyrophosphate-glucose
Chemical FormulaC15H24N2O17P2
Average Molecular Weight566.3018
Monoisotopic Molecular Weight566.055020376
IUPAC Name[({[(2S,3R,4S,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional Name{[(2S,3R,4S,5S)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphinic acid
CAS Registry Number133-89-1
SMILES
OC[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)N2C=CC(=O)NC2=O)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14?/m0/s1
InChI KeyHSCJRCZFDFQWRP-LPTOLDDLSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPyrimidine Nucleotides
Sub ClassPyrimidine Nucleotide Sugars
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Pyrimidine Ribonucleoside Diphosphates
Substituents
  • 1,2 Diol
  • Disaccharide Phosphate
  • Glycosyl Compound
  • Hydropyrimidine
  • Mixed Pentose/Hexose Disaccharide
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxane
  • Oxolane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPyrimidine Nucleotide Sugars
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Galactose metabolism
  • Component of Glycosphingolipid metabolism
  • Component of N-Glycan biosynthesis
  • Component of Nucleotide sugars metabolism
  • Component of Starch and sucrose metabolism
ApplicationNot Available
Cellular locations
  • Endoplasmic reticulum
  • Golgi apparatus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.0ALOGPS
logP-1.4ALOGPS
logP-5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area291.54 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.46 m3·mol-1ChemAxon
Polarizability46.5 Å3ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Golgi apparatus
Biofluid Locations
  • Blood
Tissue Location
  • Liver
  • Skeletal Muscle
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043map00052
Lactose SynthesisSMP00444Not Available
Nucleotide Sugars MetabolismSMP00010map00520
Starch and Sucrose MetabolismSMP00058map00500
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified155.0 +/- 113.0 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01861
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB005660
KNApSAcK IDC00001514
Chemspider IDNot Available
KEGG Compound IDC00029
BioCyc IDUDP-GLUCOSE
BiGG ID33576
Wikipedia LinkUridine diphosphate glucose
NuGOwiki LinkHMDB00286
Metagene LinkHMDB00286
METLIN ID5278
PubChem Compound53477679
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceBurma, D. P.; Mortimer, D. C. Biosynthesis of uridine diphosphate glucose and sucrose in sugar-beet leaf. Archives of Biochemistry and Biophysics (1956), 62 16-28.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
  2. Tarantino G, Morelli L, Califano C: [Uridine diphosphate glucose (UDPG) in the treatment of hepatic disease from chronic alcohol abuse] Riv Eur Sci Med Farmacol. 1990 Apr;12(2):109-17. Pubmed: 2080308
  3. Schwartz AL, Rall TW: Hormonal regulation of glycogen metabolism in human fetal liver. II. Regulation of glycogen synthase activity. Diabetes. 1975 Dec;24(12):1113-22. Pubmed: 811498
  4. Hers HG: Mechanisms of blood glucose homeostasis. J Inherit Metab Dis. 1990;13(4):395-410. Pubmed: 2122108
  5. Raila J, Wirth K, Chen F, Buscher U, Dudenhausen JW, Schweigert FJ: Excretion of vitamin A in urine of women during normal pregnancy and pregnancy complications. Ann Nutr Metab. 2004 Sep-Oct;48(5):357-64. Epub 2004 Nov 9. Pubmed: 15542927
  6. Ng WG, Xu YK, Kaufman FR, Donnell GN: Deficit of uridine diphosphate galactose in galactosaemia. J Inherit Metab Dis. 1989;12(3):257-66. Pubmed: 2515367
  7. Marschall HU, Matern H, Wietholtz H, Egestad B, Matern S, Sjovall J: Bile acid N-acetylglucosaminidation. In vivo and in vitro evidence for a selective conjugation reaction of 7 beta-hydroxylated bile acids in humans. J Clin Invest. 1992 Jun;89(6):1981-7. Pubmed: 1602004
  8. Haugen HF, Skrede S: Nucleotide pyrophosphatase and phosphodiesterase I. Demonstration of activity in normal serum, and an increase in cholestatic liver disease. Scand J Gastroenterol. 1976;11(2):121-7. Pubmed: 4880
  9. Reynolds TH 4th, Pak Y, Harris TE, Manchester J, Barrett EJ, Lawrence JC Jr: Effects of insulin and transgenic overexpression of UDP-glucose pyrophosphorylase on UDP-glucose and glycogen accumulation in skeletal muscle fibers. J Biol Chem. 2005 Feb 18;280(7):5510-5. Epub 2004 Dec 13. Pubmed: 15596435
  10. Nielsen JN, Richter EA: Regulation of glycogen synthase in skeletal muscle during exercise. Acta Physiol Scand. 2003 Aug;178(4):309-19. Pubmed: 12864735

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
Reactions
Uridine diphosphate glucose + Water → Uridine 5'-monophosphate + Glucose 1-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
ENPP3
Uniprot ID:
O14638
Molecular weight:
100123.54
Reactions
Uridine diphosphate glucose + Water → Uridine 5'-monophosphate + Glucose 1-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name:
SI
Uniprot ID:
P14410
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
Intestinal trehalase is probably involved in the hydrolysis of ingested trehalose.
Gene Name:
TREH
Uniprot ID:
O43280
Molecular weight:
66567.26
General function:
Involved in oxidoreductase activity
Specific function:
Forms hydroxylysine residues in -Xaa-Lys-Gly- sequences in collagens. These hydroxylysines serve as sites of attachment for carbohydrate units and are essential for the stability of the intermolecular collagen cross-links.
Gene Name:
PLOD3
Uniprot ID:
O60568
Molecular weight:
84784.505
Reactions
Uridine diphosphate glucose + 5-(D-Galactosyloxy)-L-lysine-procollagen → Uridine 5'-diphosphate + 1,2-D-Glucosyl-5-D-(galactosyloxy)-L-lysine-procollagendetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the first glycosylation step in glycosphingolipid biosynthesis, the transfer of glucose to ceramide. May also serve as a "flippase".
Gene Name:
UGCG
Uniprot ID:
Q16739
Molecular weight:
44853.255
Reactions
Uridine diphosphate glucose + N-acylsphingosine → Uridine 5'-diphosphate + D-glucosyl-N-acylsphingosinedetails
Uridine diphosphate glucose + N-Acylsphingosine → Uridine 5'-diphosphate + beta-D-Glucosyl-(1<->1)-ceramidedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes two distinct but analogous reactions: the epimerization of UDP-glucose to UDP-galactose and the epimerization of UDP-N-acetylglucosamine to UDP-N-acetylgalactosamine.
Gene Name:
GALE
Uniprot ID:
Q14376
Molecular weight:
38281.435
Reactions
Uridine diphosphate glucose → Uridine diphosphategalactosedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in oxidoreductase activity
Specific function:
Involved in the biosynthesis of glycosaminoglycans; hyaluronan, chondroitin sulfate, and heparan sulfate.
Gene Name:
UGDH
Uniprot ID:
O60701
Molecular weight:
47602.08
Reactions
Uridine diphosphate glucose + NAD + Water → Uridine diphosphate glucuronic acid + NADHdetails
Uridine diphosphate glucose + Water + NAD → Uridine diphosphate glucuronic acid + NADH + Hydrogen Iondetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Not Available
Gene Name:
ALG5
Uniprot ID:
Q9Y673
Molecular weight:
33524.965
Reactions
Uridine diphosphate glucose + Dolichol-20 → Uridine 5'-diphosphate + Dolichyl b-D-glucosyl phosphatedetails
General function:
Involved in nucleotidyltransferase activity
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways.
Gene Name:
UGP2
Uniprot ID:
Q16851
Molecular weight:
55676.36
Reactions
Uridine triphosphate + Glucose 1-phosphate → Pyrophosphate + Uridine diphosphate glucosedetails
General function:
Involved in glycogen (starch) synthase activity
Specific function:
Transfers the glycosyl residue from UDP-Glc to the non-reducing end of alpha-1,4-glucan.
Gene Name:
GYS2
Uniprot ID:
P54840
Molecular weight:
80988.42
Reactions
Uridine diphosphate glucose + Amylose → Uridine 5'-diphosphate + Amylosedetails
General function:
Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
Specific function:
Not Available
Gene Name:
GALT
Uniprot ID:
P07902
Molecular weight:
43362.83
Reactions
Uridine diphosphate glucose + Galactose 1-phosphate → Glucose 1-phosphate + Uridine diphosphategalactosedetails
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Self-glucosylates, via an inter-subunit mechanism, to form an oligosaccharide primer that serves as substrate for glycogen synthase.
Gene Name:
GYG1
Uniprot ID:
P46976
Molecular weight:
37478.2
Reactions
Uridine diphosphate glucose + glycogenin → Uridine 5'-diphosphate + alpha-D-glucosylglycogenindetails
General function:
Involved in glycogen (starch) synthase activity
Specific function:
Transfers the glycosyl residue from UDP-Glc to the non-reducing end of alpha-1,4-glucan.
Gene Name:
GYS1
Uniprot ID:
P13807
Molecular weight:
76482.48
Reactions
Uridine diphosphate glucose + Amylose → Uridine 5'-diphosphate + Amylosedetails
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Self-glucosylates, via an inter-subunit mechanism, to form an oligosaccharide primer that serves as substrate for glycogen synthase.
Gene Name:
GYG2
Uniprot ID:
O15488
Molecular weight:
51998.955
Reactions
Uridine diphosphate glucose + glycogenin → Uridine 5'-diphosphate + alpha-D-glucosylglycogenindetails
General function:
Involved in hydrolase activity, acting on acid anhydrides, in phosphorus-containing anhydrides
Specific function:
Hydrolyzes UDP-glucose to glucose 1-phosphate and UMP and ADP-ribose to ribose 5-phosphate and AMP. The physiological substrate is probably UDP-glucose. Poor activity on other substrates such as ADP-glucose, CDP-glucose, GDP-glucose and GDP-mannose.
Gene Name:
NUDT14
Uniprot ID:
O95848
Molecular weight:
24118.085