Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:42:48 UTC
Update Date2022-08-31 17:18:44 UTC
Metabolite IDMMDBc0029813
Metabolite Identification
Common NameUDP-D-Galacto-1,4-furanose
DescriptionUDP-D-galacto-1,4-furanose is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphogalactofuranose (UDP-Galf) is the precursor of the d-galactofuranose (Galf) residues found in bacterial and parasitic cell walls, including those of many pathogens, such as Mycobacterium tuberculosis and Trypanosoma cruzi. (PMID 11573090 ) UDP-galactopyranose mutase (UGM) is a flavin-containing enzyme that catalyzes the conversion of UDP-galactopyranose to UDP-galactofuranose, the precursor of galactofuranose, which is an important cell wall component in Aspergillus fumigatus and other pathogenic microbes. (PMID 20615386 )
Structure
Synonyms
ValueSource
UDP-alpha-D-Galacto-1,4-furanoseChEBI
UDP-a-D-Galacto-1,4-furanoseGenerator
UDP-Α-D-galacto-1,4-furanoseGenerator
UDP-GalactofuranoseMeSH
Uridine diphosphate galactofuranoseMeSH
UDP-Gal(F)MeSH
Molecular FormulaC15H24N2O17P2
Average Mass566.3018
Monoisotopic Mass566.055020376
IUPAC Name[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy})phosphinic acid
Traditional Nameudp-D-galacto-1,4-furanose
CAS Registry Number638-23-3
SMILES
[H][C@@](O)(CO)[C@]1([H])O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]([H])(O)[C@@]1([H])O
InChI Identifier
InChI=1S/C15H24N2O17P2/c18-3-5(19)12-9(22)11(24)14(32-12)33-36(28,29)34-35(26,27)30-4-6-8(21)10(23)13(31-6)17-2-1-7(20)16-15(17)25/h1-2,5-6,8-14,18-19,21-24H,3-4H2,(H,26,27)(H,28,29)(H,16,20,25)/t5-,6-,8-,9-,10-,11-,12+,13-,14-/m1/s1
InChI KeyZQLQOXLUCGXKHS-SIAUPFDVSA-N