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Human Metabolome Database Version 3.5

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Showing metabocard for Uridine diphosphate glucose (HMDB00286)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:14 -0700
HMDB ID HMDB00286
Secondary Accession Numbers None
Metabolite Identification
Common Name Uridine diphosphate glucose
Description Uridine 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C15H24N2O17P2
Average Molecular Weight 566.3018
Monoisotopic Molecular Weight 566.055020376
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 IUPAC 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 Number 133-89-1
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 Key HSCJRCZFDFQWRP-LPTOLDDLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Pyrimidine Nucleotides
Sub Class Pyrimidine 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 Parent Pyrimidine Nucleotide Sugars
Ontology
Status Detected 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
Application Not Available
Cellular locations
  • Endoplasmic reticulum
  • Golgi apparatus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 15 g/L ALOGPS
LogP -1.43 ALOGPS
LogP -5 ChemAxon
LogS -1.58 ALOGPS
pKa (strongest acidic) 1.73 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 14 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 291.54 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 106.46 ChemAxon
Polarizability 46.5 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Golgi apparatus
Biofluid Locations
  • Blood
Tissue Location
  • Skeletal Muscle
  • Liver
Pathways
Name SMPDB Link KEGG Link
Starch and Sucrose Metabolism SMP00058 map00500 Link_out
Lactose Synthesis SMP00444 Not Available
Galactose Metabolism SMP00043 map00052 Link_out
Nucleotide Sugars Metabolism SMP00010 map00520 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
155.0 +/- 113.0 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01861 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB005660
KNApSAcK ID C00001514 Link_out
Chemspider ID Not Available
KEGG Compound ID C00029 Link_out
BioCyc ID UDP-GLUCOSE Link_out
BiGG ID 33576 Link_out
Wikipedia Link Uridine diphosphate glucose Link_out
NuGOwiki Link HMDB00286 Link_out
Metagene Link HMDB00286 Link_out
METLIN ID 5278 Link_out
PubChem Compound 53477679 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Burma, 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. 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 Link_out
  2. 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 Link_out
  3. Hers HG: Mechanisms of blood glucose homeostasis. J Inherit Metab Dis. 1990;13(4):395-410. Pubmed: 2122108 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
Reactions:
  • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
Gene Name: ENPP1
Uniprot ID: P22413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 3
Reactions:
  • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
Gene Name: ENPP3
Uniprot ID: O14638 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sucrase-isomaltase, intestinal
Reactions:
  • Hydrolysis of sucrose and maltose by an alpha-D-glucosidase-type action [RN:R00801 R06087] ALL_REAC R00801 R06087(G) > R00802 R06088(G)
Gene Name: SI
Uniprot ID: P14410 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trehalase
Reactions:
  • alpha,alpha-trehalose + H2O = 2 D-glucose [RN:R00010 R06103]
Gene Name: TREH
Uniprot ID: O43280 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ceramide glucosyltransferase
Reactions:
  • UDP-glucose + an N-acylsphingosine = UDP + a D-glucosyl-N-acylsphingosine [RN:R01497 R06275]
Gene Name: UGCG
Uniprot ID: Q16739 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucose 4-epimerase
Reactions:
  • UDP-glucose = UDP-galactose [RN:R00291]
Gene Name: GALE
Uniprot ID: Q14376 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucose 6-dehydrogenase
Reactions:
  • UDP-glucose + 2 NAD+ + H2O = UDP-glucuronate + 2 NADH + 2 H+ [RN:R00286]
Gene Name: UGDH
Uniprot ID: O60701 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dolichyl-phosphate beta-glucosyltransferase
Reactions:
  • UDP-glucose + dolichyl phosphate = UDP + dolichyl beta-D-glucosyl phosphate [RN:R01005]
Gene Name: ALG5
Uniprot ID: Q9Y673 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UTP--glucose-1-phosphate uridylyltransferase
Reactions:
  • UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose [RN:R00289]
Gene Name: UGP2
Uniprot ID: Q16851 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen [starch] synthase, liver
Reactions:
  • UDP-glucose + [(1->4)-alpha-D-glucosyl]n = UDP + [(1->4)-alpha-D-glucosyl]n+1 [RN:R00292 R06051]
Gene Name: GYS2
Uniprot ID: P54840 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactose-1-phosphate uridylyltransferase
Reactions:
  • UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose [RN:R00955]
Gene Name: GALT
Uniprot ID: P07902 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogenin-1
Reactions:
  • UDP-alpha-D-glucose + glycogenin = UDP + alpha-D-glucosylglycogenin [RN:R03681]
Gene Name: GYG1
Uniprot ID: P46976 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen [starch] synthase, muscle
Reactions:
  • UDP-glucose + [(1->4)-alpha-D-glucosyl]n = UDP + [(1->4)-alpha-D-glucosyl]n+1 [RN:R00292 R06051]
Gene Name: GYS1
Uniprot ID: P13807 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogenin-2
Reactions:
  • UDP-alpha-D-glucose + glycogenin = UDP + alpha-D-glucosylglycogenin [RN:R03681]
Gene Name: GYG2
Uniprot ID: O15488 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine diphosphate glucose pyrophosphatase
Reactions:
  • UDP-sugar + H2O = UMP + alpha-D-aldose 1-phosphate [RN:R03986]
Gene Name: NUDT14
Uniprot ID: O95848 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA