1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidine-2,4-dione

• ChemBase ID: 167405
• Molecular Formular: C9H10F2N2O5
• Molecular Mass: 267.16237903
• Monoisotopic Mass: 267.05320249
• SMILES: C1(C([C@H](O[C@H]1[15n]1[13c](=O)[15nH]c(=O)cc1)CO)O)(F)F
• Canonical SMILES: OC[C@H]1O[C@H](C(C1O)(F)F)[15n]1ccc(=O)[15nH][13c]1=O
• InChI: InChI=1S/C9H10F2N2O5/c10-9(11)6(16)4(3-14)18-7(9)13-2-1-5(15)12-8(13)17/h1-2,4,6-7,14,16H,3H2,(H,12,15,17)/t4-,6?,7-/m1/s1/i8+1,12+1,13+1
• InChIKey: FIRDBEQIJQERSE-CNLDSFCYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](2-^1^3C,1,3-^1^5N₂)-3H-pyrimidine-2,4-dione
• Synonyms: 2’-Deoxy-2’,2’-difluorouridine-13C,15N2; 2',2'-Difluorodeoxyuridine-13C,15N2; 2',2'-Difluoro-2'-deoxyuridine-13C,15N2

Database IDs

• PubChem SID: 162261538
• PubChem CID: 71316071

CALCULATED PROPERTIES

• Acid pKa: 9.194057
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.0843513
• LogD (pH = 7.4): -1.0911082
• Log P: -1.0842645
• Molar Refractivity: 51.2711 cm^3
• Polarizability: 20.00766 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 132-139°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D445742

An isotopically Labelled metabolite of Gemcitabine.

REFERENCES

• Wiley, J., et al.: J. Clin. Invest., 69, 479 (1982)
• Gandhi, V., et al.: Cancer Res., 50, 3675 (1982)
• Abbruzzese, J., et al.: J. Clin. Oncol., 9, 491 (1982)
• Flanagan, S., et al.: J. Biol. Chem., 272, 18026 (1982)