7-[(1R,2R,3R)-2-[4,4-difluoro-3-oxo(6,6,7,7,8,8,8-2H7)octyl]-3-hydroxy-5-oxocyclopentyl]heptanoic acid

• ChemBase ID: 172420
• Molecular Formular: C20H32F2O5
• Molecular Mass: 390.4618864
• Monoisotopic Mass: 390.22178056
• SMILES: [C@@H]1(CCC(=O)C(CCCC)(F)F)[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)(F)F
• InChI: InChI=1S/C20H32F2O5/c1-2-3-12-20(21,22)18(25)11-10-15-14(16(23)13-17(15)24)8-6-4-5-7-9-19(26)27/h14-15,17,24H,2-13H2,1H3,(H,26,27)/t14-,15-,17-/m1/s1
• InChIKey: DBVFKLAGQHYVGQ-BFYDXBDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(1R,2R,3R)-2-[4,4-difluoro-3-oxo(6,6,7,7,8,8,8-^2H₇)octyl]-3-hydroxy-5-oxocyclopentyl]heptanoic acid
• IUPAC Traditional name: 7-[(1R,2R,3R)-2-[4,4-difluoro-3-oxo(6,6,7,7,8,8,8-^2H₇)octyl]-3-hydroxy-5-oxocyclopentyl]heptanoic acid
• Synonyms: (11α)-16,16-Difluoro-11-hydroxy-9,15-dioxo-prostan-1-oic Acid-d7; Ru 0211-d7; Lubiprostone-d7

Database IDs

• PubChem SID: 164228330
• PubChem CID: 71749848

CALCULATED PROPERTIES

• Acid pKa: 4.30448
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.1637552
• LogD (pH = 7.4): 1.4243792
• Log P: 4.384106
• Molar Refractivity: 96.711 cm^3
• Polarizability: 37.678226 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Thick Yellow Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L473503

Labelled 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 o

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)