unoprostone isopropyl   Click here for help

GtoPdb Ligand ID: 8282

Synonyms: Rescula® (proposed trade name) | UF 021 | UF-021
Approved drug
unoprostone isopropyl is an approved drug (FDA (2000))
Compound class: Synthetic organic
Comment: Note that the INN for this compound is for the carboxylic acid, whereas the compound used clinically is the isopropyl ester.
Unoprostone was originally developed as an intraocular pressure-reducing agent for use in glaucoma, however use for this indication has been discontinued. The focus is now on unoprostone's ability to treat retinal disease [3,5].
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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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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 17
Topological polar surface area 83.83
Molecular weight 424.32
XLogP 5.39
No. Lipinski's rules broken 2

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 CCCCCCCC(=O)CCC1C(O)CC(C1CC=CCCCC(=O)OC(C)C)O
Isomeric SMILES CCCCCCCC(=O)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)OC(C)C)O
InChI InChI=1S/C25H44O5/c1-4-5-6-7-10-13-20(26)16-17-22-21(23(27)18-24(22)28)14-11-8-9-12-15-25(29)30-19(2)3/h8,11,19,21-24,27-28H,4-7,9-10,12-18H2,1-3H3/b11-8-/t21-,22-,23+,24-/m1/s1
InChI Key XXUPXHKCPIKWLR-JHUOEJJVSA-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 (2000))
Approved drug? Yes. FDA (2000)
Withdrawn drug? Yes
IUPAC Name Click here for help
propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoate
International Nonproprietary Names Click here for help
INN number INN
6920 unoprostone
Synonyms Click here for help
Rescula® (proposed trade name) | UF 021 | UF-021
Database Links Click here for help
CAS Registry No. 120373-24-2 (source: Scifinder)
ChEBI CHEBI:31731
ChEMBL Ligand CHEMBL1200661
DrugCentral Ligand 2794
GtoPdb PubChem SID 252166494
PubChem CID 5282175
Search Google for chemical match using the InChIKey XXUPXHKCPIKWLR-JHUOEJJVSA-N
Search Google for chemicals with the same backbone XXUPXHKCPIKWLR
Search PubMed clinical trials unoprostone
Search PubMed titles unoprostone
Search PubMed titles/abstracts unoprostone
UniChem Compound Search for chemical match using the InChIKey XXUPXHKCPIKWLR-JHUOEJJVSA-N
UniChem Connectivity Search for chemical match using the InChIKey XXUPXHKCPIKWLR-JHUOEJJVSA-N

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MedChemExpress
Isopropyl unoprostone (links to external site)
Cat. No. HY-109545