[({[(2R,3R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

• ChemBase ID: 179397
• Molecular Formular: C9H14N2O12P2
• Molecular Mass: 404.161182
• Monoisotopic Mass: 404.00219716
• SMILES: [C@H]1(C([C@@H](O[C@@H]1COP(=O)(OP(=O)(O)O)O)n1c(=O)[nH]c(=O)cc1)O)O
• Canonical SMILES: O[C@H]1[C@@H](COP(=O)(OP(=O)(O)O)O)O[C@H](C1O)n1ccc(=O)[nH]c1=O
• InChI: InChI=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
• InChIKey: XCCTYIAWTASOJW-JDNPWWSISA-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)phosphoryl)oxy]phosphonic acid
• IUPAC Traditional name: {[(2R,3R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
• Synonyms: Uridine 5'-(Trihydrogen Diphosphate) Sodium Salt; Uridine 5'-(Trihydrogen Pyrophosphate) Sodium Salt; UDP-Sodium Salt; Uridine 5'-Diphosphate Sodium Salt

Database IDs

• CAS Number: 21931-53-3
• PubChem SID: 164235307
• PubChem CID: 44298965

CALCULATED PROPERTIES

• Acid pKa: 1.7717429
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -7.3636847
• LogD (pH = 7.4): -7.99675
• Log P: -2.9606066
• Molar Refractivity: 74.3114 cm^3
• Polarizability: 30.312477 Å^3
• Polar Surface Area: 212.39 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - U829920

A phosphorylated derivative of the nucleoside Uridine. It is further phosphorylated by nucleoside diphosphokinase to form the triphosphate analogue.

REFERENCES

• Simuth, J. et al.: Biologia, 31, 683 (1976)