Showing Metabocard for UDP-alpha-D-galactose (BASm0004786)

Common NameUdp-alpha-d-galactose
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
Molecular FormulaC15H24N2O17P2
Average Mass566.30180
Monoisotopic Mass566.05502
IUPAC Name{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional Name[(2r,3s,4r,5r)-5-(2,4-dioxo-3h-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({hydroxy[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphoryl}oxy)phosphinic acid
CAS Registry Number2956-16-3
SMILESO=c1ccn([C@@H]2O[C@H](COP(=O)([O-])OP(=O)([O-])O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1
InChI IdentifierInChI=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 KeyHSCJRCZFDFQWRP-ABVWGUQPSA-N
CHEBI IDCHEBI:66914
HMDB IDHMDB0000302
Pathways
NameSMPDB/PathBank
Nucleotide Sugars Metabolism
Galactose Metabolism
Galactosemia
Lactose Synthesis
Galactosemia II (GALK)
Galactosemia III
Congenital disorder of glycosylation CDG-IId
GLUT-1 deficiency syndrome
StateSolid
Water Solubility1.50e+01 g/l
logP-1.43
logS-1.58
pKa (Strongest Acidic)1.73
pKa (Strongest Basic)-3.65
Hydrogen Acceptor Count14
Hydrogen Donor Count9
Polar Surface Area291.54 Ų
Rotatable Bond Count9
Physiological Charge-2
Formal Charge0
Refractivity106.46 m³·mol⁻¹
Polarizability45.05

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