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Identification
YMDB IDYMDB00692
NameUDP-D-galactose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUDP-D-galactose, also known as UDP galactose or udpgal, 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. UDP-D-galactose is an extremely weak basic (essentially neutral) compound (based on its pKa). UDP-D-galactose may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • GALACTOSE-URIDINE-5'-DIPHOSPHATE
  • GDU
  • Udp galactose
  • UDP-a-D-Galactose
  • Udp-alpha-d-galactose
  • UDP-alpha-delta-Galactose
  • udp-d-galactopyranose
  • UDP-D-galactose
  • Udp-delta-galactopyranose
  • UDP-delta-galactose
  • UDP-Gal
  • UDP-galactopyranose
  • UDP-galactose
  • Udpgal
  • UDPgalactose
  • UPG
  • Uridine 5'-(alpha-D-galactopyranosyl pyrophosphate)
  • Uridine 5'-(alpha-delta-galactopyranosyl pyrophosphate)
  • Uridine 5'-(trihydrogen diphosphate), P'-alpha-D-galactopyranosyl ester
  • uridine 5'-[3-(D-galactopyranosyl) dihydrogen diphosphate]
  • Uridine 5'-diphosphate galactose
  • Uridine 5'-diphosphogalactose
  • Uridine 5'-pyrophosphate a-D-galactopyranosyl ester
  • Uridine 5'-pyrophosphate a-D-galactosyl ester
  • Uridine 5'-pyrophosphate a-delta-galactopyranosyl ester
  • Uridine 5'-pyrophosphate a-delta-galactosyl ester
  • Uridine 5'-pyrophosphate alpha-D-galactosyl ester
  • Uridine 5'-pyrophosphate alpha-delta-galactosyl ester
  • Uridine 5'-pyrophosphate D-galactosyl ester
  • Uridine diphosphate galactose
  • Uridine diphosphate-D-galactose
  • Uridine diphosphate-delta-galactose
  • Uridine diphosphate-galactose
  • Uridine diphosphogalactose
  • Uridine pyrophosphate a-D-galactopyranosyl ester
  • Uridine pyrophosphate a-delta-galactopyranosyl ester
  • Uridine pyrophosphate alpha-d-galactopyranosyl ester
  • Uridine pyrophosphate alpha-delta-galactopyranosyl ester
  • Uridine pyrophosphogalactose
  • Uridinediphosphate galactose
  • Uridinediphosphogalactose
  • Uridine 5'-(trihydrogen diphosphate), p'-a-D-galactopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphate), p'-α-D-galactopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-a-D-galactopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-alpha-D-galactopyranosyl ester
  • Uridine 5'-(trihydrogen diphosphoric acid), p'-α-D-galactopyranosyl ester
  • Uridine diphosphoric acid galactose
  • Uridine diphosphoric acid-galactose
CAS number2956-16-3
WeightAverage: 566.3018
Monoisotopic: 566.055020376
InChI KeyHSCJRCZFDFQWRP-LNYDKVEPSA-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,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional IUPAC Nameuridine diphosphate-galactose
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
Polarizability45.44 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Golgi
  • 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
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Galactose metabolismec00052 Map00052
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
Uridine diphosphate glucoseUDP-D-galactose
KEGG Reactions
Uridine triphosphate + Galactose 1-phosphate + hydronPyrophosphate + UDP-D-galactose
Uridine diphosphate glucoseUDP-D-galactose
Galactose 1-phosphate + Uridine diphosphate glucoseUDP-D-galactose + Glucose 1-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
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:
  • 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
  • Barber, C., Rosti, J., Rawat, A., Findlay, K., Roberts, K., Seifert, G. J. (2006). "Distinct properties of the five UDP-D-glucose/UDP-D-galactose 4-epimerase isoforms of Arabidopsis thaliana." J Biol Chem 281:17276-17285.16644739
  • Oka, T., Jigami, Y. (2006). "Reconstruction of de novo pathway for synthesis of UDP-glucuronic acid and UDP-xylose from intrinsic UDP-glucose in Saccharomyces cerevisiae." FEBS J 273:2645-2657.16817893
Synthesis Reference:Takeda, Satoshi; Noguchi, Toshitada. Enzymic manufacture of 5'-uridine diphosphate galactose (UDP-Gal) from UMP. Jpn. Kokai Tokkyo Koho (2001), 9 pp.
External Links:
ResourceLink
CHEBI ID18307
HMDB IDHMDB00302
Pubchem Compound ID46936243
Kegg IDC00052
ChemSpider ID23105735
FOODB IDNot Available
WikipediaUridine_diphosphate_galactose
BioCyc IDUDP-GLACTOSE

Enzymes

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 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.

Transporters

General function:
Involved in transmembrane transport
Specific function:
May be involved in specific transport of UDP-Gal from the cytosol to the Golgi lumen. Involved in the maintenance of optimal conditions for the folding of secretory pathway proteins in the endoplasmic reticulum. Overexpression confers resistance to the immunosuppressive drug, leflunomide
Gene Name:
HUT1
Uniprot ID:
Q12520
Molecular weight:
38075.19922