Record Information
Version1.0
Creation date2015-10-09 22:33:10 UTC
Update date2017-01-19 02:36:39 UTC
FoodComEx IDPC000869
FoodDB RecordFDB007509
Chemical Information
NameUridine diphosphate
DescriptionUridine 5'-diphosphate, also known as 5'-UDP or uridine diphosphoric acid, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. Uridine 5'-diphosphate is an important extracellular pyrimidine signaling molecule that mediates diverse biological effects via P1 and P2 purinergic receptors, such as the uptake of thymidine and proliferation of gliomas. Uridine 5'-diphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine 5'-diphosphate exists in all living species, ranging from bacteria to humans. Within humans, uridine 5'-diphosphate participates in a number of enzymatic reactions. In particular, tamoxifen-N-glucuronide and uridine 5'-diphosphate can be biosynthesized from tamoxifen and uridine diphosphate glucuronic acid through the action of the enzyme UDP-glucuronosyltransferase 1-4. In addition, 4-hydroxytamoxifen-O-glucuronide and uridine 5'-diphosphate can be biosynthesized from 4-hydroxytamoxifen and uridine diphosphate glucuronic acid through the action of the enzyme UDP-glucuronosyltransferase 1-4. In humans, uridine 5'-diphosphate is involved in tamoxifen metabolism pathway. Outside of the human body, Uridine 5'-diphosphate has been detected, but not quantified in, several different foods, such as pineapples, pine nuts, potato, swiss chards, and lima beans. This could make uridine 5'-diphosphate a potential biomarker for the consumption of these foods.
CAS Number58-98-0
Structure
Thumb
Synonyms
SynonymSource
5'-UDPHMDB
UDPHMDB
Uridine 5'-(trihydrogen diphosphate) (9CI)biospider
Uridine 5'-(trihydrogen pyrophosphate) (8CI)biospider
Uridine 5'-diateChEBI
Uridine 5'-diic acidGenerator
Uridine 5'-diphosphatebiospider
Uridine 5'-diphosphic acidbiospider
Uridine 5'-pyroateHMDB
Uridine 5'-pyroorateHMDB
Uridine 5'-pyrooric acidHMDB
Uridine 5'-pyrophosphatebiospider
Uridine 5'-pyrophosphoratebiospider
Uridine 5'-pyrophosphoric acidbiospider
Uridine diateChEBI
Uridine diic acidGenerator
Uridine diphosphate (6CI)biospider
Uridine pyroateHMDB
Uridine pyrophosphate (7CI)biospider
URIDINE-5'-DIPHOSPHATEbiospider
Uridine, 5'-(trihydrogen diphosphate)biospider
Chemical FormulaC9H14N2O12P2
IUPAC name[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
InChI IdentifierInChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
InChI KeyXCCTYIAWTASOJW-XVFCMESISA-N
Isomeric SMILESO[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O
Average Molecular Weight404.1612
Monoisotopic Molecular Weight404.002196946
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct ParentPyrimidine ribonucleoside diphosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Hydroxypyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 10 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci V1660