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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: lisinopril

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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 Model List of Essential Medicines (21st List, 2019). Access PDF version.
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
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
Search UniChem for chemical match using the InChIKey RLAWWYSOJDYHDC-BZSNNMDCSA-N
Search UniChem for chemicals with the same backbone RLAWWYSOJDYHDC
SynPHARM 78461 (in complex with Angiotensin-converting enzyme)
Wikipedia Lisinopril