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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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
Search Google for chemical match using the InChIKey WGFOBBZOWHGYQH-MXHNKVEKSA-N
Search Google for chemicals with the same backbone WGFOBBZOWHGYQH
Search PubMed clinical trials lubiprostone
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Search PubMed titles/abstracts lubiprostone
UniChem Compound Search for chemical match using the InChIKey WGFOBBZOWHGYQH-MXHNKVEKSA-N
UniChem Connectivity Search for chemical match using the InChIKey WGFOBBZOWHGYQH-MXHNKVEKSA-N
Wikipedia Lubiprostone