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CHEBI:8713 - quinapril

Default Structure
ChEBI IDCHEBI:8713
ChEBI Namequinapril
Stars
DefinitionA 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.
Last Modified1 August 2018
DownloadsMolfile
FormulaC25H30N2O5
Net Charge0
Average Mass438.524
Monoisotopic Mass438.21547
SMILESCCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1Cc2ccccc2C[C@H]1C(=O)O
InChIInChI=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
InChIKeyJSDRRTOADPPCHY-HSQYWUDLSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
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).
Applications:
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.
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).
ChEBI Ontology
Outgoing Relation(s)
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  Source
quinaprilWHO MedNet
quinaprilChemIDplus
quinaprilWHO MedNet
quinaprilumChemIDplus
Synonyms  Source
(3S)-2-{N-[(2S)-1-ethoxycarbonyl-4-phenylbutan-2-yl]-L-alanyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidIUPAC
QuinaprilKEGG COMPOUND
Manual XrefsDatabases
2340DrugCentral
C07398KEGG COMPOUND
D03752KEGG DRUG
DB00881DrugBank
LSM-3620LINCS
QuinaprilWikipedia
US4344949Patent
Registry NumbersSources
CAS:85441-61-8KEGG COMPOUND
CAS:85441-61-8ChemIDplus
Citations