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Identification
YMDB IDYMDB00797
Nameudp-galactose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionudp-galactose belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. udp-galactose is an extremely weak basic (essentially neutral) compound (based on its pKa). udp-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'-[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
CAS number2956-16-3
WeightAverage: 566.3018
Monoisotopic: 566.055020376
InChI KeyUSAZACJQJDHAJH-QFIAFIRLSA-N
InChIInChI=1S/C15H24N2O17P2/c18-2-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-3-6-9(21)11(23)13(31-6)4-1-7(19)17-15(25)16-4/h1,5-6,8-14,18,20-24H,2-3H2,(H,26,27)(H,28,29)(H2,16,17,19,25)/t5-,6-,8+,9-,10+,11-,12-,13+,14+/m1/s1
IUPAC Name[({[(2R,3S,4R,5S)-5-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional IUPAC Name{[(2R,3S,4R,5S)-5-(2,6-dioxo-1,3-dihydropyrimidin-4-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphinic acid
Chemical FormulaC15H24N2O17P2
SMILESOC[C@H]1O[C@@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2=CC(=O)NC(=O)N2)[C@H](O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose-5-phosphate
  • Pentose phosphate
  • Glycosyl compound
  • C-glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Urea
  • Secondary alcohol
  • Lactam
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Dialkyl ether
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility12.3 g/LALOGPS
logP-1.5ALOGPS
logP-5.6ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area300.33 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity107.56 m³·mol⁻¹ChemAxon
Polarizability45.77 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Galactose metabolismec00052 Map00052
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n1-0539660000-64d292580b7332771722JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056s-3296010000-47ea0cd7a0ad7053153fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08ic-3911000000-75da2d540b8dfe9e6aa5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-4303290000-9442c91fff5ea98e9ff2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-6509020000-926c41bdf24d90469b31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-5901000000-05e1f8197c9c87c069b2JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
  • DOUGLAS, H. C., HAWTHORNE, D. C. (1964). "ENZYMATIC EXPRESSION AND GENETIC LINKAGE OF GENES CONTROLLING GALACTOSE UTILIZATION IN SACCHAROMYCES." Genetics 49:837-844.14158615
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID693249
HMDB IDHMDB00302
Pubchem Compound ID18068
Kegg IDC00052
ChemSpider ID24655250
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.