CHEBI:135633 - beraprost

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ChEBI Name beraprost
ChEBI ID CHEBI:135633
Definition An organic heterotricyclic compound that is (3aS,8bS)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan in which the hydrogens at positions 1R, 2R and 5 are replaced by (3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl, hydroxy and 3-carboxypropyl groups, respectively. It is a prostaglandin receptor agonist which is approved to treat pulmonary arterial hypertension in Asia.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H30O5
Net Charge 0
Average Mass 398.499
Monoisotopic Mass 398.20932
InChI InChI=1S/C24H30O5/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28)/b13-12+/t15?,17-,19+,20+,21-,23-/m0/s1
InChIKey CTPOHARTNNSRSR-APJZLKAGSA-N
SMILES [H][C@]12C[C@@H](O)[C@]([H])(\C=C\[C@@H](O)C(C)CC#CC)[C@@]1([H])C1=C(O2)C(CCCC(O)=O)=CC=C1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): prostaglandin receptor agonist
An agonist that binds to and activates prostaglandin receptors.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
vasodilator agent
A drug used to cause dilation of the blood vessels.
platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
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 beraprost (CHEBI:135633) has role anti-inflammatory agent (CHEBI:67079)
beraprost (CHEBI:135633) has role antihypertensive agent (CHEBI:35674)
beraprost (CHEBI:135633) has role platelet aggregation inhibitor (CHEBI:50427)
beraprost (CHEBI:135633) has role prostaglandin receptor agonist (CHEBI:66900)
beraprost (CHEBI:135633) has role vasodilator agent (CHEBI:35620)
beraprost (CHEBI:135633) is a enyne (CHEBI:59831)
beraprost (CHEBI:135633) is a monocarboxylic acid (CHEBI:25384)
beraprost (CHEBI:135633) is a organic heterotricyclic compound (CHEBI:26979)
beraprost (CHEBI:135633) is a secondary alcohol (CHEBI:35681)
beraprost (CHEBI:135633) is a secondary allylic alcohol (CHEBI:134396)
beraprost (CHEBI:135633) is conjugate acid of beraprost(1−) (CHEBI:156557)
Incoming beraprost(1−) (CHEBI:156557) is conjugate base of beraprost (CHEBI:135633)
IUPAC Name
4-{(1R,2R,3aS,8bS)-2-hydroxy-1-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-5-yl}butanoic acid
INNs Sources
béraprost WHO MedNet
beraprost WHO MedNet
beraprost WHO MedNet
beraprostum WHO MedNet
Synonyms Sources
MDL 201229 ChemIDplus
MDL-201229 ChemIDplus
MDL201229 ChEBI
ML 1229 ChemIDplus
ML-1229 ChemIDplus
ML1229 ChEBI
Manual Xrefs Databases
343 DrugCentral
5293169 ChemSpider
Beraprost Wikipedia
D02720 KEGG DRUG
DB05229 DrugBank
View more database links
Registry Number Type Source
88430-50-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
08 March 2021