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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:32 UTC
HMDB IDHMDB00302
Secondary Accession NumbersNone
Metabolite Identification
Common NameUridine diphosphategalactose
DescriptionUridine 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). Defective galactosylation of complex glycoconjugates exists in tissues from galactosemic patients. There is a tendency for galactosemic red cell UDPgal to be in the low normal range with a high uridine diphosphate glucose to UDP-gal ratio. This may reflect an inability of red cell UDPgal-4'-epimerase to maintain a normal ratio and consequently higher levels of UDPgal. In the more complex white blood cells and cultured fibroblasts, the UDPgal content and the uridine diphosphate glucose to UDPgal ratio of galactosemics are normal. Therefore, defective galactosylation observed in galactosemic fibroblasts must result from a defect in the transfer of galactose from UDPgal to these moieties. (PMID: 2122114 , 7671968 ).
Structure
Thumb
Synonyms
ValueSource
UDP GalactoseChEBI
UDP-alpha-D-GalactopyranoseChEBI
UDP-D-GalactopyranoseChEBI
UDP-GalactoseChEBI
Uridine diphosphate galactoseChEBI
Uridine diphosphogalactoseChEBI
Uridine pyrophosphogalactoseChEBI
UridinediphosphogalactoseChEBI
UDP-a-D-GalactoseGenerator
UDP-α-D-galactoseGenerator
UDP-a-D-GalactopyranoseGenerator
UDP-α-D-galactopyranoseGenerator
Uridine diphosphoric acid galactoseGenerator
GDUHMDB
UDP-alpha-delta-GalactoseHMDB
UDP-D-GalactoseHMDB
UDP-delta-GalactopyranoseHMDB
UDP-delta-GalactoseHMDB
UDP-GalHMDB
UDP-GalactopyranoseHMDB
UdpgalHMDB
UDPgalactoseHMDB
UPGHMDB
Uridine 5'-(alpha-D-galactopyranosyl pyrophosphate)HMDB
Uridine 5'-(alpha-delta-galactopyranosyl pyrophosphate)HMDB
Uridine 5'-diphosphate galactoseHMDB
Uridine 5'-diphosphogalactoseHMDB
Uridine 5'-pyrophosphate a-D-galactopyranosyl esterHMDB
Uridine 5'-pyrophosphate a-D-galactosyl esterHMDB
Uridine 5'-pyrophosphate a-delta-galactopyranosyl esterHMDB
Uridine 5'-pyrophosphate a-delta-galactosyl esterHMDB
Uridine 5'-pyrophosphate alpha-D-galactosyl esterHMDB
Uridine 5'-pyrophosphate alpha-delta-galactosyl esterHMDB
Uridine 5'-pyrophosphate D-galactosyl esterHMDB
Uridine 5'-[3-(D-galactopyranosyl) dihydrogen diphosphate]HMDB
Uridine diphosphate-D-galactoseHMDB
Uridine diphosphate-delta-galactoseHMDB
Uridine diphosphate-galactoseHMDB
Uridine pyrophosphate a-D-galactopyranosyl esterHMDB
Uridine pyrophosphate a-delta-galactopyranosyl esterHMDB
Uridine pyrophosphate alpha-D-galactopyranosyl esterHMDB
Uridine pyrophosphate alpha-delta-galactopyranosyl esterHMDB
Uridinediphosphate galactoseHMDB
Chemical FormulaC15H24N2O17P2
Average Molecular Weight566.3018
Monoisotopic Molecular Weight566.055020376
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]({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional Name{[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphinic acid
CAS Registry Number2956-16-3
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
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-/m1/s1
InChI KeyInChIKey=HSCJRCZFDFQWRP-ABVWGUQPSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Secondary alcohol
  • Polyol
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Galactose metabolism
  • Component of Ganglioside biosynthesis
  • Component of Globoside metabolism
  • Component of Keratan sulfate biosynthesis
  • Component of N-Glycan biosynthesis
  • Component of Nucleotide sugars metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Golgi apparatus
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 Solubility15.0 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
Polarizability45.05 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0100-9428070000-ad4101fafd847dad3677View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Golgi apparatus
Biofluid Locations
  • Urine
Tissue Location
  • Liver
  • Most Tissues
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Congenital disorder of glycosylation CDG-IIdSMP00579Not Available
Galactose MetabolismSMP00043map00052
GalactosemiaSMP00182Not Available
Galactosemia II (GALK)SMP00495Not Available
Galactosemia IIISMP00496Not Available
GLUT-1 deficiency syndromeSMP00580Not Available
Lactose SynthesisSMP00444Not Available
Nucleotide Sugars MetabolismSMP00010map00520
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified2.008 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021811
KNApSAcK IDNot Available
Chemspider ID17069
KEGG Compound IDC00052
BioCyc IDUDP-GLACTOSE
BiGG ID33675
Wikipedia LinkUDP-galactose
NuGOwiki LinkHMDB00302
Metagene LinkHMDB00302
METLIN ID5291
PubChem Compound18068
PDB IDGDU
ChEBI ID67119
References
Synthesis ReferenceTakeda, 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)
General References
  1. Ng WG, Xu YK, Kaufman FR, Donnell GN: Deficit of uridine diphosphate galactose in galactosaemia. J Inherit Metab Dis. 1989;12(3):257-66. [2515367 ]
  2. Matsukura Y: Alpha-galactosyltransferase activity in the serum of frogs (Rana catesbeiana). Z Immunitatsforsch Immunobiol. 1976 Nov;152(3):260-5. [1087514 ]
  3. Keevill NJ, Holton JB, Allen JT: UDP-glucose and UDP-galactose concentrations in cultured skin fibroblasts of patients with classical galactosaemia. J Inherit Metab Dis. 1994;17(1):23-6. [8051935 ]
  4. Matsukura Y: On the blood group B gene-specified alpha-galactosyltransferase in the serum of the Japanese tortoise (Clemmys japonica). Immunology. 1976 Oct;31(4):571-5. [977033 ]
  5. Hoffmeister KM, Josefsson EC, Isaac NA, Clausen H, Hartwig JH, Stossel TP: Glycosylation restores survival of chilled blood platelets. Science. 2003 Sep 12;301(5639):1531-4. [12970565 ]
  6. Holton JB: Galactose disorders: an overview. J Inherit Metab Dis. 1990;13(4):476-86. [2122114 ]
  7. Segal S: Defective galactosylation in galactosemia: is low cell UDPgalactose an explanation? Eur J Pediatr. 1995;154(7 Suppl 2):S65-71. [7671968 ]

Enzymes

General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids. Can produce lactose.
Gene Name:
B4GALT2
Uniprot ID:
O60909
Molecular weight:
41971.815
Reactions
Uridine diphosphategalactose + D-Glucose → Uridine 5'-diphosphate + beta-Lactosedetails
Uridine diphosphategalactose + N-acetyl-beta-D-glucosaminylglycopeptide → Uridine 5'-diphosphate + beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminylglycopeptidedetails
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
General function:
Involved in lactose synthase activity
Specific function:
Regulatory subunit of lactose synthase, changes the substrate specificity of galactosyltransferase in the mammary gland making glucose a good acceptor substrate for this enzyme. This enables LS to synthesize lactose, the major carbohydrate component of milk. In other tissues, galactosyltransferase transfers galactose onto the N-acetylglucosamine of the oligosaccharide chains in glycoproteins.
Gene Name:
LALBA
Uniprot ID:
P00709
Molecular weight:
Not Available
Reactions
Uridine diphosphategalactose + D-Glucose → Uridine 5'-diphosphate + beta-Lactosedetails
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids. The cell surface form functions as a recognition molecule during a variety of cell to cell and cell to matrix interactions, as those occurring during development and egg fertilization, by binding to specific oligosaccharide ligands on opposing cells or in the extracellular matrix.
Gene Name:
B4GALT1
Uniprot ID:
P15291
Molecular weight:
43919.895
Reactions
Uridine diphosphategalactose + D-Glucose → Uridine 5'-diphosphate + beta-Lactosedetails
Uridine diphosphategalactose + N-acetyl-beta-D-glucosaminylglycopeptide → Uridine 5'-diphosphate + beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminylglycopeptidedetails
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
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 diphosphategalactose + Procollagen 5-hydroxy-L-lysine → Uridine 5'-diphosphate + 5-(D-Galactosyloxy)-L-lysine-procollagendetails
General function:
Involved in galactosyltransferase activity
Specific function:
Necessary for the biosynthesis of the Pk antigen of blood histogroup P. Catalyzes the transfer of galactose to lactosylceramide and galactosylceramide. Necessary for the synthesis of the receptor for bacterial verotoxins.
Gene Name:
A4GALT
Uniprot ID:
Q9NPC4
Molecular weight:
40498.78
Reactions
Uridine diphosphategalactose + beta-D-galactosyl-(1->4)-D-glucosyl-(1<->1)-ceramide → Uridine 5'-diphosphate + alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-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
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:
B4GALT3
Uniprot ID:
O60512
Molecular weight:
43927.63
Reactions
Uridine diphosphategalactose + N-acetyl-beta-D-glucosaminylglycopeptide → Uridine 5'-diphosphate + beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminylglycopeptidedetails
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:
B4GALT4
Uniprot ID:
O60513
Molecular weight:
40040.865
Reactions
Uridine diphosphategalactose + N-Acetyl-D-glucosamine → Uridine 5'-diphosphate + N-Acetyllactosaminedetails
Uridine diphosphategalactose + N-acetyl-beta-D-galactosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide → Uridine 5'-diphosphate + beta-D-galactosyl-(1->4)-N-acetyl-beta-D-galactosaminyl-(1->3)-beta-D-galactosyl-(1->4)--D-glucosyl-(1<->1)-ceramidedetails
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 hexosyl groups
Specific function:
This protein is the basis of the ABO blood group system. The histo-blood group ABO involves three carbohydrate antigens: A, B, and H. A, B, and AB individuals express a glycosyltransferase activity that converts the H antigen to the A antigen (by addition of UDP-GalNAc) or to the B antigen (by addition of UDP-Gal), whereas O individuals lack such activity.
Gene Name:
ABO
Uniprot ID:
P16442
Molecular weight:
40933.555
Reactions
Uridine diphosphategalactose + alpha-L-fucosyl-(1->2)-D-galactosyl-R → Uridine 5'-diphosphate + alpha-D-galactosyl-(1->3)-(alpha-L-fucosyl-(1->2))-D-galactosyl-Rdetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Catalyzes the transfer of galactose to ceramide, a key enzymatic step in the biosynthesis of galactocerebrosides, which are abundant sphingolipids of the myelin membrane of the central nervous system and peripheral nervous system.
Gene Name:
UGT8
Uniprot ID:
Q16880
Molecular weight:
61455.31
Reactions
Uridine diphosphategalactose + 2-(2-hydroxyacyl)sphingosine → Uridine 5'-diphosphate + 1-(beta-D-galactosyl)-2-(2-hydroxyacyl)sphingosinedetails
Uridine diphosphategalactose + N-Acylsphingosine → Uridine 5'-diphosphate + Galactosylceramidedetails
General function:
Involved in galactosyltransferase activity
Specific function:
Involved in GM1/GD1B/GA1 ganglioside biosynthesis.
Gene Name:
B3GALT4
Uniprot ID:
O96024
Molecular weight:
41536.435
Reactions
Uridine diphosphategalactose + an N-acetyl-beta-D-galactosaminyl-(1->4)-(alpha-N-acetylneuraminyl-(2->3))-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide → Uridine 5'-diphosphate + a beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)-(alpha-N-acetylneuraminyl-(2->3))-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramidedetails
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Required for the biosynthesis of the tetrasaccharide linkage region of proteoglycans, especially for small proteoglycans in skin fibroblasts.
Gene Name:
B4GALT7
Uniprot ID:
Q9UBV7
Molecular weight:
37405.53
Reactions
Uridine diphosphategalactose + O-beta-D-xylosyl-[protein] → Uridine 5'-diphosphate + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein]details
General function:
Involved in galactosyltransferase activity
Specific function:
Beta-1,3-galactosyltransferase that transfers galactose from UDP-galactose to substrates with a terminal beta-linked galactose residue. Has a preference for galactose-beta-1,4-xylose that is found in the linker region of glycosaminoglycans, such as heparan sulfate and chondroitin sulfate. Has no activity towards substrates with terminal glucosamine or galactosamine residues.
Gene Name:
B3GALT6
Uniprot ID:
Q96L58
Molecular weight:
37137.08
Reactions
Uridine diphosphategalactose + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein] → Uridine 5'-diphosphate + 3-beta-D-galactosyl-4-beta-D-galactosyl-O-beta-D-xylosyl-[protein]details
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Glycosyltransferase that generates the core 1 O-glycan Gal-beta1-3GalNAc-alpha1-Ser/Thr (T antigen), which is a precursor for many extended O-glycans in glycoproteins. Plays a central role in many processes, such as angiogenesis, thrombopoiesis and kidney homeostasis development.
Gene Name:
C1GALT1
Uniprot ID:
Q9NS00
Molecular weight:
42202.5
Reactions
Uridine diphosphategalactose + glycoprotein N-acetyl-D-galactosamine → Uridine 5'-diphosphate + glycoprotein D-galactosyl-(1->3)-N-acetyl-D-galactosaminedetails
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Required for the biosynthesis of glycosphingolipids.
Gene Name:
B4GALT6
Uniprot ID:
Q9UBX8
Molecular weight:
44913.315
Reactions
Uridine diphosphategalactose + beta-D-glucosyl-(1<->1)-ceramide → Uridine 5'-diphosphate + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramidedetails
beta-D-Glucosyl-(1<->1)-ceramide + Uridine diphosphategalactose → beta-D-Galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide + Uridine 5'-diphosphatedetails
General function:
Not Available
Specific function:
Has a beta-galactosyltransferase activity; transfers beta-galactose to hydroxylysine residues of collagen.
Gene Name:
GLT25D1
Uniprot ID:
Q8NBJ5
Molecular weight:
71635.385
Reactions
Uridine diphosphategalactose + 5-hydroxy-L-lysine-[procollagen] → Uridine 5'-diphosphate + 5-(D-galactosyloxy)-L-lysine-[procollagen]details
Uridine diphosphategalactose + Procollagen 5-hydroxy-L-lysine → Uridine 5'-diphosphate + 5-(D-Galactosyloxy)-L-lysine-procollagendetails
General function:
Not Available
Specific function:
Has a beta-galactosyltransferase activity; transfers beta-galactose to hydroxylysine residues on collagen.
Gene Name:
GLT25D2
Uniprot ID:
Q8IYK4
Molecular weight:
72923.665
Reactions
Uridine diphosphategalactose + 5-hydroxy-L-lysine-[procollagen] → Uridine 5'-diphosphate + 5-(D-galactosyloxy)-L-lysine-[procollagen]details
Uridine diphosphategalactose + Procollagen 5-hydroxy-L-lysine → Uridine 5'-diphosphate + 5-(D-Galactosyloxy)-L-lysine-procollagendetails