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UDP-D-glucose (YMDB00415)

Identification
YMDB IDYMDB00415
NameUDP-D-glucose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUridine diphosphate glucose (UDP-glucose) is a nucleotide sugar. UDP-glucose consists of the pyrophosphate group, the pentose sugar ribose, glucose, and the nucleobase uracil. It is involved in glycosyltransferase reactions. It is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid. UDP-glucose can also be used as a precursor of sucrose lipopolysaccharides, and glycosphingolipids. [Wikipedia]
Structure
Thumb
MOLSDFPDBSMILESInChI
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'-(trihydrogen diphosphate), mono-alpha-d-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphate), P'-alpha-D-glucopyranosyl ester
  • 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 diphosphate-glucose
  • Uridine diphospho-D-glucose
  • Uridine diphospho-delta-glucose
  • Uridine diphosphoglucose
  • Uridine pyrophosphate-glucose
  • uridinediphosphoglucose
  • Uridine 5'-(trihydrogen diphosphate), mono-a-D-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphate), mono-α-D-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphoric acid), mono-a-D-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphoric acid), mono-α-D-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphate), p'-a-D-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphate), p'-α-D-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-a-D-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-alpha-D-glucopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-α-D-glucopyranosyl ester
  • Uridine diphosphoric acid glucose
CAS number133-89-1
WeightAverage: 566.3018
Monoisotopic: 566.055020376
InChI KeyHSCJRCZFDFQWRP-RDKQLNKOSA-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?/m1/s1
IUPAC Name[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional IUPAC Nameudp-glc
Chemical FormulaC15H24N2O17P2
SMILESOC[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
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
Polarizability45.34 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 ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
150 ± 0 µM Minimal medium supplemented with ammonia salts and glucoseaerobic;resting cellsBaker's yeastPMID: 4578278
300 ± 0 µM Minimal medium supplemented with ammonia salts and glucoseaerobic;growing cellsBaker's yeastPMID: 4578278
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_32) - 70eV, PositiveNot AvailableJSpectraViewer
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
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
  • Roemer, T., Delaney, S., Bussey, H. (1993). "SKN1 and KRE6 define a pair of functional homologs encoding putative membrane proteins involved in beta-glucan synthesis." Mol Cell Biol 13:4039-4048.8321211
  • Inoue, S. B., Takewaki, N., Takasuka, T., Mio, T., Adachi, M., Fujii, Y., Miyamoto, C., Arisawa, M., Furuichi, Y., Watanabe, T. (1995). "Characterization and gene cloning of 1,3-beta-D-glucan synthase from Saccharomyces cerevisiae." Eur J Biochem 231:845-854.7649185
  • De Virgilio, C., Burckert, N., Bell, W., Jeno, P., Boller, T., Wiemken, A. (1993). "Disruption of TPS2, the gene encoding the 100-kDa subunit of the trehalose-6-phosphate synthase/phosphatase complex in Saccharomyces cerevisiae, causes accumulation of trehalose-6-phosphate and loss of trehalose-6-phosphate phosphatase activity." Eur J Biochem 212:315-323.8444170
  • Mu, J., Cheng, C., Roach, P. J. (1996). "Initiation of glycogen synthesis in yeast. Requirement of multiple tyrosine residues for function of the self-glucosylating Glg proteins in vivo." J Biol Chem 271:26554-26560.8900126
  • Warnecke, D., Erdmann, R., Fahl, A., Hube, B., Muller, F., Zank, T., Zahringer, U., Heinz, E. (1999). "Cloning and functional expression of UGT genes encoding sterol glucosyltransferases from Saccharomyces cerevisiae, Candida albicans, Pichia pastoris, and Dictyostelium discoideum." J Biol Chem 274:13048-13059.10224056
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18066
HMDB IDHMDB00286
Pubchem Compound ID8629
Kegg IDC00029
ChemSpider ID23105735
FOODB IDNot Available
WikipediaUridine_diphosphate_glucose
BioCyc IDUDP-GLUCOSE

Enzymes

Protein Details
1. Galactose-1-phosphate uridylyltransferase
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.
Protein Details
2. Ectonucleotide pyrophosphatase/phosphodiesterase 1
General function:
Involved in catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP2 and PHO5
Gene Name:
NPP1
Uniprot ID:
P25353
Molecular weight:
84733.20313
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
Protein Details
3. Ectonucleotide pyrophosphatase/phosphodiesterase 2
General function:
Involved in catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and PHO5
Gene Name:
NPP2
Uniprot ID:
P39997
Molecular weight:
57354.10156
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
Protein Details
4. Bifunctional protein GAL10
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.
Protein Details
5. 1,3-beta-glucan synthase component FKS1
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).
Protein Details
6. Probable UTP--glucose-1-phosphate uridylyltransferase
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.
Protein Details
7. 1,3-beta-glucan synthase component FKS3
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).
Protein Details
8. 1,3-beta-glucan synthase component GSC2
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).
Protein Details
9. UTP--glucose-1-phosphate uridylyltransferase
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.
Protein Details
10. Alpha,alpha-trehalose-phosphate synthase [UDP-forming] 56 kDa subunit
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.
Protein Details
11. Sterol 3-beta-glucosyltransferase
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.
Protein Details
12. Beta-glucan synthesis-associated protein KRE6
General function:
Carbohydrate transport and metabolism
Specific function:
Involved in the synthesis of (1->6)- and (1->3)-beta-D- glucan polymers of the yeast cell wall in vivo. It is required for full activity of beta-glucan synthase in vitro. May be involved in the maturation and transport of cell wall proteins (CWP) to the cell wall. May act as a transglucosidase and contribute to the construction of a protein-bound glucan-structure that acts as an acceptor site for the addition of (1->6)-beta-D-glucan at the cell surface
Gene Name:
KRE6
Uniprot ID:
P32486
Molecular weight:
80122.10156
Reactions
Protein Details
13. Trehalose synthase complex regulatory subunit TPS3
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
Protein Details
14. Glycogen [starch] synthase isoform 2
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).
Protein Details
15. Glycogen [starch] synthase isoform 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).
Protein Details
16. Beta-glucan synthesis-associated protein SKN1
General function:
Carbohydrate transport and metabolism
Specific function:
Required for synthesis of the major beta-glucans of the yeast cell wall
Gene Name:
SKN1
Uniprot ID:
P33336
Molecular weight:
86240.39844
Reactions