lisinopril   Click here for help

GtoPdb Ligand ID: 6360

Synonyms: Prinivil® | Zestril®
Approved drug PDB Ligand
lisinopril is an approved drug (FDA (1987))
Compound class: Synthetic organic
Comment: Lisinopril was the third ACE inhibitor (after captopril and enalapril) to be approved for clinical use. Chemically it is the lysine analogue of enalapril. Unlike other ACE inhibitors, it is not a prodrug and is excreted unchanged in the urine.
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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

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View more information in the IUPHAR Pharmacology Education Project: lisinopril

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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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 8
Hydrogen bond donors 4
Rotatable bonds 13
Topological polar surface area 132.96
Molecular weight 405.23
XLogP -0.93
No. Lipinski's rules broken 1
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 NCCCCC(C(=O)N1CCCC1C(=O)O)NC(C(=O)O)CCc1ccccc1
Isomeric SMILES NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N[C@H](C(=O)O)CCc1ccccc1
InChI InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1
InChI Key RLAWWYSOJDYHDC-BZSNNMDCSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1987))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2S)-1-[(2S)-6-amino-2-[[(2S)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5425 lisinopril
Synonyms Click here for help
Prinivil® | Zestril®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9614909
Reactome Reaction Reactome logo R-HSA-9614933
Other databases
CAS Registry No. 76547-98-3 (source: PubChem)
ChEBI CHEBI:43755
ChEMBL Ligand CHEMBL1237
DrugBank Ligand DB00722
DrugCentral Ligand 1587
GtoPdb PubChem SID 178102978
PubChem CID 5362119
RCSB PDB Ligand LPR
Search Google for chemical match using the InChIKey RLAWWYSOJDYHDC-BZSNNMDCSA-N
Search Google for chemicals with the same backbone RLAWWYSOJDYHDC
Search PubMed clinical trials lisinopril
Search PubMed titles lisinopril
Search PubMed titles/abstracts lisinopril
SynPHARM 78461 (in complex with Angiotensin-converting enzyme)
UniChem Compound Search for chemical match using the InChIKey RLAWWYSOJDYHDC-BZSNNMDCSA-N
UniChem Connectivity Search for chemical match using the InChIKey RLAWWYSOJDYHDC-BZSNNMDCSA-N
Wikipedia Lisinopril