7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid

• ChemBase ID: 72777
• Molecular Formular: C20H32F2O5
• Molecular Mass: 390.4618864
• Monoisotopic Mass: 390.22178056
• SMILES: C1(=O)C[C@@H]2[C@@H]([C@H]1CCCCCCC(=O)O)CC[C@@](O2)(C(F)(CCCC)F)O
• Canonical SMILES: CCCCC([C@@]1(O)CC[C@H]2[C@H](O1)CC(=O)[C@@H]2CCCCCCC(=O)O)(F)F
• InChI: InChI=1S/C20H32F2O5/c1-2-3-11-19(21,22)20(26)12-10-15-14(16(23)13-17(15)27-20)8-6-4-5-7-9-18(24)25/h14-15,17,26H,2-13H2,1H3,(H,24,25)/t14-,15-,17-,20-/m1/s1
• InChIKey: WGFOBBZOWHGYQH-MXHNKVEKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-octahydrocyclopenta[b]pyran-5-yl]heptanoic acid
• IUPAC Traditional name: @lubiprostone
• Synonyms: Amitiza; RU-0211; SPI-0211; Lubiprostone

Database IDs

• CAS Number: 136790-76-6
• PubChem SID: 162037698
• PubChem CID: 157920

CALCULATED PROPERTIES

• Acid pKa: 4.3044786
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.343517
• LogD (pH = 7.4): 1.6019012
• Log P: 4.5638967
• Molar Refractivity: 95.6009 cm^3
• Polarizability: 37.576176 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1675

Research Area: Metabolic Disease
Biological Activity:
Lubiprostone(Amitiza) is a gastrointestinal agent used for the treatment of idiopathic chronic constipation. It is a bicyclic fatty acid (more precisely, prostaglandin E1) derivative that acts by specifically activating ClC-2 chloride channels on the apical aspect of gastrointestinal epithelial cells, producing a chloride-rich fluid secretion. These secretions soften the stool, increase motility, and promote spontaneous bowel movements (SBM). [1]

REFERENCES

• http://en.wikipedia.org/wiki/Lubiprostone