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CHEBI:88200 - benazeprilat

ChEBI IDCHEBI:88200
ChEBI Namebenazeprilat
Stars
DefinitionA benzazepine that is 1,3,4,5-tetrahydro-2H-1-benzazepin-2-one in which the hydrogen attached to the nitrogen is replaced by a carboxy methyl group and in which the 3-pro-S hydrogen is replaced by the amino group of (2S)-2-amino-4-phenylbutanoic acid. An angiotensin-converting enzyme inhibitor, it is used as its monoester prodrug benazepril in the treatment of hypertension and heart failure.
Last Modified13 October 2015
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H24N2O5
Net Charge0
Average Mass396.443
Monoisotopic Mass396.16852
SMILES[H][C@]1(N[C@@H](CCc2ccccc2)C(=O)O)CCc2ccccc2N(CC(=O)O)C1=O
InChIInChI=1S/C22H24N2O5/c25-20(26)14-24-19-9-5-4-8-16(19)11-13-17(21(24)27)23-18(22(28)29)12-10-15-6-2-1-3-7-15/h1-9,17-18,23H,10-14H2,(H,25,26)(H,28,29)/t17-,18-/m0/s1
InChIKeyMADRIHWFJGRSBP-ROUUACIJSA-N
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).
Application:
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)
benazeprilat (CHEBI:88200) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
benazeprilat (CHEBI:88200) is a benzazepine (CHEBI:35676)
benazeprilat (CHEBI:88200) is a dicarboxylic acid (CHEBI:35692)
benazeprilat (CHEBI:88200) is a lactam (CHEBI:24995)
Incoming Relation(s)
benazepril (CHEBI:3011) has functional parent benazeprilat (CHEBI:88200)
IUPAC Name 
(2S)-2-{[(3S)-1-(carboxymethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-4-phenylbutanoic acid
INNs  Source
benazeprilatIUPAC
benazeprilatumIUPAC
benazeprilatIUPAC
bénazéprilateIUPAC
Synonyms  Source
CGS 14831ChemIDplus
(3S)-3-(((1S)-1-carboxy-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acidChemIDplus
benazepril diacidChEBI
Manual XrefsDatabases
D03077KEGG DRUG
HMDB0060582HMDB
Registry NumbersSources
Reaxys:4214792Reaxys
CAS:86541-78-8ChemIDplus