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lanicemine   Click here for help

GtoPdb Ligand ID: 7681

Synonyms: AR-R15896AR | ARL 15896 | AZD-6765 | AZD6765
Compound class: Synthetic organic
Comment: Lanicemine (AZD 6765) was originally developed as a neuroprotective agent, but was repurposed as an antidepressant with potential for the management of severe and treatment-resistant depression [3]. However, the compound failed to meet study endpoints, so development was halted. The compound is discussed in the AZ 2014 review paper [1].
The structure represented here shows stereochemistry identical to the INN record wheras PubChem CID 3038485 represents the non-chiral molecule.
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 3
Topological polar surface area 38.91
Molecular weight 198.12
XLogP 1.95
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 NC(c1ccccc1)Cc1ccccn1
Isomeric SMILES N[C@H](c1ccccc1)Cc1ccccn1
InChI InChI=1S/C13H14N2/c14-13(11-6-2-1-3-7-11)10-12-8-4-5-9-15-12/h1-9,13H,10,14H2/t13-/m0/s1
InChI Key FWUQWDCOOWEXRY-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
IUPAC Name Click here for help
(1S)-1-phenyl-2-pyridin-2-ylethanamine
International Nonproprietary Names Click here for help
INN number INN
7943 lanicemine
Synonyms Click here for help
AR-R15896AR | ARL 15896 | AZD-6765 | AZD6765
Database Links Click here for help
CAS Registry No. 153322-05-5 (source: SciFinder)
ChEMBL Ligand CHEMBL467084
GtoPdb PubChem SID 223366016
PubChem CID 9794203
Search Google for chemical match using the InChIKey FWUQWDCOOWEXRY-ZDUSSCGKSA-N
Search Google for chemicals with the same backbone FWUQWDCOOWEXRY
Search PubMed clinical trials lanicemine
Search PubMed titles lanicemine
Search PubMed titles/abstracts lanicemine
UniChem Compound Search for chemical match using the InChIKey FWUQWDCOOWEXRY-ZDUSSCGKSA-N
UniChem Connectivity Search for chemical match using the InChIKey FWUQWDCOOWEXRY-ZDUSSCGKSA-N
Wikipedia Lanicemine