{2-[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]ethyl}trimethylazanium

• ChemBase ID: 169591
• Molecular Formular: C14H24F2N4O10P2
• Molecular Mass: 508.3054884
• Monoisotopic Mass: 508.09357269
• SMILES: [C@H]1(C([C@@H](O[C@@H]1COP(=O)(OP(=O)(OCC[N+](C)(C)C)[O-])O)n1c(=O)nc(cc1)N)(F)F)O
• Canonical SMILES: O[C@H]1[C@@H](COP(=O)(OP(=O)(OCC[N+](C)(C)C)[O-])O)O[C@H](C1(F)F)n1ccc(nc1=O)N
• InChI: InChI=1S/C14H24F2N4O10P2/c1-20(2,3)6-7-27-31(23,24)30-32(25,26)28-8-9-11(21)14(15,16)12(29-9)19-5-4-10(17)18-13(19)22/h4-5,9,11-12,21H,6-8H2,1-3H3,(H3-,17,18,22,23,24,25,26)/t9-,11+,12-/m1/s1
• InChIKey: WEAJNZCNBIEIHD-ADEWGFFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]ethyl}trimethylazanium
• IUPAC Traditional name: [2-({[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)ethyl]trimethylazanium
• Synonyms: Gemcitabine 5’-Diphosphate Choline; Gemcitabine Diphosphate Choline

Database IDs

• PubChem SID: 162263723
• PubChem CID: 71317047

CALCULATED PROPERTIES

• Acid pKa: 1.8451427
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -5.759049
• LogD (pH = 7.4): -6.123097
• Log P: -5.7776356
• Molar Refractivity: 112.2894 cm^3
• Polarizability: 40.476093 Å^3
• Polar Surface Area: 193.27 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 224-226°C

Safety Information

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

DETAILS

Toronto Research Chemicals - G305015

Gemcitabine (G305000) derivative. An antineoplastic agent.

REFERENCES

• Kennedy., E.P., et al.: J. Biol. Chem., 222, 193 (1956)