7-[(1R,2R,3R)-2-(4,4-dimethyl-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl]heptanoic acid

• ChemBase ID: 172419
• Molecular Formular: C22H38O5
• Molecular Mass: 382.53412
• Monoisotopic Mass: 382.27192432
• SMILES: [C@@H]1(CCC(=O)C(CCCC)(C)C)[C@H](C(=O)C[C@H]1O)CCCCCCC(=O)O
• Canonical SMILES: CCCCC(C(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O)(C)C
• InChI: InChI=1S/C22H38O5/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h16-17,19,24H,4-15H2,1-3H3,(H,26,27)/t16-,17-,19-/m1/s1
• InChIKey: BODKCFIJDQGFGS-ZHALLVOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R)-2-(4,4-dimethyl-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl]heptanoic acid
• IUPAC Traditional name: 7-[(1R,2R,3R)-2-(4,4-dimethyl-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl]heptanoic acid
• Synonyms: (11α)-16,16-Difluoro-11-hydroxy-9,15-dioxo-prostan-1-oic Acid; Ru 0211; Lubiprostone

Database IDs

• CAS Number: 136790-76-6
• PubChem SID: 164228329
• PubChem CID: 29982788

CALCULATED PROPERTIES

• Acid pKa: 4.30448
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.8793564
• LogD (pH = 7.4): 2.1399803
• Log P: 5.0997076
• Molar Refractivity: 105.4033 cm^3
• Polarizability: 41.80805 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 56-59°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L473500

Lubiprostone is a bicyclic fatty acid metabolite analog of Prostaglandin E1. It activates specific chloride channels in the gastrointestinal tract to stimulate intestinal fluid secretion, increase gastrointestinal transit, and improve symptoms of constip

REFERENCES

• Farthing, M., et al.: Drugs, 56, 11 (1998)
• Pare, P., et al.: Am. J. Gastroenterol., 96, 3130 (1998)
• Sloots, C., et al.: Aliment. Pharmacol. Ther., 16, 759 (1998)
• Coremans, G., et al.: Digestion, 67, 82 (1998)