Record Information
Version2.0
Creation Date2015-09-08 17:50:12 -0600
Update Date2015-09-14 16:46:01 -0600
Secondary Accession Numbers
  • ECMDB24224
Identification
Name:UDP-α-D-galactose
DescriptionUDP-α-D-galactose (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:
ValueSource
UDP GalactoseChEBI
UDP-alpha-D-GalactopyranoseChEBI
UDP-D-GalactopyranoseChEBI
UDP-GalactoseChEBI
Uridine diphosphate galactoseChEBI
Uridine diphosphogalactoseChEBI
Uridine pyrophosphogalactoseChEBI
UridinediphosphogalactoseChEBI
UDP-a-D-GalactopyranoseGenerator
UDP-α-D-galactopyranoseGenerator
Uridine diphosphoric acid galactoseGenerator
GDUHMDB
UDP-a-D-GalactoseHMDB
UDP-alpha-D-GalactoseHMDB
UDP-D-galactoseHMDB
UDP-D-GalactoseHMDB
UDP-GalHMDB
UDP-galactopyranoseHMDB
UdpgalHMDB, MeSH
UDPgalactoseHMDB
UPGHMDB
Uridine 5'-(alpha-D-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 alpha-D-galactosyl esterHMDB
Uridine 5'-pyrophosphate D-galactosyl esterHMDB
Uridine 5'-[3-(D-galactopyranosyl) dihydrogen diphosphate]HMDB
Uridine diphosphate-D-galactoseHMDB
Uridine diphosphate-galactoseHMDB
Uridine pyrophosphate a-D-galactopyranosyl esterHMDB
Uridine pyrophosphate alpha-D-galactopyranosyl esterHMDB
Uridinediphosphate galactoseHMDB
Diphosphate galactose, uridineMeSH, HMDB
Diphosphogalactose, uridineMeSH, HMDB
Galactose, UDPMeSH, HMDB
Galactose, uridine diphosphateMeSH, HMDB
Pyrophosphogalactose, uridineMeSH, HMDB
UDP-α-D-GalactoseHMDB
Uridine 5'-(α-D-galactopyranosyl pyrophosphate)HMDB
Uridine 5’-(α-D-galactopyranosyl pyrophosphate)HMDB
Uridine 5’-diphosphate galactoseHMDB
Uridine 5’-diphosphogalactoseHMDB
Chemical Formula:C15H22N2O17P2
Weight:Average: 564.287
Monoisotopic: 564.040468412
InChI Key:HSCJRCZFDFQWRP-LNYDKVEPSA-L
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)/p-2/t5-,6-,8+,9-,10+,11-,12-,13-,14?/m1/s1
CAS number:Not Available
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 IUPAC 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]oxy)phosphinic acid
SMILES:OC[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
  • Hydroxypyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Primary alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability45.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
O-antigen building blocks biosynthesisPW002089 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-3933570000-89f658b2d26ff158d84cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fk9-4942706000-3a83736296429f83adeeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Uridine diphosphategalactose,1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0100-9428070000-ad4101fafd847dad3677View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9542000000-d123218d2da9e69639c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1019070000-115705199f12c6ee31ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-d2ad622dfdfc17d6f2bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-0009000000-d87f68f0d87b8ad5ad67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901110000-4b81825405869909992eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3911000000-6fd09254750e77963110View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5900000000-03a2a98eb0aa84737530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4901260000-8396a090c14de7f2d708View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-8907020000-94410556a0288cb8167bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5901000000-10132c85ad33464d4eefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0000960000-6404d8d944e1ae6f30e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07e1-2322960000-6af539ce21752f9023baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9732000000-b0c81adc41b1d799e1e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-8cab8f2bc0fb9e9e8ba9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057j-9203870000-d60681ff91f741bdb867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3519000000-67ca2f9355ef7f94a47dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID67119
HMDB IDHMDB0000302
Pubchem Compound ID18068
Kegg IDC00052
ChemSpider ID17069
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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