CHEBI:4786 - enalaprilat (anhydrous)

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ChEBI Name enalaprilat (anhydrous)
ChEBI ID CHEBI:4786
Definition Enalapril in which the ethyl ester group has been hydrolysed to the corresponding carboxylic acid. Enalaprilat is an angiotensin-converting enzyme (ACE) inhibitor and is used (often in the form of its prodrug, enalapril) 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. Unlike enalapril, enalaprilat is not absorbed by mouth but is given by intravenous injection, usually as the dihydrate.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:123355
Supplier Information
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Formula C18H24N2O5
Net Charge 0
Average Mass 348.39360
Monoisotopic Mass 348.169
InChI InChI=1S/C18H24N2O5/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25)/t12-,14-,15-/m0/s1
InChIKey LZFZMUMEGBBDTC-QEJZJMRPSA-N
SMILES C[C@H](N[C@@H](CCc1ccccc1)C(O)=O)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): 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.
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ChEBI Ontology
Outgoing enalaprilat (anhydrous) (CHEBI:4786) has role antihypertensive agent (CHEBI:35674)
enalaprilat (anhydrous) (CHEBI:4786) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
enalaprilat (anhydrous) (CHEBI:4786) is a dicarboxylic acid (CHEBI:35692)
enalaprilat (anhydrous) (CHEBI:4786) is a dipeptide (CHEBI:46761)
Incoming enalapril (CHEBI:4784) has functional parent enalaprilat (anhydrous) (CHEBI:4786)
enalaprilat dihydrate (CHEBI:59877) has part enalaprilat (anhydrous) (CHEBI:4786)
IUPAC Name
N-[(1S)-1-carboxy-3-phenylpropyl]-L-alanyl-L-proline
Synonyms Sources
enalapril acid ChemIDplus
enalapril diacid ChemIDplus
Enalaprilat KEGG COMPOUND
enalaprilat ChemIDplus
enalaprilat anhydrous ChemIDplus
enalaprilate ChemIDplus
enalaprilatum ChemIDplus
Database Links Databases
C11720 KEGG COMPOUND
DB00584 DrugBank
EAL PDBeChem
EP12401 Patent
LSM-6026 LINCS
US4374829 Patent
View more database links
Registry Numbers Types Sources
3656856 Beilstein Registry Number Beilstein
76420-72-9 CAS Registry Number ChemIDplus
Last Modified
25 February 2016