CHEBI:4784 - enalapril

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name enalapril
ChEBI ID CHEBI:4784
Definition A dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen α to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:116847
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C20H28N2O5
Net Charge 0
Average Mass 376.44670
Monoisotopic Mass 376.200
InChI InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1
InChIKey GBXSMTUPTTWBMN-XIRDDKMYSA-N
SMILES CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O
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): 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.
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).
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 enalapril (CHEBI:4784) has functional parent enalaprilat (anhydrous) (CHEBI:4786)
enalapril (CHEBI:4784) has role antihypertensive agent (CHEBI:35674)
enalapril (CHEBI:4784) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
enalapril (CHEBI:4784) has role prodrug (CHEBI:50266)
enalapril (CHEBI:4784) is a dicarboxylic acid monoester (CHEBI:36244)
enalapril (CHEBI:4784) is a dipeptide (CHEBI:46761)
Incoming enalapril maleate (CHEBI:4785) has part enalapril (CHEBI:4784)
IUPAC Name
N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-L-proline
INNs Sources
ánalapril WHO MedNet
enalapril ChemIDplus
enalaprila ChemIDplus
enalaprilum ChemIDplus
Synonyms Sources
(S)-1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline ChemIDplus
(S)-1-{(S)-2-[1-((S)-Ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid ChEMBL
1-(N-((S)-1-carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester ChemIDplus
ENALAPRIL ChEMBL
Enalapril KEGG COMPOUND
Database Links Databases
1005 DrugCentral
C06977 KEGG COMPOUND
CPD0-2065 MetaCyc
D07892 KEGG DRUG
DB00584 DrugBank
Enalapril Wikipedia
EP12401 Patent
HMDB0014722 HMDB
LSM-3282 LINCS
US4374829 Patent
View more database links
Registry Numbers Types Sources
3657467 Beilstein Registry Number Beilstein
75847-73-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10669559 PubMed citation ChEMBL
23030053 PubMed citation Europe PMC
23413003 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-03-18 Following oral administration, esterases hydrolyse the ethyl ester group to afford the corresponding carboxylic acid, enalaprilat, an angiotensin-converting enzyme (ACE) inhibitor. Enalapril is thus a prodrug for enalaprilat (which, unlike enalapril, is not absorbed by mouth) and is used as the maleate salt in the treatment of hypertension and heart failure, for reduction of proteinuria and renal disease in patients with nephropathies, and for the prevention of stroke, myocardial infarction, and cardiac death in high-risk patients.