Record Information
Version2.0
Creation Date2012-05-31 10:26:07 -0600
Update Date2015-09-17 15:41:03 -0600
Secondary Accession Numbers
  • ECMDB00302
Identification
Name:Uridine diphosphategalactose
Description:Uridine diphosphategalactose (UDPgal) is a nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. UDPgal is a pivotal compound in the metabolism of galactose. UDPgal is a product of the galactose-L-phosphate uridyl transferase (EC 2.7.7.10) reaction but may also be made from Glucose-L-P, involving uridine diphosphate galactose-4-epimerase (EC 5.1.3.2). UDPgal is the necessary galactosyl donor of galactose in the metabolism to incorporate it into complex oligosaccharides, glycoproteins and glycolipids (galactosides). (PMID: 2122114, 7671968)
Structure
Thumb
Synonyms:
  • GDU
  • UDP Galactose
  • UDP-a-D-Galactose
  • UDP-a-delta-Galactose
  • UDP-a-δ-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
  • UDP-α-D-Galactose
  • UDP-α-δ-Galactose
  • UDP-δ-Galactopyranose
  • UDP-δ-Galactose
  • Udpgal
  • UDPgalactose
  • UPG
  • Uridine 5'-(a-D-galactopyranosyl pyrophosphate)
  • Uridine 5'-(a-D-galactopyranosyl pyrophosphoric acid)
  • Uridine 5'-(a-delta-galactopyranosyl pyrophosphate)
  • Uridine 5'-(a-delta-galactopyranosyl pyrophosphoric acid)
  • Uridine 5'-(a-δ-galactopyranosyl pyrophosphate)
  • Uridine 5'-(a-δ-galactopyranosyl pyrophosphoric acid)
  • Uridine 5'-(alpha-D-galactopyranosyl pyrophosphate)
  • Uridine 5'-(alpha-D-galactopyranosyl pyrophosphoric acid)
  • Uridine 5'-(alpha-delta-galactopyranosyl pyrophosphate)
  • Uridine 5'-(alpha-delta-galactopyranosyl pyrophosphoric acid)
  • Uridine 5'-(α-D-galactopyranosyl pyrophosphate)
  • Uridine 5'-(α-D-galactopyranosyl pyrophosphoric acid)
  • Uridine 5'-(α-δ-galactopyranosyl pyrophosphate)
  • Uridine 5'-(α-δ-galactopyranosyl pyrophosphoric acid)
  • Uridine 5'-diphosphate galactose
  • Uridine 5'-diphosphogalactose
  • Uridine 5'-diphosphoric acid galactose
  • 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 a-δ-galactopyranosyl ester
  • Uridine 5'-pyrophosphate a-δ-galactosyl ester
  • Uridine 5'-pyrophosphate alpha-D-galactosyl ester
  • Uridine 5'-pyrophosphate alpha-delta-galactosyl ester
  • Uridine 5'-pyrophosphate D-galactosyl ester
  • Uridine 5'-pyrophosphate α-D-galactosyl ester
  • Uridine 5'-pyrophosphate α-δ-galactosyl ester
  • Uridine 5'-pyrophosphoric acid a-D-galactopyranosyl ester
  • Uridine 5'-pyrophosphoric acid a-D-galactosyl ester
  • Uridine 5'-pyrophosphoric acid a-delta-galactopyranosyl ester
  • Uridine 5'-pyrophosphoric acid a-delta-galactosyl ester
  • Uridine 5'-pyrophosphoric acid a-δ-galactopyranosyl ester
  • Uridine 5'-pyrophosphoric acid a-δ-galactosyl ester
  • Uridine 5'-pyrophosphoric acid alpha-D-galactosyl ester
  • Uridine 5'-pyrophosphoric acid alpha-delta-galactosyl ester
  • Uridine 5'-pyrophosphoric acid D-galactosyl ester
  • Uridine 5'-pyrophosphoric acid α-D-galactosyl ester
  • Uridine 5'-pyrophosphoric acid α-δ-galactosyl ester
  • Uridine 5'-[3-(D-galactopyranosyl) dihydrogen diphosphate]
  • Uridine 5'-[3-(D-galactopyranosyl) dihydrogen diphosphoric acid]
  • Uridine diphosphate galactose
  • Uridine diphosphate-D-galactose
  • Uridine diphosphate-delta-galactose
  • Uridine diphosphate-galactose
  • Uridine diphosphate-δ-galactose
  • Uridine diphosphogalactose
  • Uridine diphosphoric acid galactose
  • Uridine diphosphoric acid-D-galactose
  • Uridine diphosphoric acid-delta-galactose
  • Uridine diphosphoric acid-galactose
  • Uridine diphosphoric acid-δ-galactose
  • Uridine pyrophosphate a-D-galactopyranosyl ester
  • Uridine pyrophosphate a-delta-galactopyranosyl ester
  • Uridine pyrophosphate a-δ-galactopyranosyl ester
  • Uridine pyrophosphate alpha-D-galactopyranosyl ester
  • Uridine pyrophosphate alpha-delta-galactopyranosyl ester
  • Uridine pyrophosphate α-D-galactopyranosyl ester
  • Uridine pyrophosphate α-δ-galactopyranosyl ester
  • Uridine pyrophosphogalactose
  • Uridine pyrophosphoric acid a-D-galactopyranosyl ester
  • Uridine pyrophosphoric acid a-delta-galactopyranosyl ester
  • Uridine pyrophosphoric acid a-δ-galactopyranosyl ester
  • Uridine pyrophosphoric acid alpha-D-galactopyranosyl ester
  • Uridine pyrophosphoric acid alpha-delta-galactopyranosyl ester
  • Uridine pyrophosphoric acid α-D-galactopyranosyl ester
  • Uridine pyrophosphoric acid α-δ-galactopyranosyl ester
  • Uridinediphosphate galactose
  • Uridinediphosphogalactose
  • Uridinediphosphoric acid galactose
Chemical Formula:C15H24N2O17P2
Weight:Average: 566.3018
Monoisotopic: 566.055020376
InChI Key:HSCJRCZFDFQWRP-ABVWGUQPSA-N
InChI: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-/m1/s1
CAS number:2956-16-3
IUPAC Name:[({[(2S,3R,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional IUPAC Name:udp galactose
SMILES:OC[C@H]1O[C@H](O[P@@](O)(=O)O[P@@](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
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
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility15.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity106.46 m3·mol-1ChemAxon
Polarizability46.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Water + Uridine diphosphategalactose > Galactose 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
Galactose 1-phosphate + UDP-Glucose <> Glucose 1-phosphate + Uridine diphosphategalactose
UDP-Glucose <> Uridine diphosphategalactose
Uridine diphosphategalactose > UDP-D-Galacto-1,4-furanose
UDP-Glucose <> Uridine diphosphategalactose
UDP-Glucose + Galactose 1-phosphate <> Glucose 1-phosphate + Uridine diphosphategalactose
GDP-L-Fucose + UDP-Glucose + Uridine diphosphate glucuronic acid + Uridine diphosphategalactose colanic acid
UDP-Glucose + Galactose 1-phosphate <> Glucose 1-phosphate + Uridine diphosphategalactose
Uridine diphosphategalactose <> UDP-D-Galacto-1,4-furanose
Glucosyl-heptosyl3-KDO2-lipid A-bisphosphate + Uridine diphosphategalactose > Hydrogen ion + Galactosyl-glucosyl-heptosyl3-KDO2-lipid A-bisphosphate + Uridine 5'-diphosphate
UDP-Glucose <> Uridine diphosphategalactose
UDP-Glucose + Galactose 1-phosphate > Alpha-D-glucose 1-phosphate + Uridine diphosphategalactose
UDP-Glucose > Uridine diphosphategalactose
Uridine diphosphategalactose > UDP-D-Galacto-1,4-furanose
Uridine diphosphategalactose + LPS (1-O-antigen) > Uridine 5'-diphosphate + 3-alpha-D-galactosyl-[lipopolysaccharide glucose]
Uridine diphosphategalactose <> UDP-D-Galacto-1,4-furanose
Uridine diphosphategalactose + LPS (1-O-antigen) <> Uridine 5'-diphosphate + 3-alpha-D-Galactosyl-[lipopolysaccharide glucose]
UDP-Glucose > Uridine diphosphategalactose + Uridine diphosphategalactose
Galactose 1-phosphate + UDP-Glucose + Galactose 1-phosphate > Uridine diphosphategalactose + Glucose 1-phosphate + Uridine diphosphategalactose
UDP-Glucose <> Uridine diphosphategalactose + Uridine diphosphategalactose
SMPDB Pathways:
Galactose metabolismPW000821 Pw000821Pw000821 greyscalePw000821 simple
Lipopolysaccharide biosynthesisPW000831 Pw000831Pw000831 greyscalePw000831 simple
colanic acid building blocks biosynthesisPW000951 Pw000951Pw000951 greyscalePw000951 simple
galactose degradation/Leloir PathwayPW000884 Pw000884Pw000884 greyscalePw000884 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-6c037aa970011034c5a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-734a37a96c862a8e30c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4900000000-b1fed7958b6d958f550eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0i03-4602290000-a6076df9eebf6fe2b2a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-8907020000-11c874a9b28e8fb6a061View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-4901000000-c7008d12e9a99d280f1bView in MoNA
References
References:
  • Holton, J. B. (1990). "Galactose disorders: an overview." J Inherit Metab Dis 13:476-486. Pubmed: 2122114
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Takeda, Satoshi; Noguchi, Toshitada. Enzymic manufacture of 5'-uridine diphosphate galactose (UDP-Gal) from UMP. Jpn. Kokai Tokkyo Koho (2001), 9 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18307
HMDB IDHMDB00302
Pubchem Compound ID18068
Kegg IDC00052
ChemSpider ID17069
WikipediaUDP-galactose
BioCyc IDUDP-GALACTOSE
EcoCyc IDUDP-GALACTOSE

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:
ushA
Uniprot ID:
P07024
Molecular weight:
60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
General function:
Involved in catalytic activity
Specific function:
UDP-glucose = UDP-galactose
Gene Name:
galE
Uniprot ID:
P09147
Molecular weight:
37265
Reactions
UDP-glucose = UDP-galactose.
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:
galT
Uniprot ID:
P09148
Molecular weight:
39645
Reactions
UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose.
General function:
Involved in nucleotide binding
Specific function:
Involved in the conversion of UDP-GalP into UDP-GalF through a 2-keto intermediate
Gene Name:
glf
Uniprot ID:
P37747
Molecular weight:
42966
Reactions
UDP-D-galactopyranose = UDP-D-galacto-1,4-furanose.
General function:
Involved in biosynthetic process
Specific function:
Adds a galactose goup to a glucose group of LPS
Gene Name:
rfaB
Uniprot ID:
P27127
Molecular weight:
40826
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for galactoside. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
mglC
Uniprot ID:
P23200
Molecular weight:
35550
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
UDP-galactose + lipopolysaccharide = UDP + 3- alpha-D-galactosyl-[lipopolysaccharide glucose]
Gene Name:
rfaI
Uniprot ID:
P27128
Molecular weight:
39423
Reactions
UDP-galactose + lipopolysaccharide = UDP + 3-alpha-D-galactosyl-[lipopolysaccharide glucose].

Transporters

General function:
Involved in transporter activity
Specific function:
Responsible for melibiose transport. It is capable of using hydrogen, sodium, and lithium cations as coupling cations for cotransport, depending on the particular sugar transported (symport system)
Gene Name:
melB
Uniprot ID:
P02921
Molecular weight:
52217
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs. Can transport IPTG, lactose and glucose. Has broad substrate specificity, with preferences for glucosides or galactosides with alkyl or aryl substituents
Gene Name:
setA
Uniprot ID:
P31675
Molecular weight:
42713
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for galactoside. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
mglC
Uniprot ID:
P23200
Molecular weight:
35550
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368