donepezil   Click here for help

GtoPdb Ligand ID: 6599

Synonyms: Aricept® | E-2020
Approved drug
donepezil is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: May be refered to as donepezil hydrochloride (PubChem CID 5741). In addition to the original brand, Aricept, generic donepezil formulations are now approved by the US FDA.
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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

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: donepezil

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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Click here for structure editor
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 2
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 38.77
Molecular weight 379.21
XLogP 3.67
No. Lipinski's rules broken 0
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 COc1cc2c(cc1OC)CC(C2=O)CC1CCN(CC1)Cc1ccccc1
Isomeric SMILES COc1cc2c(cc1OC)CC(C2=O)CC1CCN(CC1)Cc1ccccc1
InChI InChI=1S/C24H29NO3/c1-27-22-14-19-13-20(24(26)21(19)15-23(22)28-2)12-17-8-10-25(11-9-17)16-18-6-4-3-5-7-18/h3-7,14-15,17,20H,8-13,16H2,1-2H3
InChI Key ADEBPBSSDYVVLD-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996))
IUPAC Name Click here for help
5,6-dimethoxy-2-[[1-(phenylmethyl)piperidin-4-yl]methyl]-2,3-dihydroinden-1-one
International Nonproprietary Names Click here for help
INN number INN
7517 donepezil
Synonyms Click here for help
Aricept® | E-2020
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9635088
Reactome Reaction Reactome logo R-HSA-9634834
Other databases
CAS Registry No. 120014-06-4
ChEMBL Ligand CHEMBL502
DrugBank Ligand DB00843
DrugCentral Ligand 946
GtoPdb PubChem SID 178103212
PubChem CID 3152
Search Google for chemical match using the InChIKey ADEBPBSSDYVVLD-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ADEBPBSSDYVVLD
Search PubMed clinical trials donepezil
Search PubMed titles donepezil
Search PubMed titles/abstracts donepezil
SynPHARM 78555 (in complex with acetylcholinesterase (Cartwright blood group))
UniChem Compound Search for chemical match using the InChIKey ADEBPBSSDYVVLD-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ADEBPBSSDYVVLD-UHFFFAOYSA-N
Wikipedia Donepezil