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.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: fosinopril

2D Structure
Click here for help

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.

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

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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
InChI Key BIDNLKIUORFRQP-XYGFDPSESA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1991)
Is prodrug? Yes
Active form fosinoprilat
IUPAC Name Click here for help
(2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5833 fosinopril
Synonyms Click here for help
Monopril® | SQ-28555
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9619057
Reactome Reaction Reactome logo R-HSA-9619024
Other databases
CAS Registry No. 98048-97-6 (source: PubChem)
ChEBI CHEBI:5163
ChEMBL Ligand CHEMBL3039598
DrugBank Ligand DB00492
DrugCentral Ligand 1245, 1245
GtoPdb PubChem SID 178103071
PubChem CID 9601226
Search Google for chemical match using the InChIKey BIDNLKIUORFRQP-XYGFDPSESA-N
Search Google for chemicals with the same backbone BIDNLKIUORFRQP
Search PubMed clinical trials fosinopril
Search PubMed titles fosinopril
Search PubMed titles/abstracts fosinopril
UniChem Compound Search for chemical match using the InChIKey BIDNLKIUORFRQP-XYGFDPSESA-N
UniChem Connectivity Search for chemical match using the InChIKey BIDNLKIUORFRQP-XYGFDPSESA-N
Wikipedia Fosinopril