Udp-Glucose

HCID 8629CAS 133-89-1

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Basic information

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: 566.05502057

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

Database identifiers

CAS: 133-89-1
PubChem CID: 8629
DTXSID: DTXSID00157902
ChEMBL: CHEMBL375951
ChEBI: CHEBI:46229
UNII: V50K1D7P4Y
EC Number: 205-121-4
Nikkaji: J9.610E

Properties

Computed structural properties

XLogP: -6.3
Topological polar surface area: 292 Å²
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 · 3 items

209.2 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

210.5 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

207.3 Å² [M-H]-

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: HSCJRCZFDFQWRP-JZMIEXBBSA-N
SMILES: O[C@@H]1[C@@H]([C@H](O[C@H]1N1C=CC(NC1=O)=O)COP(O)(=O)OP(O)(=O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O
FDA UNII: 50 K1D7P4Y · V50K1D7P4Y

Chemistry & industry

Pharmacology

Tissue LocationsLiver

Cellular LocationsEndoplasmic reticulum

Metabolite PathwaysCongenital disorder of glycosylation CDG-IId

Applications · 2 items

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

Suppliers50 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]

Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]

湖北威德利化学试剂有限公司181-6332-1995 18062128043 · [email protected]

上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

Additional notes

DefinitionChEBI: 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-).