benazepril   Click here for help

GtoPdb Ligand ID: 6374

Synonyms: CGS-14824A | Lotensin®
Approved drug
benazepril is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Benazepril (an ACE inhibitor) is administered as an ester is a prodrug, which is metabolized by the liver into its active form benazeprilat.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: benazepril

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 95.94
Molecular weight 424.2
XLogP 3.28
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCOC(=O)C(NC1CCc2c(N(C1=O)CC(=O)O)cccc2)CCc1ccccc1
Isomeric SMILES CCOC(=O)[C@@H](N[C@H]1CCc2c(N(C1=O)CC(=O)O)cccc2)CCc1ccccc1
InChI InChI=1S/C24H28N2O5/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28)/t19-,20-/m0/s1
InChI Key XPCFTKFZXHTYIP-PMACEKPBSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1991))
Is prodrug? Yes
Active form benazeprilat
IUPAC Name Click here for help
2-[(3S)-3-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid
International Nonproprietary Names Click here for help
INN number INN
6129 benazepril
Synonyms Click here for help
CGS-14824A | Lotensin®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9619005
Reactome Reaction Reactome logo R-HSA-9619024
Other databases
CAS Registry No. 86541-75-5 (source: PubChem)
ChEBI CHEBI:3011
ChEMBL Ligand CHEMBL838
DrugBank Ligand DB00542
DrugCentral Ligand 299, 299
GtoPdb PubChem SID 178102992
PubChem CID 5362124
Search Google for chemical match using the InChIKey XPCFTKFZXHTYIP-PMACEKPBSA-N
Search Google for chemicals with the same backbone XPCFTKFZXHTYIP
Search PubMed clinical trials benazepril
Search PubMed titles benazepril
Search PubMed titles/abstracts benazepril
UniChem Compound Search for chemical match using the InChIKey XPCFTKFZXHTYIP-PMACEKPBSA-N
UniChem Connectivity Search for chemical match using the InChIKey XPCFTKFZXHTYIP-PMACEKPBSA-N
Wikipedia Benazepril