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

• ChemBase ID: 177098
• Molecular Formular: C9H15N2O15P3
• Molecular Mass: 484.141083
• Monoisotopic Mass: 483.96852768
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1COP(=O)(OP(=O)(O)OP(=O)(O)O)O)c1c[nH]c(=O)[nH]c1=O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)O)O)O)O[C@H]([C@@H]1O)c1c[nH]c(=O)[nH]c1=O
• InChI: InChI=1S/C9H15N2O15P3/c12-5-4(2-23-28(19,20)26-29(21,22)25-27(16,17)18)24-7(6(5)13)3-1-10-9(15)11-8(3)14/h1,4-7,12-13H,2H2,(H,19,20)(H,21,22)(H2,16,17,18)(H2,10,11,14,15)/t4-,5-,6-,7+/m1/s1
• InChIKey: VEWJOCYCKIZKKV-GBNDHIKLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3S,4R,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC Traditional name: ({[(2R,3S,4R,5S)-5-(2,4-dioxo-1,3-dihydropyrimidin-5-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
• Synonyms: 5-[5-O-[Hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-β-D-ribofuranosyl]-2,4(1H,3H)pyrimidinedione; 5-β-D-Ribofuranosyluracil 5'-Triphosphate; Pseudouridine Triphosphate; Pseudouridine 5'-Triphosphate, >85%

Database IDs

• CAS Number: 1175-34-4
• PubChem SID: 164233008
• PubChem CID: 20762852

CALCULATED PROPERTIES

• Acid pKa: 0.8952796
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -10.744126
• LogD (pH = 7.4): -11.480615
• Log P: -4.067311
• Molar Refractivity: 85.0597 cm^3
• Polarizability: 35.133476 Å^3
• Polar Surface Area: 267.71 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P839610

Uridine analog as ribonucleate nucleotidyltransferase substrate.

REFERENCES

• Ginsberg, T., et al.: J. Biol. Chem., 243, 6300 ( (1968)
• Slapikoff, S., et al.: Biochemistry, 6, 3654 (1968)