4-amino-1-[(2R,4S,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro(2,5,6-13C3,1,3-15N2)pyrimidin-2-one hydrochloride

• ChemBase ID: 169589
• Molecular Formular: C9H12ClF2N3O4
• Molecular Mass: 304.62386871
• Monoisotopic Mass: 304.0525743
• SMILES: Cl.[C@H]1(C([C@@H](O[C@@H]1CO)[15n]1[13c](=O)[15n]c([13cH][13cH]1)N)(F)F)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)(F)F)[15n]1[13cH][13cH]c([15n][13c]1=O)N.Cl
• InChI: InChI=1S/C9H11F2N3O4.ClH/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17;/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17);1H/t4-,6+,7-;/m1./s1/i1+1,2+1,8+1,13+1,14+1
• InChIKey: OKKDEIYWILRZIA-GTSUYYBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4S,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro(2,5,6-^1^3C₃,1,3-^1^5N₂)pyrimidin-2-one hydrochloride
• IUPAC Traditional name: 4-amino-1-[(2R,4S,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](2,5,6-^1^3C₃,1,3-^1^5N₂)pyrimidin-2-one hydrochloride
• Synonyms: 2’-Deoxy-2’,2’-difluorocytidine-13C,15N2 Hydrochloride; Gemcitabine-13C3,15N2 Hydrochloride

Database IDs

• PubChem SID: 162263721
• PubChem CID: 71317044

CALCULATED PROPERTIES

• Acid pKa: 11.51707
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.4665402
• LogD (pH = 7.4): -1.4665728
• Log P: -1.4665396
• Molar Refractivity: 53.2503 cm^3
• Polarizability: 20.563793 Å^3
• Polar Surface Area: 108.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G305003

Labelled Gemcitabine, an antineoplastic.

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)