[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methyl acetate

• ChemBase ID: 159279
• Molecular Formular: C11H13F2N3O5
• Molecular Mass: 305.2348264
• Monoisotopic Mass: 305.08232697
• SMILES: [C@@H]1(C([C@@H](O[C@@H]1COC(=O)C)n1c(=O)nc(cc1)N)(F)F)O
• Canonical SMILES: CC(=O)OC[C@H]1O[C@H](C([C@@H]1O)(F)F)n1ccc(nc1=O)N
• InChI: InChI=1S/C11H13F2N3O5/c1-5(17)20-4-6-8(18)11(12,13)9(21-6)16-3-2-7(14)15-10(16)19/h2-3,6,8-9,18H,4H2,1H3,(H2,14,15,19)/t6-,8-,9-/m1/s1
• InChIKey: HHTBRILJAHUJTL-FTLITQJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methyl acetate
• Synonyms: ((2R,3R,5R)-5-(4-Amino-2-oxopyrimidin 1(2H)-yl)-4,4-difluoro-3-hydroxy-tetrahydrofuran-2-yl)methyl Acetate; 5-O-Acetyl Gemcitabine

Database IDs

• PubChem SID: 162253414
• PubChem CID: 71312891

CALCULATED PROPERTIES

• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 11.51583
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.0254148
• LogD (pH = 7.4): -1.0254475
• Log P: -1.0254142
• Molar Refractivity: 62.4018 cm^3
• Polarizability: 24.404205 Å^3
• Polar Surface Area: 114.45 Å^2

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 180-183°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A177500

Gemcitabine (G305000) related compound.