Uridin-5'-(trihydrogen-diphosphat), Mono-α-D-glucopyranosylester

Udp-Glucose

HCID 8629CAS 133-89-1

Teilstruktursuche Ähnliche Strukturen suchen

Grundinformationen

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
Summenformel: C15H24N2O17P2
Durchschnittliche Molmasse: 566,3 g/mol
Monoisotopische Masse: 566,05502057

Überblick

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-).

Namen und Bezeichner

Bevorzugter 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
Lokaler Name: Uridin-5'-(trihydrogen-diphosphat), Mono-α-D-glucopyranosylester
Englischer Name: Uridine 5'-(trihydrogen diphosphate), mono-alpha-d-glucopyranosyl ester
Summenformel: C15H24N2O17P2
Molmasse: 566.3

Namen und Synonyme

UDP-glucoseURIDINE DIPHOSPHATE GLUCOSE133-89-1UDPGUridine diphosphoglucoseco-waldenaseUDPglucoseco-galactoisomeraseCogalactoisomeraseUDP glucoseDiphosphate Glucose, Uridine5'-Diphosphoglucose

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -6,3
Polarare Oberfläche (TPSA): 292 Å²
H-Brücken-Donoren: 9
H-Brücken-Akzeptoren: 17
Frei drehbare Bindungen: 9
Schwere Atome: 36
Formalladung: 0
Komplexität: 964

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Physical DescriptionSolid

Collision Cross Section · 3 Einträge

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]-

Physikochemische Eigenschaften

storage temp.: -20 °C, · Store at -20°C, protect from light, stored under nitrogen
Löslichkeit: Easily soluble (water), soluble (methanol), insoluble ((CH3)2CO, (C2H5)2O)
Aggregatzustand: Solid
Dichte: 1.97 · 1.97±0.1 g/cm3(Predicted)
pka: 1.1 · 1.10±0.50(Predicted)
Farbe: White to off-white
Wasserlöslichkeit: 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

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsLiver

Cellular LocationsEndoplasmic reticulum

Metabolite PathwaysCongenital disorder of glycosylation CDG-IId

Anwendungen · 1 Eintrag

BeschreibungAn 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.