UPG

URIDINE-5'-DIPHOSPHATE-GLUCOSE

Created: 1999-07-08
Last modified:  2024-09-27

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Chemical Details

Formal Charge0
Atom Count60
Chiral Atom Count9
Bond Count62
Aromatic Bond Count0
2D diagram of UPG
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Chemical Component Summary

NameURIDINE-5'-DIPHOSPHATE-GLUCOSE
SynonymsURIDINE-5'-MONOPHOSPHATE GLUCOPYRANOSYL-MONOPHOSPHATE ESTER
Systematic Name (OpenEye OEToolkits)[[(2R,3S,4R,5R)-5-[2,4-bis(oxidanylidene)pyrimidin-1-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl] hydrogen phosphate
FormulaC15 H24 N2 O17 P2
Molecular Weight566.302
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C1C=CN(C(=O)N1)C2OC(C(O)C2O)COP(=O)(OP(=O)(OC3OC(C(O)C(O)C3O)CO)O)O
SMILESCACTVS3.370OC[CH]1O[CH](O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=O)NC3=O)[CH](O)[CH](O)[CH]1O
SMILESOpenEye OEToolkits1.7.6C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)CO)O)O)O)O)O
Canonical SMILESCACTVS3.370 OC[C@H]1O[C@H](O[P](O)(=O)O[P](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)[C@H](O)[C@@H](O)[C@@H]1O
Canonical SMILESOpenEye OEToolkits1.7.6 C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO[P@](=O)(O)O[P@](=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
InChIInChI1.03 InChI=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
InChIKeyInChI1.03 HSCJRCZFDFQWRP-JZMIEXBBSA-N

Drug Info: DrugBank

DrugBank IDDB01861 
NameUridine diphosphate glucose
Groups experimental
DescriptionA key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.
Synonyms
  • Uridine 5'-pyrophosphate glucose ester
  • Uridine diphosphate glucose
  • 5'-Diphosphoglucose
  • Co-galactoisomerase
  • UDP-Glucose
Categories
  • Carbohydrates
  • Glycosides
  • Nucleic Acids, Nucleotides, and Nucleosides
  • Nucleoside Diphosphate Sugars
  • Nucleotides
CAS number133-89-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Galactose-1-phosphate uridylyltransferaseMTQFNPVDHPHRRYNPLTGQWILVSPHRAKRPWQGAQETPAKQVLPAHDP...unknown
UDP-glucose 4-epimeraseMAEKVLVTGGAGYIGSHTVLELLEAGYLPVVIDNFHNAFRGGGSLPESLR...unknown
Alpha,alpha-trehalose-phosphate synthase [UDP-forming]MSRLVVVSNRIAPPDEHAASAGGLAVGILGALKAAGGLWFGWSGETGNED...unknown
Glucose-1-phosphate thymidylyltransferaseMKTRKGIILAGGSGTRLYPVTMAVSKQLLPIYDKPMIYYPLSTLMLAGIR...unknown
UDP-glucose 4-epimeraseMRVLVTGGSGYIGSHTCVQLLQNGHDVIILDNLCNSKRSVLPVIERLGGK...unknown
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 8629
ChEMBL CHEMBL375951
ChEBI CHEBI:46229