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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:15:51 UTC
HMDB IDHMDB0000286
Secondary Accession Numbers
  • HMDB00286
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
ValueSource
(UDP)GlucoseHMDB
(UPD)-glucoseHMDB
UDP GlucoseHMDB
UDP-a-D-GlucoseHMDB
UDP-alpha-D-GlucoseHMDB
UDP-alpha-delta-GlucoseHMDB
UDP-D-GlucoseHMDB
UDP-delta-GlucoseHMDB
UDP-GLCHMDB
UDP-GlucoseHMDB
UDPGHMDB
UDPglucoseHMDB
Uridine 5'-diphosphate glucoseHMDB
Uridine 5'-diphospho-a-D-glucoseHMDB
Uridine 5'-diphospho-alpha-D-glucoseHMDB
Uridine 5'-diphospho-alpha-delta-glucoseHMDB
Uridine 5'-diphosphoglucoseHMDB
Uridine 5'-pyrophosphate a-D-glucopyranosyl esterHMDB
Uridine 5'-pyrophosphate a-delta-glucopyranosyl esterHMDB
Uridine diphosphate-glucoseHMDB
Uridine diphospho-D-glucoseHMDB
Uridine diphospho-delta-glucoseHMDB
Uridine diphosphoglucoseHMDB
Uridine pyrophosphate-glucoseHMDB
Glucose, UDPMeSH
Diphosphate glucose, uridineMeSH
Diphosphoglucose, uridineMeSH
Glucose, uridine diphosphateMeSH
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
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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Oxane
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Hydropyrimidine
  • Heteroaromatic compound
  • Oxolane
  • Vinylogous amide
  • Urea
  • Secondary alcohol
  • Lactam
  • Organoheterocyclic compound
  • Polyol
  • Azacycle
  • Oxacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.46 m³·mol⁻¹ChemAxon
Polarizability46.5 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-3933570000-89f658b2d26ff158d84cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7542419000-5b7cd6dd9206b30f1209View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0000090000-1692ab5f5dad1cf7e436View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-015a-0439510000-69e7cd4c2c365a24706bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0109-5753970000-03f34041208ba93ef87aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-4b81825405869909992eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-6fd09254750e77963110View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-03a2a98eb0aa84737530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4901260000-8396a090c14de7f2d708View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-8907020000-94410556a0288cb8167bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5901000000-10132c85ad33464d4eefView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Golgi apparatus
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Liver
  • Skeletal Muscle
Pathways
NameSMPDB/PathwhizKEGG
Congenital disorder of glycosylation CDG-IIdPw000555Pw000555 greyscalePw000555 simpleNot Available
Fabry diseasePw000501Pw000501 greyscalePw000501 simpleNot Available
GLUT-1 deficiency syndromePw000556Pw000556 greyscalePw000556 simpleNot Available
Galactose MetabolismPw000159Pw000159 greyscalePw000159 simpleMap00052
GalactosemiaPw000200Pw000200 greyscalePw000200 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified155.0 +/- 113.0 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.993 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Femaleankylosing spondylitis details
FecesDetected but not Quantified Adult (>18 years old)Femalerheumatoid arthritis details
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
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