CHEBI:8713 - quinapril

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ChEBI Name quinapril
ChEBI ID CHEBI:8713
Definition A member of the class of isoquinolines that is (3S)-2-L-alanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in which the α-amino group of the alanyl residue has been substituted by a 1-ethoxycarbonyl-4-phenylbutan-2-yl group (the all-S isomer). A prodrug for quinaprilat (by hydrolysis of the ethyl ester to the corresponding carboxylic acid), it is used as an angiotensin-converting enzyme inhibitor (ACE inhibitor) used (generally as the hydrochloride salt) for the treatment of hypertension and congestive heart failure.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H30N2O5
Net Charge 0
Average Mass 438.517
Monoisotopic Mass 438.215
InChI InChI=1S/C25H30N2O5/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30)/t17-,21-,22-/m0/s1
InChIKey JSDRRTOADPPCHY-HSQYWUDLSA-N
SMILES C1C2=C(C[C@H](N1C([C@@H](N[C@H](C(OCC)=O)CCC=3C=CC=CC3)C)=O)C(O)=O)C=CC=C2
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): EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
Application(s): EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor
An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing quinapril (CHEBI:8713) has role antihypertensive agent (CHEBI:35674)
quinapril (CHEBI:8713) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
quinapril (CHEBI:8713) has role prodrug (CHEBI:50266)
quinapril (CHEBI:8713) is a dicarboxylic acid monoester (CHEBI:36244)
quinapril (CHEBI:8713) is a ethyl ester (CHEBI:23990)
quinapril (CHEBI:8713) is a isoquinolines (CHEBI:24922)
quinapril (CHEBI:8713) is a tertiary carboxamide (CHEBI:140326)
IUPAC Names
(3S)-2-{(2S)-2-[(1S)-1-ethoxycarbonyl-3-phenylpropylamino]propanoyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
(3S)-2-{N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
INNs Sources
quinapril ChemIDplus
quinapril WHO MedNet
quinapril WHO MedNet
quinaprilum ChemIDplus
Synonyms Sources
(3S)-2-{N-[(2S)-1-ethoxycarbonyl-4-phenylbutan-2-yl]-L-alanyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid IUPAC
Quinapril KEGG COMPOUND
Manual Xrefs Databases
2340 DrugCentral
C07398 KEGG COMPOUND
D03752 KEGG DRUG
DB00881 DrugBank
LSM-3620 LINCS
Quinapril Wikipedia
US4344949 Patent
View more database links
Registry Number Type Source
85441-61-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17404826 PubMed citation Europe PMC
27165572 PubMed citation Europe PMC
27169890 PubMed citation Europe PMC
29980144 PubMed citation Europe PMC
Last Modified
01 August 2018