benzyl 7-[(1R,2R,3R)-2-(4,4-difluoro-3-hydroxyoctyl)-3-hydroxy-5-oxocyclopentyl]heptanoate

• ChemBase ID: 170712
• Molecular Formular: C27H40F2O5
• Molecular Mass: 482.6003064
• Monoisotopic Mass: 482.28438082
• SMILES: C(CC(C(CCCC)(F)F)O)[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)OCc1ccccc1)O
• Canonical SMILES: CCCCC(C(CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OCc1ccccc1)O)(F)F
• InChI: InChI=1S/C27H40F2O5/c1-2-3-17-27(28,29)25(32)16-15-22-21(23(30)18-24(22)31)13-9-4-5-10-14-26(33)34-19-20-11-7-6-8-12-20/h6-8,11-12,21-22,24-25,31-32H,2-5,9-10,13-19H2,1H3/t21-,22-,24-,25?/m1/s1
• InChIKey: RPXJEOQZOUXYRP-HVIZWMAQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 7-[(1R,2R,3R)-2-(4,4-difluoro-3-hydroxyoctyl)-3-hydroxy-5-oxocyclopentyl]heptanoate
• IUPAC Traditional name: benzyl 7-[(1R,2R,3R)-2-(4,4-difluoro-3-hydroxyoctyl)-3-hydroxy-5-oxocyclopentyl]heptanoate
• Synonyms: (11α)-16,16-Difluoro-11,15-dihydroxy-9-oxoprostan Phenylmethyl Ester; 15-Hydroxy Lubiprostone Phenylmethyl Ester

Database IDs

• PubChem SID: 164226622
• PubChem CID: 71749097

CALCULATED PROPERTIES

• Acid pKa: 12.625422
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 5.6909456
• LogD (pH = 7.4): 5.6909432
• Log P: 5.6909456
• Molar Refractivity: 126.915 cm^3
• Polarizability: 49.784126 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetonitrile; Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Colorless oil

DETAILS

Toronto Research Chemicals - H943895

Protected Hydroxy Lubiprostone (H943890), a halogenated bioactive lipid.

REFERENCES

• Dalemans, W., et al.: Nature, 354, 526 (1991)
• Sakai, H., et al.: J. Biol. Chem., 270, 18781 (1991)
• Chan, L., et al.: Biology Reprod., 60, 374 (1991)