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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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1987))
WHO Essential Medicine WHO Essential Medicines List (EML) (22nd List, 2021). Access PDF version.
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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)
ChEMBL Ligand CHEMBL1237
DrugBank Ligand DB00722
DrugCentral Ligand 1587
GtoPdb PubChem SID 178102978
PubChem CID 5362119
Search Google for chemical match using the InChIKey RLAWWYSOJDYHDC-BZSNNMDCSA-N
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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