benzyl N-{1-[(2R,4S,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate

• ChemBase ID: 163630
• Molecular Formular: C17H17F2N3O6
• Molecular Mass: 397.3301864
• Monoisotopic Mass: 397.10854172
• SMILES: [C@H]1(C([C@@H](O[C@@H]1CO)n1c(=O)nc(cc1)NC(=O)OCc1ccccc1)(F)F)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)(F)F)n1ccc(nc1=O)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C17H17F2N3O6/c18-17(19)13(24)11(8-23)28-14(17)22-7-6-12(20-15(22)25)21-16(26)27-9-10-4-2-1-3-5-10/h1-7,11,13-14,23-24H,8-9H2,(H,20,21,25,26)/t11-,13+,14-/m1/s1
• InChIKey: KFZMOOGZFANFGH-KWCYVHTRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-{1-[(2R,4S,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}carbamate
• IUPAC Traditional name: benzyl N-{1-[(2R,4S,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl}carbamate
• Synonyms: 2'-Deoxy-2',2'-difluoro-N-[(phenylmethoxy)carbonyl]-cytidine; [1-(2-Deoxy-2,2-difluoro-β-D-erythro-pentofuranosyl)-1,2-dihydro-2-oxo-4-pyrimidinyl]- carbamic Acid Phenylmethyl Ester; N-Carboxybenzyl Gemcitabine

Database IDs

• CAS Number: 138685-83-3
• PubChem SID: 162257765
• PubChem CID: 71314506

CALCULATED PROPERTIES

• Acid pKa: 9.40948
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.80861884
• LogD (pH = 7.4): 0.804918
• Log P: 0.8086663
• Molar Refractivity: 88.9303 cm^3
• Polarizability: 34.44527 Å^3
• Polar Surface Area: 120.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >115°C (dec.)

DETAILS

Toronto Research Chemicals - C177800

Gemcitabine (G305000) derivative.