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

• ChemBase ID: 179398
• Molecular Formular: C14H25N3O12P2
• Molecular Mass: 489.308722
• Monoisotopic Mass: 489.09134652
• SMILES: [C@H]1(C([C@@H](O[C@@H]1COP(=O)(OP(=O)(OCC[N+](C)(C)C)[O-])O)n1c(=O)[nH]c(=O)cc1)O)O
• Canonical SMILES: O[C@H]1[C@@H](COP(=O)(OP(=O)(OCC[N+](C)(C)C)[O-])O)O[C@H](C1O)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C14H25N3O12P2/c1-17(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)16-5-4-10(18)15-14(16)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H2-,15,18,21,22,23,24,25)/t9-,11+,12?,13-/m1/s1
• InChIKey: HLGXKBPFICLHPF-YJHHQHARSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[({[(2R,3R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]ethyl}trimethylazanium
• IUPAC Traditional name: [2-({[(2R,3R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)ethyl]trimethylazanium
• Synonyms: Uridine 5'-(Trihydrogen Diphosphate) P'-[2-(Trimethylammonio)ethyl] Ester Ammonium Salt; Uridine Diphosphate Choline Ammonium Salt

Database IDs

• CAS Number: 99492-83-8
• PubChem SID: 164235308
• PubChem CID: 71752888

CALCULATED PROPERTIES

• Acid pKa: 1.843904
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -6.707776
• LogD (pH = 7.4): -7.073909
• Log P: -6.726338
• Molar Refractivity: 111.6047 cm^3
• Polarizability: 40.80974 Å^3
• Polar Surface Area: 204.22 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - U829930

CDPcholine cholinephosphotransferase analog.

REFERENCES

• Kennedy, E.P., et al.: J. Biol. Chem., 222, 185 (1956)