esketamine   Click here for help

GtoPdb Ligand ID: 9152

Synonyms: (S)-Ketamine | Spravato®
Approved drug PDB Ligand
esketamine is an approved drug (EMA & FDA (2019))
Compound class: Synthetic organic
Comment: As the ketamine (S) enatiomer esketamine is twice as potent and has a more medically useful pharmacological action than racemic ketamine. Part of this advantage arises from inhibition of dopamine transporters.
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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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 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.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 29.1
Molecular weight 237.09
XLogP 2.88
No. Lipinski's rules broken 0

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
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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.

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/)

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Canonical SMILES CNC1(CCCCC1=O)c1ccccc1Cl
Isomeric SMILES CN[C@@]1(CCCCC1=O)c1ccccc1Cl
InChI InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3/t13-/m0/s1
InChI Key YQEZLKZALYSWHR-ZDUSSCGKSA-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 (2019)  |  EMA (2019)
IUPAC Name Click here for help
(2S)-2-(2-chlorophenyl)-2-methylaminocyclohexan-1-one
International Nonproprietary Names Click here for help
INN number INN
7884 esketamine
Synonyms Click here for help
(S)-Ketamine | Spravato®
Database Links Click here for help
ChEMBL Ligand CHEMBL395091
DrugCentral Ligand 4468
GtoPdb PubChem SID 315661237
PubChem CID 182137
RCSB PDB Ligand JC9
Search Google for chemical match using the InChIKey YQEZLKZALYSWHR-ZDUSSCGKSA-N
Search Google for chemicals with the same backbone YQEZLKZALYSWHR
Search PubMed clinical trials esketamine
Search PubMed titles esketamine
Search PubMed titles/abstracts esketamine
UniChem Compound Search for chemical match using the InChIKey YQEZLKZALYSWHR-ZDUSSCGKSA-N
UniChem Connectivity Search for chemical match using the InChIKey YQEZLKZALYSWHR-ZDUSSCGKSA-N
Wikipedia Esketamine