fosinopril   Click here for help

GtoPdb Ligand ID: 6456

Synonyms: Monopril® | SQ-28555
Approved drug
fosinopril is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Fosinopril is a prodrug which is metabolised to the active drug fosinoprilat. Fosinopril belongs to the angiotensin-converting enzyme (ACE) inhibitor drug family. There is some ambiguity in the literature and on other resources as to the exact stereochemistry of fosinopril. The structure shown here matches that specified by the INN document.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: fosinopril

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 1
Rotatable bonds 16
Topological polar surface area 120.02
Molecular weight 563.3
XLogP 6.31
No. Lipinski's rules broken 2
Click here for help
Canonical SMILES CCC(=O)OC(C(C)C)OP(=O)(CC(=O)N1CC(CC1C(=O)O)C1CCCCC1)CCCCc1ccccc1
Isomeric SMILES CCC(=O)O[C@H](C(C)C)O[P@@](=O)(CC(=O)N1C[C@@H](C[C@H]1C(=O)O)C1CCCCC1)CCCCc1ccccc1
InChI InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30+,39-/m1/s1
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Angiotensin-converting enzyme Primary target of this compound Hs Inhibitor Inhibition - - -