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

• ChemBase ID: 171516
• Molecular Formular: C9H11IN2O5
• Molecular Mass: 354.09851
• Monoisotopic Mass: 353.97126946
• SMILES: C1(O)[C@@H](CO)O[C@H](C1)n1c(=O)[nH]c(=O)c(c1)I
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1cc(I)c(=O)[nH]c1=O
• InChI: InChI=1S/C9H11IN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5?,6-,7-/m1/s1
• InChIKey: XQFRJNBWHJMXHO-JXBXZBNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-3H-pyrimidine-2,4-dione
• Synonyms: 1-(2-Deoxy-β-D-threo-pentofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione; 1-(2-Deoxy-β-D-threo-pentofuranosyl)-5-iodouracil; 3'-epi-Idoxuridine

Database IDs

• CAS Number: 93780-25-7
• PubChem SID: 164227426
• PubChem CID: 6419973

CALCULATED PROPERTIES

• Acid pKa: 8.056083
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.5301102
• LogD (pH = 7.4): -0.6144564
• Log P: -0.5289186
• Molar Refractivity: 64.4039 cm^3
• Polarizability: 25.542524 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I205760

The 3’-enantiomer of Idoxuridine (I205750). Antitumor nucleoside enantiomer thymidine kinase used as potential antiviral agents.

REFERENCES

• Chang, C., et al.: J. Biol. Chem., 267, 22414 (1992)
• Pressacco, J., et al.: Cancer Res., 54, 3772 (1992)