4-amino-5-fluoro-1-[5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1,2-dihydro(2-13C,1,3-15N2)pyrimidin-2-one

• ChemBase ID: 167975
• Molecular Formular: C9H10FN3O3
• Molecular Mass: 230.17187583
• Monoisotopic Mass: 230.06804404
• SMILES: C1=CC(OC1[15n]1[13c](=O)[15n]c(c(c1)F)N)CO
• Canonical SMILES: Nc1[15n][13c](=O)[15n](cc1F)C1OC(C=C1)CO
• InChI: InChI=1S/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/i9+1,12+1,13+1
• InChIKey: HSBKFSPNDWWPSL-NVYOQZELSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-5-fluoro-1-[5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1,2-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one
• IUPAC Traditional name: 4-amino-5-fluoro-1-[5-(hydroxymethyl)-2,5-dihydrofuran-2-yl](2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one
• Synonyms: 4-Amino-1-[(2S,5R)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-5-fluoro-2(1H)-pyrimidinone-13C,15N2; ACH 126443-13C,15N2; L-Fd 4C-13C,15N2; Elvucitabine-13C,15N2

Database IDs

• PubChem SID: 162262107
• PubChem CID: 71316314

CALCULATED PROPERTIES

• Acid pKa: 14.630858
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.81018883
• LogD (pH = 7.4): -0.81018883
• Log P: -0.81018883
• Molar Refractivity: 53.1413 cm^3
• Polarizability: 19.687513 Å^3
• Polar Surface Area: 88.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E515002

A novel antiviral agent.

REFERENCES

• Chou, K., et al.: J. Biol. Chem., 275, 31009 (2000)
• Gourdeau, H., et al.: Cancer Res., 61, 7217 (2000)
• Achiwa, H., et al.: Cancer Sci., 95, 753 (2000)
• Bobola, M., et al.: Clin. Cancer Res., 11, 7405 (2000)