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Identification
YMDB IDYMDB00212
NameUridine diphosphate glucose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUridine diphosphate glucose, also known as udpglucose or UDP-alpha-D-glucose, 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. Uridine diphosphate glucose is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphate glucose exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (UDP)glucose
  • (UPD)-glucose
  • UDP glucose
  • UDP-a-D-Glucose
  • UDP-alpha-D-Glucose
  • UDP-alpha-delta-Glucose
  • UDP-D-glucose
  • UDP-delta-glucose
  • UDP-Glc
  • UDP-Glucose
  • UDPG
  • UDPglucose
  • Uridine 5'-diphosphate glucose
  • Uridine 5'-diphospho-a-D-glucose
  • Uridine 5'-diphospho-alpha-D-glucose
  • Uridine 5'-diphospho-alpha-delta-glucose
  • Uridine 5'-diphosphoglucose
  • Uridine 5'-pyrophosphate a-D-glucopyranosyl ester
  • Uridine 5'-pyrophosphate a-delta-glucopyranosyl ester
  • Uridine diphosphate-glucose
  • Uridine diphospho-D-glucose
  • Uridine diphospho-delta-glucose
  • Uridine diphosphoglucose
  • Uridine pyrophosphate-glucose
  • GLUCOSE-uridine-C1,5'-diphosphATE
  • URIDINE-5'-diphosphATE-glucose
  • GLUCOSE-uridine-C1,5'-diphosphoric acid
  • URIDINE-5'-diphosphoric acid-glucose
  • UDP-Α-D-glucose
  • Uridine diphosphoric acid glucose
  • Diphosphate glucose, uridine
  • Diphosphoglucose, uridine
  • Glucose, UDP
  • Glucose, uridine diphosphate
  • Uridine 5'-(alpha-D-glucopyranosyl pyrophosphate)
  • Uridine 5'-(α-D-glucopyranosyl pyrophosphate)
  • Uridine 5'-diphospho-α-D-glucose
  • Uridine 5’-(α-D-glucopyranosyl pyrophosphate)
  • Uridine 5’-diphosphate glucose
  • Uridine 5’-diphospho-α-D-glucose
  • Uridine 5’-diphosphoglucose
  • Uridine diphosphate glucose
CAS number133-89-1
WeightAverage: 566.3018
Monoisotopic: 566.055020376
InChI KeyHSCJRCZFDFQWRP-LPTOLDDLSA-N
InChIInChI=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
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
Chemical FormulaC15H24N2O17P2
SMILES[H]OC([H])([H])[C@]1([H])OC([H])(OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@]2([H])O[C@]([H])(N3C([H])=C([H])C(=O)N([H])C3=O)[C@@]([H])(O[H])[C@@]2([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]
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
  • 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
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Urea
  • Secondary alcohol
  • Lactam
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Leloir PathwayPW002397 ThumbThumb?image type=greyscaleThumb?image type=simple
N-Glycan biosynthesisPW002501 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Galactose metabolismec00052 Map00052
Glycerolipid metabolismec00561 Map00561
N-Glycan biosynthesisec00510 Map00510
Pentose and glucuronate interconversionsec00040 Map00040
SMPDB Reactions
UDP-D-galactoseUridine diphosphate glucose
Galactose 1-phosphate + Uridine diphosphate glucoseGlucose 1-phosphate + UDP-D-galactose
UDP-D-galactose + Glucose 1-phosphateUridine diphosphate glucose + Galactose 1-phosphate
Glucose 1-phosphate + Uridine triphosphate + hydronUridine diphosphate glucose + Uridine 5'-diphosphate
Uridine diphosphate glucoseUDP-D-galactose
KEGG Reactions
Uridine diphosphate glucoseUDP-D-galactose
Galactose 1-phosphate + Uridine diphosphate glucoseUDP-D-galactose + Glucose 1-phosphate
Uridine triphosphate + Glucose 1-phosphate + hydronPyrophosphate + Uridine diphosphate glucose
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-3933570000-89f658b2d26ff158d84cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-4942706000-3a83736296429f83adeeJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0000090000-1692ab5f5dad1cf7e436JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-015a-0439510000-69e7cd4c2c365a24706bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0109-5753970000-03f34041208ba93ef87aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-4b81825405869909992eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-6fd09254750e77963110JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-03a2a98eb0aa84737530JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4901260000-8396a090c14de7f2d708JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-8907020000-94410556a0288cb8167bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5901000000-10132c85ad33464d4eefJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • DOUGLAS, H. C., HAWTHORNE, D. C. (1964). "ENZYMATIC EXPRESSION AND GENETIC LINKAGE OF GENES CONTROLLING GALACTOSE UTILIZATION IN SACCHAROMYCES." Genetics 49:837-844.14158615
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.
External Links:
ResourceLink
CHEBI ID18066
HMDB IDHMDB00286
Pubchem Compound ID439156
Kegg IDC00029
ChemSpider ID23105735
FOODB IDFDB005660
WikipediaUridine diphosphate glucose
BioCyc IDUDP-GLUCOSE

Enzymes

General function:
Cell wall/membrane/envelope biogenesis
Specific function:
UDP-glucose + dolichyl phosphate = UDP + dolichyl beta-D-glucosyl phosphate
Gene Name:
ALG5
Uniprot ID:
P40350
Molecular weight:
38346.39844
Reactions
UDP-glucose + dolichyl phosphate → UDP + dolichyl beta-D-glucosyl phosphate.
General function:
Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
Specific function:
UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose
Gene Name:
GAL7
Uniprot ID:
P08431
Molecular weight:
42384.69922
Reactions
UDP-glucose + alpha-D-galactose 1-phosphate → alpha-D-glucose 1-phosphate + UDP-galactose.
General function:
Involved in catalytic activity
Specific function:
Phosphatase catalytic subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process
Gene Name:
TPS2
Uniprot ID:
P31688
Molecular weight:
102976.0
Reactions
Trehalose 6-phosphate + H(2)O → trehalose + phosphate.
General function:
Involved in isomerase activity
Specific function:
Mutarotase converts alpha-aldose to the beta-anomer. It is active on D-glucose, L-arabinose, D-xylose, D-galactose, maltose and lactose
Gene Name:
GAL10
Uniprot ID:
P04397
Molecular weight:
78194.70313
Reactions
UDP-glucose → UDP-galactose.
Alpha-D-glucose → beta-D-glucose.
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Self-glucosylating initiator of glycogen synthesis. Catalyzes the formation of a short alpha (1,4)-glucosyl chain covalently attached via a glucose 1-O-tyrosyl linkage to internal tyrosine residues. These chains act as primers for the elongation reaction catalyzed by glycogen synthase. Capable of transferring glucosyl residues to unbound acceptors such as free oligoglucans or oligoglucan derivatives
Gene Name:
GLG2
Uniprot ID:
P47011
Molecular weight:
44545.60156
Reactions
UDP-alpha-D-glucose + glycogenin → UDP + alpha-D-glucosylglycogenin.
General function:
Involved in 1,3-beta-D-glucan synthase activity
Specific function:
Alternate catalytic subunit of the 1,3-beta-glucan synthase (GS). Synthesizes 1,3-beta-glucan, a major structural component of the yeast cell wall. Involved in cell wall synthesis, maintenance and cell wall remodeling
Gene Name:
FKS1
Uniprot ID:
P38631
Molecular weight:
214849.0
Reactions
UDP-glucose + ((1->3)-beta-D-glucosyl)(n) → UDP + ((1->3)-beta-D-glucosyl)(n+1).
General function:
Involved in nucleotidyltransferase activity
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways
Gene Name:
Not Available
Uniprot ID:
P38709
Molecular weight:
55999.80078
Reactions
UTP + alpha-D-glucose 1-phosphate → diphosphate + UDP-glucose.
General function:
Involved in 1,3-beta-D-glucan synthase activity
Specific function:
Required for spore wall assembly
Gene Name:
FKS3
Uniprot ID:
Q04952
Molecular weight:
207481.0
Reactions
UDP-glucose + ((1->3)-beta-D-glucosyl)(n) → UDP + ((1->3)-beta-D-glucosyl)(n+1).
General function:
Involved in 1,3-beta-D-glucan synthase activity
Specific function:
Alternate catalytic subunit of the 1,3-beta-glucan synthase (GS). Synthesizes 1,3-beta-glucan, a major structural component of the yeast cell wall. Required for spore wall assembly. Negative regulation of activity by SMK1 is important for spore wall deposition. Activity is positively regulated by RHO1
Gene Name:
GSC2
Uniprot ID:
P40989
Molecular weight:
216988.0
Reactions
UDP-glucose + ((1->3)-beta-D-glucosyl)(n) → UDP + ((1->3)-beta-D-glucosyl)(n+1).
General function:
Involved in nucleotidyltransferase activity
Specific function:
Plays a central role as a glucosyl donor in cellular metabolic pathways
Gene Name:
UGP1
Uniprot ID:
P32861
Molecular weight:
55987.39844
Reactions
UTP + alpha-D-glucose 1-phosphate → diphosphate + UDP-glucose.
General function:
Involved in catalytic activity
Specific function:
Synthase catalytic subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process. Can function independently of the complex
Gene Name:
TPS1
Uniprot ID:
Q00764
Molecular weight:
56147.5
Reactions
UDP-glucose + D-glucose 6-phosphate → UDP + alpha,alpha-trehalose 6-phosphate.
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
May be involved in decane metabolism and autophagy. Involved in the biosynthesis of sterol glucoside
Gene Name:
ATG26
Uniprot ID:
Q06321
Molecular weight:
136053.0
Reactions
UDP-glucose + a sterol → UDP + a sterol 3-beta-D-glucoside.
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Self-glucosylating initiator of glycogen synthesis. Catalyzes the formation of a short alpha (1,4)-glucosyl chain covalently attached via a glucose 1-O-tyrosyl linkage to internal tyrosine residues. These chains act as primers for the elongation reaction catalyzed by glycogen synthase. Capable of transferring glucosyl residues to unbound acceptors such as free oligoglucans or oligoglucan derivatives
Gene Name:
GLG1
Uniprot ID:
P36143
Molecular weight:
69723.39844
Reactions
UDP-alpha-D-glucose + glycogenin → UDP + alpha-D-glucosylglycogenin.
General function:
Involved in catalytic activity
Specific function:
Regulatory subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process. May stabilize the trehalose synthase complex
Gene Name:
TPS3
Uniprot ID:
P38426
Molecular weight:
118834.0
Reactions
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. Is believed to regulate the synthesis of glycogen
Gene Name:
GSY2
Uniprot ID:
P27472
Molecular weight:
80078.20313
Reactions
UDP-glucose ((1->4)-alpha-D-glucosyl)(n) → UDP + ((1->4)-alpha-D-glucosyl)(n+1).
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. Is believed to regulate the synthesis of glycogen
Gene Name:
GSY1
Uniprot ID:
P23337
Molecular weight:
80509.60156
Reactions
UDP-glucose ((1->4)-alpha-D-glucosyl)(n) → UDP + ((1->4)-alpha-D-glucosyl)(n+1).