Udp-Glucose
Basic information
- CAS
133-89-1- Standard SMILES
O=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- InChIKey
HSCJRCZFDFQWRP-JZMIEXBBSA-N- Molecular formula
- C15H24N2O17P2
- Average molar mass
- 566.3 g/mol
- Monoisotopic mass
- 566.0550213
Overview
UDP-alpha-D-glucose is the alpha-anomer of UDP-alpha-D-glucose. It is used in nucleotide sugars metabolism. It has a role as a fundamental metabolite. It is a conjugate acid of an UDP-alpha-D-glucose(2-).
Names & identifiers
- Preferred name
- Udp-Glucose
- IUPAC
- [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
- English name
- Uridine 5'-(trihydrogen diphosphate), mono-alpha-d-glucopyranosyl ester
- Molecular formula
- C15H24N2O17P2
- Molecular weight
- 566.3
Names & synonyms
UDP-glucoseURIDINE DIPHOSPHATE GLUCOSE133-89-1UDPGUridine diphosphoglucoseco-waldenaseUDPglucoseco-galactoisomeraseCogalactoisomeraseUDP glucoseDiphosphate Glucose, Uridine5'-Diphosphoglucose
Show more names
UDP-D-glucoseUDP-a-D-GlucoseUridine-5''-diphospho-D-glucoseUridine 5'-pyrophosphate, D-glucosyl esteruridine(5')dihydrogendiphospho(1)-alpha-D-glucose5-triphosphate hydrogen - β - D-glucopyranose uridineUridine 5'-diphosphoric acid β-(α-D-glucopyranosyl) ester
Uridine 5'-pyrophosphate glucose esterV50K1D7P4Y[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphateDTXSID00157902URIDINE-5'-DIPHOSPHOGLUCOSEUridine 5'-(trihydrogen diphosphate), P'-alpha-D-glucopyranosyl esterGlucose, UDPDiphosphoglucose, Uridine
Properties
Computed structural properties
- XLogP
- -6.3
- Topological polar surface area
- 292 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 17
- Rotatable bonds
- 9
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 964
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionSolid
Collision Cross Section
209.2 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
210.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
216.4 Ų [M+K]+
Physicochemical properties
- storage temp.
- -20 °C, · Store at -20°C, protect from light, stored under nitrogen
- solubility
- Easily soluble (water), soluble (methanol), insoluble ((CH3)2CO, (C2H5)2O)
- form
- Solid
- Density
- 1.97 · 1.97±0.1 g/cm3(Predicted)
- pka
- 1.1 · 1.10±0.50(Predicted)
- color
- White to off-white
- Water Solubility
- 50 mg/mL · Water : ≥ 50 mg/mL
- InChIKey
Chemistry & industry
Pharmacology
Tissue LocationsLiver
Cellular LocationsEndoplasmic reticulum
Metabolite PathwaysCongenital disorder of glycosylation CDG-IId
Applications
DescriptionAn intermediate in the phase II reaction that results in the formation of glucose conjugates of xenobiotics which contain substituents such as hydroxyl, amino or sulfhydryl groups, the O-, N-, and S-glucosides, respectively. UDPG is formed from uridine triphosphate and glucose-1- phosphate in a reaction catalyzed by the enzyme UDPG pyro_x0002_phosphorylase. Glucoside formation is common in insects and plants, whereas animals other than insects utilize uridine diphosphate glucuronic acid to form glucuronides.
UsesUridine diphosphate glucose (Standard) is the analytical standard of Uridine diphosphate glucose. This product is intended for research and analytical applications. Uridine diphosphate glucose is the precursor of glucose-containing oligosaccharides, polysaccharides, glycoproteins, and glycolipids in animal tissues and in some microorganisms. Uridine diphosphate glucose is an agonist of the P2Y14 receptor, a neuroimmune system GPCR.
Upstream & downstream products
Downstream products
Related reactions
13 records
Compound notes
Loading…