7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-(oxan-2-yloxy)-5-oxocyclopentyl]heptanoic acid

• ChemBase ID: 178406
• Molecular Formular: C25H40F2O6
• Molecular Mass: 474.5783064
• Monoisotopic Mass: 474.27929544
• SMILES: [C@@H]1(CCC(=O)C(CCCC)(F)F)[C@H](C(=O)C[C@H]1OC1OCCCC1)CCCCCCC(=O)O
• Canonical SMILES: CCCCC(C(=O)CC[C@H]1[C@H](OC2CCCCO2)CC(=O)[C@@H]1CCCCCCC(=O)O)(F)F
• InChI: InChI=1S/C25H40F2O6/c1-2-3-15-25(26,27)22(29)14-13-19-18(10-6-4-5-7-11-23(30)31)20(28)17-21(19)33-24-12-8-9-16-32-24/h18-19,21,24H,2-17H2,1H3,(H,30,31)/t18-,19-,21-,24?/m1/s1
• InChIKey: KPXLSWFJVXGWOV-ZFIPPKMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-(oxan-2-yloxy)-5-oxocyclopentyl]heptanoic acid
• IUPAC Traditional name: 7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-(oxan-2-yloxy)-5-oxocyclopentyl]heptanoic acid
• Synonyms: (11α)-16,16-Difluoro-9,15-dioxo-11-[(tetrahydro-2H-pyran-2-yl)oxy]prostan-1-oic Acid; O-Tetrahydropyranyl Lubiprostone

Database IDs

• CAS Number: 876068-08-5
• PubChem SID: 164234316
• PubChem CID: 58601719

CALCULATED PROPERTIES

• Acid pKa: 4.30448
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 4.707449
• LogD (pH = 7.4): 2.968073
• Log P: 5.9278
• Molar Refractivity: 119.4957 cm^3
• Polarizability: 46.901814 Å^3
• Polar Surface Area: 89.9 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T295380

Protected precursor to Lubiprostone.