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

• ChemBase ID: 171868
• Molecular Formular: C12H18N2O5
• Molecular Mass: 270.28172
• Monoisotopic Mass: 270.12157169
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)n1c(=O)[nH]c(=O)c(c1)C(C)C)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cc(C(C)C)c(=O)[nH]c1=O
• InChI: InChI=1S/C12H18N2O5/c1-6(2)7-4-14(12(18)13-11(7)17)10-3-8(16)9(5-15)19-10/h4,6,8-10,15-16H,3,5H2,1-2H3,(H,13,17,18)/t8-,9-,10-/m1/s1
• InChIKey: PHUUXVYXSRZACJ-OPRDCNLKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(propan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-isopropyl-3H-pyrimidine-2,4-dione
• Synonyms: 2'-Deoxy-5-(1-methylethyl)uridine; 2'-Deoxy-5-isopropyluridine; 5-Isopropyldeoxyuridine; Epervudine; 5-Isopropyl-2'-deoxyuridine

Database IDs

• CAS Number: 60136-25-6
• PubChem SID: 164227778
• PubChem CID: 71749595

CALCULATED PROPERTIES

• Acid pKa: 9.94625
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.38748118
• LogD (pH = 7.4): -0.38868463
• Log P: -0.38746583
• Molar Refractivity: 64.5616 cm^3
• Polarizability: 25.633968 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I824410

5-Isopropyl-2'-deoxyuridine (IP5dU) was recently recognized as a clinical useful antiherpetic (HSV-1) agent.

REFERENCES

• Levin, R., et al.: Cancer, 72, 2895 (1993)
• Cook, G., et al.: Chem. Biol., 6, 451 (1993)