5-[(2S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 177097
• Molecular Formular: C9H12N2O6
• Molecular Mass: 244.20138
• Monoisotopic Mass: 244.06953611
• SMILES: [C@H]1(C([C@@H](O[C@@H]1CO)c1c[nH]c(=O)[nH]c1=O)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)c1c[nH]c(=O)[nH]c1=O
• InChI: InChI=1S/C9H12N2O6/c12-2-4-5(13)6(14)7(17-4)3-1-10-9(16)11-8(3)15/h1,4-7,12-14H,2H2,(H2,10,11,15,16)/t4-,5+,6?,7+/m1/s1
• InChIKey: PTJWIQPHWPFNBW-SRFQBUKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 5-[(2S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-dihydropyrimidine-2,4-dione
• Synonyms: 5-β-D-Ribofuranosyl-2,4(1H,3H)-Pyrimidinedione; 5-(β-D-Ribofuranosyl)uracil; 5-Ribosyluracil; NSC 162405; Pseudouridine C; β-D-Pseudouridine; Pseudouridine; ψ-Uridine; β-Pseudouridine

Database IDs

• CAS Number: 1445-07-4
• PubChem SID: 164233007
• PubChem CID: 57693399

CALCULATED PROPERTIES

• Acid pKa: 9.549382
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.100186
• LogD (pH = 7.4): -3.103181
• Log P: -3.100148
• Molar Refractivity: 52.441 cm^3
• Polarizability: 20.901344 Å^3
• Polar Surface Area: 128.12 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P839605

An isomer of the nucleoside uridine found in all species and in many classes of RNA except mRNA. It is formed by enzymes called Ψ synthases, which post-transcriptionally isomerize specific uridine residues in RNA in a process termed pseudouridylation. Stu

REFERENCES

• Ferré-D'Amaré A.R. et al.: Curr. Opin. Struct. Biol., 13, 49 (2003)
• Hamma, T. et al.: Chem. Biol., 13, 1125 (2003)
• Liang, X.H. et al.: RNA, 8, 237 (2003)
• Monobe, M. et al.: Mut. Res. Gen. Toxicol. Env. Mutagen., 538, 93 (2003)