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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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
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Withdrawn drug?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
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