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

• ChemBase ID: 170551
• Molecular Formular: C11H16N2O6
• Molecular Mass: 272.25454
• Monoisotopic Mass: 272.10083624
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c(=O)[nH]c(=O)c(c1)CCO)O
• Canonical SMILES: OCCc1cn([C@@H]2O[C@@H]([C@@H](C2)O)CO)c(=O)[nH]c1=O
• InChI: InChI=1S/C11H16N2O6/c14-2-1-6-4-13(11(18)12-10(6)17)9-3-7(16)8(5-15)19-9/h4,7-9,14-16H,1-3,5H2,(H,12,17,18)/t7-,8-,9-/m1/s1
• InChIKey: SORQWSCHVYGEPE-IWSPIJDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-hydroxyethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-hydroxyethyl)-3H-pyrimidine-2,4-dione
• Synonyms: 2'-Deoxy-5-(2-hydroxyethyl)uridine; 5-(2-Hydroxyethyl)-2'-deoxyuridine

Database IDs

• CAS Number: 90301-60-3
• PubChem SID: 164226461
• PubChem CID: 71749030

CALCULATED PROPERTIES

• Acid pKa: 9.648249
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.1111941
• LogD (pH = 7.4): -2.1135807
• Log P: -2.1111636
• Molar Refractivity: 61.9417 cm^3
• Polarizability: 24.512402 Å^3
• Polar Surface Area: 119.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942060

A novel type of potent antiviral nucleoside analog.

REFERENCES

• Griengl, H., et al.: J. Med. Chem., 28, 1679 (1985)