1-[(3aS,4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-5-fluoro-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidine-2,4-dione

• ChemBase ID: 171892
• Molecular Formular: C12H15FN2O6
• Molecular Mass: 305.23517583
• Monoisotopic Mass: 305.08883905
• SMILES: [C@H]12C([C@H](O[C@H]1[15n]1cc(c(=O)[15nH][13c]1=O)F)CO)OC(O2)(C)C
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]2C1OC(O2)(C)C)[15n]1cc(F)c(=O)[15nH][13c]1=O
• InChI: InChI=1S/C12H15FN2O6/c1-12(2)20-7-6(4-16)19-10(8(7)21-12)15-3-5(13)9(17)14-11(15)18/h3,6-8,10,16H,4H2,1-2H3,(H,14,17,18)/t6-,7?,8+,10-/m1/s1/i11+1,14+1,15+1
• InChIKey: LHTMLCXJMYPWGR-HETYSVAVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3aS,4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-5-fluoro-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(3aS,4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-fluoro(2-^1^3C,1,3-^1^5N₂)-3H-pyrimidine-2,4-dione
• Synonyms: 2',3'-O-Isopropylidene-5-fluorouridine-13C,15N2; 5-Fluoro-2',3'-O-(1-methylethylidene)uridine-13C,15N2; 5-Fluoro-2',3'-O-isopropylideneuridine-13C,15N2; 5-Fluoro-2',3'-isopropylideneuridine-13C,15N2

Database IDs

• PubChem SID: 164227802
• PubChem CID: 71749604

CALCULATED PROPERTIES

• Acid pKa: 7.674201
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.5162397
• LogD (pH = 7.4): -0.69596815
• Log P: -0.5133746
• Molar Refractivity: 64.9755 cm^3
• Polarizability: 25.629929 Å^3
• Polar Surface Area: 97.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMF; DMSO; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - I825102

Suppressed in vitro primary antibody response toward sheep red blood cells (SRBC).

REFERENCES

• Kijima, I., et al.: Chem. Pharm. Bull., 30, 3278 (1982).