CHEBI:39455 - unoprostone

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ChEBI Name unoprostone
ChEBI ID CHEBI:39455
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H38O5
Net Charge 0
Average Mass 382.53412
Monoisotopic Mass 382.27192
InChI InChI=1S/C22H38O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,18-21,24-25H,2-5,7-8,10-16H2,1H3,(H,26,27)/b9-6-/t18-,19-,20+,21-/m1/s1
InChIKey TVHAZVBUYQMHBC-SNHXEXRGSA-N
SMILES CCCCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Application(s): antiglaucoma drug
Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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ChEBI Ontology
Outgoing unoprostone (CHEBI:39455) has role antiglaucoma drug (CHEBI:39456)
unoprostone (CHEBI:39455) has role antihypertensive agent (CHEBI:35674)
unoprostone (CHEBI:39455) is a ketone (CHEBI:17087)
unoprostone (CHEBI:39455) is a oxo monocarboxylic acid (CHEBI:35871)
unoprostone (CHEBI:39455) is a prostaglandins Fα (CHEBI:36066)
Incoming isopropyl unoprostone (CHEBI:31731) has functional parent unoprostone (CHEBI:39455)
IUPAC Name
(5Z,9α,11α)-9,11-dihydroxy-15-oxo-20a,20b-dihomoprost-5-en-1-oic acid
INN Source
unoprostone ChemIDplus
Synonyms Sources
(+)-(Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)-5-heptenoic acid ChemIDplus
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoic acid IUPAC
13,14-dihydro-15-keto-20-ethyl PGF2α ChEBI
Manual Xref Database
Unoprostone Wikipedia
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Registry Numbers Types Sources
120373-36-6 CAS Registry Number ChemIDplus
9363775 Reaxys Registry Number Reaxys
9363775 Beilstein Registry Number Beilstein
Last Modified
18 July 2011