Molecular Identity
Quinapril
(3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid
PubChem CID: 54892
Quinapril is a member of the class of isoquinolines that is (3S)-2-L-alanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in which the alpha-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. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, an antihypertensive agent and a prodrug. It is a tertiary carboxamide, an ethyl ester, a member of isoquinolines and a dicarboxylic acid monoester.
2D Structure
Properties
C25H30N2O5
Molecular Formula
438.50
Molecular Weight
g/mol
438.2155
Exact Mass
Da
1.2
XLogP
Drug-like (Lipinski: < 5)
95.9
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
6
H-Bond Acceptors
648
Complexity
SMILES
Canonical SMILES
SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3=CC=CC=C3CC2C(=O)OIsomeric SMILES
SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=CC=CC=C3C[C@H]2C(=O)OSynonyms(20)
quinapril85441-61-8Quinaprilum(3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acidC09AA06RJ84Y44811CHEBI:8713DTXSID40235473-Isoquinolinecarboxylic acid, 2-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-, (3S-(2(R*(R*)),3R*))-3-Isoquinolinecarboxylic acid, 2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, (3S)-(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(3S)-2-((2S)-2-(((2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid(3S)-2-((2S)-2-(((2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-3,4-dihydro-1H-isoquinoline-3-carboxylic acid3-Isoquinolinecarboxylic acid, 2-((2S)-2-(((1S)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-, (3S)-RefChem:57154
Data from PubChem (NCBI)
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Trials and conditions connected to Quinapril
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