triammonium [(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methyl (phosphonatooxy)phosphonate

• ChemBase ID: 169594
• Molecular Formular: C9H22F2N6O10P2
• Molecular Mass: 474.2495084
• Monoisotopic Mass: 474.08407063
• SMILES: [C@H]1(C([C@@H](O[C@@H]1COP(=O)(OP(=O)([O-])[O-])[O-])n1c(=O)nc(cc1)N)(F)F)O.[NH4+].[NH4+].[NH4+]
• Canonical SMILES: Nc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@@H](C1(F)F)O)COP(=O)(OP(=O)([O-])[O-])[O-].[NH4+].[NH4+].[NH4+]
• InChI: InChI=1S/C9H13F2N3O10P2.3H3N/c10-9(11)6(15)4(3-22-26(20,21)24-25(17,18)19)23-7(9)14-2-1-5(12)13-8(14)16;;;/h1-2,4,6-7,15H,3H2,(H,20,21)(H2,12,13,16)(H2,17,18,19);3*1H3/t4-,6+,7-;;;/m1.../s1
• InChIKey: DAEWGKJAIQAIEW-OWLHOBMCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triammonium [(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methyl (phosphonatooxy)phosphonate
• IUPAC Traditional name: triammonium [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methyl phosphonatooxyphosphonate
• Synonyms: 2'-Deoxy-2',2'-difluorocytidine 5'-(Trihydrogen Diphosphate) Ammonium Salt; Gemcitabine 5'-Diphosphate Ammonium Salt; Gemcitabine Diphosphate Ammonium Salt

Database IDs

• PubChem SID: 162263726
• PubChem CID: 71317052

CALCULATED PROPERTIES

• Acid pKa: 1.773211
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): -6.414953
• LogD (pH = 7.4): -7.0459375
• Log P: -2.0119042
• Molar Refractivity: 71.631 cm^3
• Polarizability: 29.687172 Å^3
• Polar Surface Area: 209.93 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G305025

Gemcitabine Diphosphate is a phosphorylated metabolite of Gemcitabine (G305000), an antineoplastic agent.

REFERENCES

• Baker, C., et al.: J. Med. Chem., 34, 1879 (1991)
• Huang, P., et al.: Cancer Res., 51, 6110 (1991)
• Plunkett, W., et al.: Nucleosides Nucleotides, 16, 1261 (1991)