(2R,3R,4R,5R)-2-(5-fluoro-2-oxo-4-{[(pentyloxy)carbonyl]amino}-1,2-dihydropyrimidin-1-yl)-4-hydroxy-5-methyloxolan-3-yl benzoate (2R,3S,4R,5R)-5-(5-fluoro-2-oxo-4-{[(pentyloxy)carbonyl]amino}-1,2-dihydropyrimidin-1-yl)-4-hydroxy-2-methyloxolan-3-yl benzoate

• ChemBase ID: 163601
• Molecular Formular: C44H52F2N6O14
• Molecular Mass: 926.9122864
• Monoisotopic Mass: 926.35095681
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1cc(c(nc1=O)NC(=O)OCCCCC)F)C)OC(=O)c1ccccc1)O.[C@H]1([C@@H]([C@H](O[C@H]1n1cc(c(nc1=O)NC(=O)OCCCCC)F)C)O)OC(=O)c1ccccc1
• Canonical SMILES: CCCCCOC(=O)Nc1nc(=O)n(cc1F)[C@@H]1O[C@@H]([C@H]([C@H]1OC(=O)c1ccccc1)O)C.CCCCCOC(=O)Nc1nc(=O)n(cc1F)[C@@H]1O[C@@H]([C@H]([C@H]1O)OC(=O)c1ccccc1)C
• InChI: InChI=1S/2C22H26FN3O7/c1-3-4-8-11-31-22(30)25-18-15(23)12-26(21(29)24-18)19-16(27)17(13(2)32-19)33-20(28)14-9-6-5-7-10-14;1-3-4-8-11-31-22(30)25-18-15(23)12-26(21(29)24-18)19-17(16(27)13(2)32-19)33-20(28)14-9-6-5-7-10-14/h2*5-7,9-10,12-13,16-17,19,27H,3-4,8,11H2,1-2H3,(H,24,25,29,30)/t2*13-,16-,17-,19-/m11/s1
• InChIKey: QBFKZIOVGLEAGU-ICNBCIPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-2-(5-fluoro-2-oxo-4-{[(pentyloxy)carbonyl]amino}-1,2-dihydropyrimidin-1-yl)-4-hydroxy-5-methyloxolan-3-yl benzoate (2R,3S,4R,5R)-5-(5-fluoro-2-oxo-4-{[(pentyloxy)carbonyl]amino}-1,2-dihydropyrimidin-1-yl)-4-hydroxy-2-methyloxolan-3-yl benzoate
• IUPAC Traditional name: (2R,3R,4R,5R)-2-(5-fluoro-2-oxo-4-{[(pentyloxy)carbonyl]amino}pyrimidin-1-yl)-4-hydroxy-5-methyloxolan-3-yl benzoate (2R,3S,4R,5R)-5-(5-fluoro-2-oxo-4-{[(pentyloxy)carbonyl]amino}pyrimidin-1-yl)-4-hydroxy-2-methyloxolan-3-yl benzoate
• Synonyms: 5’-Deoxy-5-fluoro-N-[(pentyloxy)carbonyl]cytidine Benozate; Capecitabine Benzoate (mixture of 2'(3')-benzoate isomers)

Database IDs

• PubChem SID: 162257736
• PubChem CID: 71314495

CALCULATED PROPERTIES

• Acid pKa: 8.226103
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.2626138
• LogD (pH = 7.4): 3.2102525
• Log P: 3.263336
• Molar Refractivity: 112.568 cm^3
• Polarizability: 43.893364 Å^3
• Polar Surface Area: 126.76 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: White Crystal

DETAILS

Toronto Research Chemicals - C175670

Protected Capecitabine (C175650). An antineoplastic agent. A prodrug of Doxifluridine (D556750).

REFERENCES

• Muss, H., et al.: New Eng. J. Med., 360, 2055 (2009)
• Takahashi, S., et al.: Drug Metab. Disposition, 37, 956 (2009)
• Saltz, L., et al.: J. Clin. Oncol., 27, 653 (2009)
• Sanderson, H., et al.: Toxicol. Lett., 187, 84 (2009)