Common NameUdp-alpha-d-glucose
DescriptionUridine diphosphate glucose, also known as UDP-glucose or UDP-alpha-D-glucose, 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. Uridine diphosphate glucose exists in all living species, ranging from bacteria to plants to humans. Uridine diphosphate glucose is a key intermediate in carbohydrate metabolism. For instance, UDP-glucose is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid. UDP-glucose can also be used as a precursor for the biosynthesis of sucrose, lipopolysaccharides and glycosphingolipids. Within humans, uridine diphosphate glucose participates in a number of enzymatic reactions. In particular, ceramide (D18:1/18:0) and uridine diphosphate glucose can be converted into glucosylceramide (D18:1/18:0) and uridine 5'-diphosphate through the action of the enzyme ceramide glucosyltransferase. In addition, glucosylceramide (D18:1/18:0) and uridine diphosphate glucose can be biosynthesized from lactosylceramide (D18:1/18:0) and uridine 5'-diphosphate through its interaction with the enzyme Beta-1,4-galactosyltransferase 6.
Structure
Molecular FormulaC15H24N2O17P2
Average Mass566.30180
Monoisotopic Mass566.05502
IUPAC Name[({[(2S,3R,4S,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional Name{[(2s,3r,4s,5s)-5-(2,4-dioxo-3h-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphinic acid
CAS Registry Number133-89-1
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-JZMIEXBBSA-N
CHEBI IDCHEBI:58885
HMDB IDHMDB0000286
Pathways
NameSMPDB/PathBank
Starch and sucrose metabolism
Nucleotide Sugars Metabolism
Galactose Metabolism
Starch and Sucrose Metabolism
Galactosemia
Metachromatic Leukodystrophy (MLD)
Globoid Cell Leukodystrophy
Gaucher Disease
Lactose Synthesis
Galactosemia II (GALK)
Galactosemia III
Fabry disease
Krabbe disease
Glycogen synthetase deficiency
Glycogenosis, Type III. Cori disease, Debrancher glycogenosis
Glycogenosis, Type IV. Amylopectinosis, Anderson disease
Glycogenosis, Type VI. Hers disease
Mucopolysaccharidosis VI. Sly syndrome
Sucrase-isomaltase deficiency
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
Polarizability46.50

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