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.
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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
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 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 1
Rotatable bonds 3
Topological polar surface area 38.91
Molecular weight 198.12
XLogP 1.95
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 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
References
1. Cook D, Brown D, Alexander R, March R, Morgan P, Satterthwaite G, Pangalos MN. (2014)
Lessons learned from the fate of AstraZeneca's drug pipeline: a five-dimensional framework.
Nat Rev Drug Discov, 13 (6): 419-31. [PMID:24833294]
2. Monaghan DT, Larsen H. (1997)
NR1 and NR2 subunit contributions to N-methyl-D-aspartate receptor channel blocker pharmacology.
J Pharmacol Exp Ther, 280 (2): 614-20. [PMID:9023271]
3. Zarate Jr CA, Mathews D, Ibrahim L, Chaves JF, Marquardt C, Ukoh I, Jolkovsky L, Brutsche NE, Smith MA, Luckenbaugh DA. (2013)
A randomized trial of a low-trapping nonselective N-methyl-D-aspartate channel blocker in major depression.
Biol Psychiatry, 74 (4): 257-64. [PMID:23206319]