8-[(1R,2R,5R)-2-(2-carboxyethyl)-5-hydroxy-3-oxocyclopentyl]-5,5-difluoro-6-hydroxyoctanoic acid

• ChemBase ID: 167819
• Molecular Formular: C16H24F2O7
• Molecular Mass: 366.3543664
• Monoisotopic Mass: 366.14900955
• SMILES: [C@@H]1(CCC(C(CCCC(=O)O)(F)F)O)[C@H](C(=O)C[C@H]1O)CCC(=O)O
• Canonical SMILES: OC(=O)CCCC(C(CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCC(=O)O)O)(F)F
• InChI: InChI=1S/C16H24F2O7/c17-16(18,7-1-2-14(22)23)13(21)5-3-9-10(4-6-15(24)25)12(20)8-11(9)19/h9-11,13,19,21H,1-8H2,(H,22,23)(H,24,25)/t9-,10-,11-,13?/m1/s1
• InChIKey: UNGXSHHHKITVHD-RUPPFBPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[(1R,2R,5R)-2-(2-carboxyethyl)-5-hydroxy-3-oxocyclopentyl]-5,5-difluoro-6-hydroxyoctanoic acid
• IUPAC Traditional name: 8-[(1R,2R,5R)-2-(2-carboxyethyl)-5-hydroxy-3-oxocyclopentyl]-5,5-difluoro-6-hydroxyoctanoic acid
• Synonyms: (7α,11)-Dihydroxy-5-keto-12,12-difluorotetranorprosta-1,16-dioic Acid

Database IDs

• PubChem SID: 162261952
• PubChem CID: 71316243

CALCULATED PROPERTIES

• Acid pKa: 4.103726
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.5322859
• LogD (pH = 7.4): -5.0465536
• Log P: 0.7220622
• Molar Refractivity: 80.7947 cm^3
• Polarizability: 31.662779 Å^3
• Polar Surface Area: 132.13 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D452835

A metabolite of Lubiprostone (L473500).