({[({[(2R,3R,5R)-5-[4-amino-2-oxo-1,2-dihydro(2-13C,1,3-15N2)pyrimidin-1-yl]-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid; triethylamine

• ChemBase ID: 169593
• Molecular Formular: C15H29F2N4O13P3
• Molecular Mass: 607.30732203
• Monoisotopic Mass: 607.08862796
• SMILES: N(CC)(CC)CC.[C@@H]1(C([C@@H](O[C@@H]1COP(=O)(OP(=O)(OP(=O)(O)O)O)O)[15n]1[13c](=O)[15n]c(cc1)N)(F)F)O
• Canonical SMILES: Nc1cc[15n]([13c](=O)[15n]1)[C@@H]1O[C@@H]([C@H](C1(F)F)O)COP(=O)(OP(=O)(OP(=O)(O)O)O)O.CCN(CC)CC
• InChI: InChI=1S/C9H14F2N3O13P3.C6H15N/c10-9(11)6(15)4(25-7(9)14-2-1-5(12)13-8(14)16)3-24-29(20,21)27-30(22,23)26-28(17,18)19;1-4-7(5-2)6-3/h1-2,4,6-7,15H,3H2,(H,20,21)(H,22,23)(H2,12,13,16)(H2,17,18,19);4-6H2,1-3H3/t4-,6-,7-;/m1./s1/i8+1,13+1,14+1
• InChIKey: GYGIKKXGYQCANX-ACCKZTSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3R,5R)-5-[4-amino-2-oxo-1,2-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid; triethylamine
• IUPAC Traditional name: ({[(2R,3R,5R)-5-[4-amino-2-oxo(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid; triethylamine
• Synonyms: 2'-Deoxy-2',2'-difluorocytidine 5'-(Tetrahydrogen Triphosphate)-13C,15N2 Di(N,N-diethylethanamine); Gemcitabine Triphosphate-13C,15N2 Ditriethylamine

Database IDs

• PubChem SID: 162263725
• PubChem CID: 71317050

CALCULATED PROPERTIES

• Acid pKa: 0.9063939
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -9.11048
• LogD (pH = 7.4): -9.844007
• Log P: -2.5664964
• Molar Refractivity: 85.869 cm^3
• Polarizability: 34.88645 Å^3
• Polar Surface Area: 247.97 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G305022

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

REFERENCES

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