(2R,3R,5S)-5-[4-amino-2-oxo-1,2-dihydro(2-13C,1,3-15N2)pyrimidin-1-yl]-2-[(benzoyloxy)methyl]-4,4-difluorooxolan-3-yl benzoate

• ChemBase ID: 168050
• Molecular Formular: C23H19F2N3O6
• Molecular Mass: 474.38973903
• Monoisotopic Mass: 474.12161641
• SMILES: [C@@H]1(C([C@H](O[C@@H]1COC(=O)c1ccccc1)[15n]1[13c](=O)[15n]c(cc1)N)(F)F)OC(=O)c1ccccc1
• Canonical SMILES: Nc1cc[15n]([13c](=O)[15n]1)[C@H]1O[C@@H]([C@H](C1(F)F)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• InChI: InChI=1S/C23H19F2N3O6/c24-23(25)18(34-20(30)15-9-5-2-6-10-15)16(13-32-19(29)14-7-3-1-4-8-14)33-21(23)28-12-11-17(26)27-22(28)31/h1-12,16,18,21H,13H2,(H2,26,27,31)/t16-,18-,21+/m1/s1/i22+1,27+1,28+1
• InChIKey: ZPUUYUUQQGBHBU-MEXQSHOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5S)-5-[4-amino-2-oxo-1,2-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-2-[(benzoyloxy)methyl]-4,4-difluorooxolan-3-yl benzoate
• IUPAC Traditional name: (2R,3R,5S)-5-[4-amino-2-oxo(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-2-[(benzoyloxy)methyl]-4,4-difluorooxolan-3-yl benzoate
• Synonyms: 4-Amino-1-3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone-13C,15N2; 1'-Epi Gemcitabine-13C,15N2 3',5'-Dibenzoate

Database IDs

• PubChem SID: 162262182
• PubChem CID: 71316356

CALCULATED PROPERTIES

• Acid pKa: 17.94884
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.52406
• LogD (pH = 7.4): 3.52406
• Log P: 3.52406
• Molar Refractivity: 112.8943 cm^3
• Polarizability: 43.351196 Å^3
• Polar Surface Area: 120.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 138-140°C

Safety Information

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

DETAILS

Toronto Research Chemicals - E588507

A labelled (α-anomer) intermediate of Gemcitabine; antitumor compound.

REFERENCES

• Hertel, L.W., et al.: Cancer Res., 50, 4417 (1990)
• Abbruzzese, J.L., et al.: J. Clin. Oncol., 9, 491 (1990)
• Ruiz, V.W.T., et al.: Biochem. Pharmacol., 46, 762 (1990)