lubiprostone   Click here for help

GtoPdb Ligand ID: 4242

Synonyms: Amitiza® | SPI-0211
Approved drug
lubiprostone is an approved drug (FDA (2006))
Compound class: Synthetic organic
Comment: Chemically lubiprostone is a bicyclic fatty acid derived from prostaglandin E1 (PGE1). It acts as selective activator of ClC-2 chloride channels located at the apical aspect of gastrointestinal epithelial cells.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 83.83
Molecular weight 390.22
XLogP 4.31
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCCCC(C1(O)CCC2C(O1)CC(=O)C2CCCCCCC(=O)O)(F)F
Isomeric 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
InChI Key WGFOBBZOWHGYQH-MXHNKVEKSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2006))
IUPAC Name Click here for help
7-[(2R,4aR,5R,7aR)-2-(1,1-difluoropentyl)-2-hydroxy-6-oxo-3,4,4a,5,7,7a-hexahydrocyclopenta[e]pyran-5-yl]heptanoic acid
International Nonproprietary Names Click here for help
INN number INN
8254 lubiprostone
Synonyms Click here for help
Amitiza® | SPI-0211
Database Links Click here for help
CAS Registry No. 333963-40-9 (source: Scifinder)
ChEMBL Ligand CHEMBL1201134
DrugBank Ligand DB01046
DrugCentral Ligand 4123
GtoPdb PubChem SID 178101059
PubChem CID 157920
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Wikipedia Lubiprostone