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

• ChemBase ID: 167404
• Molecular Formular: C9H10F2N2O5
• Molecular Mass: 264.1829064
• Monoisotopic Mass: 264.05577787
• SMILES: C1(C([C@H](O[C@H]1n1c(=O)[nH]c(=O)cc1)CO)O)(F)F
• Canonical SMILES: OC[C@H]1O[C@H](C(C1O)(F)F)n1ccc(=O)[nH]c1=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
• InChIKey: FIRDBEQIJQERSE-ZJXFTUPMSA-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-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 2’-Deoxy-2’,2’-difluorouridine; 2',2'-Difluorodeoxyuridine; 2',2'-Difluoro-2'-deoxyuridine

Database IDs

• CAS Number: 114248-23-6
• PubChem SID: 162261537
• PubChem CID: 67279059

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: White to Off-White Solid
• Melting Point: 147-149°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D445740

A metabolite of Gemcitabine (G305000) in human plasma.

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)