{[(2R,3R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,4S,5S)-3,4,5-trihydroxy-6-[hydroxy(13C)methyl](2,3,4,5,6-13C5)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid

• ChemBase ID: 179399
• Molecular Formular: C15H24N2O17P2
• Molecular Mass: 572.25771103
• Monoisotopic Mass: 572.07514961
• SMILES: [C@H]1(C([C@@H](O[C@@H]1COP(=O)(OP(=O)(O[13C@H]1O[13CH]([13C@H]([13C@@H]([13CH]1O)O)O)[13CH2]O)O)O)n1c(=O)[nH]c(=O)cc1)O)O
• Canonical SMILES: O[13CH2][13CH]1O[13C@H](OP(=O)(OP(=O)(OC[C@H]2O[C@H](C([C@H]2O)O)n2ccc(=O)[nH]c2=O)O)O)[13CH]([13C@H]([13C@@H]1O)O)O
• InChI: 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/i3+1,5+1,8+1,10+1,12+1,14+1
• InChIKey: HSCJRCZFDFQWRP-LKYYKRFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,4S,5S)-3,4,5-trihydroxy-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
• IUPAC Traditional name: [(2R,3R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({hydroxy[(2R,4S,5S)-3,4,5-trihydroxy-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxan-2-yl]oxyphosphoryl}oxy)phosphinic acid
• Synonyms: Uridine 5'-(Trihydrogen Diphosphate) P'-(α-D-Glucopyranosyl-13C6) Ester Diammonium Salt; Uridine Diphosphate Glucose-13C6 Diammonium Salt; Uridine 5'-Diphospho-α-D-glucose-13C6 Diammonium Salt

Database IDs

• CAS Number: 904293-00-1
• PubChem SID: 164235309
• PubChem CID: 71752890

CALCULATED PROPERTIES

• Acid pKa: 1.7326003
• H Acceptors: 14
• H Donor: 9
• LogD (pH = 5.5): -9.414037
• LogD (pH = 7.4): -9.745448
• Log P: -4.9966083
• Molar Refractivity: 106.4558 cm^3
• Polarizability: 44.259937 Å^3
• Polar Surface Area: 291.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - U829957

A labelled phosphorylated uridine derivative used in nucleotide sugars metabolism as an activated form of glucose as a substrate for the enzyme glucosyltransferases. It is used in the treatment of chronic alcoholism. It is used in characterization of limo

REFERENCES

• Rademacher T. et al.: Annu. Rev. Biochem., 57, 785 (1988)
• Spaggiari, G. et al.: Clin. Terap., 51, 137 (1988)
• Karim, M.R. et al.: Food Chem., 76, 431 (1988)