selonabant   Click here for help

GtoPdb Ligand ID: 13511

Synonyms: ANEB-001 | ANEB001
Compound class: Synthetic organic
Comment: The chemical structure for selonabant was obtained from WHO proposed INN list 131 (August 2024). The INN record describes the compound as a cannabinoid receptor 1 (CB1) antagonist. A chemical structure match via PubChem indicates that this is the INN for Anebulo Pharmaceutical's clinical lead ANEB-001, which is a high affinity, competitive CB1 antagonist. It is proposed as a rapidly acting antidote for acute cannabinoid intoxication. The structure for selonabant was originally claimed in a Vernalis patent [1] (named V24343 by Vernalis), but it is claimed specifically as ANEB-001 in WO2022109043A1 [2].
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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 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 4
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 41.57
Molecular weight 440.89
XLogP 3.09
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 CC(C)(C)NC(=O)N1CC(C1)O[C@H](C2=CC=C(C=C2)Cl)C3=C(C=CC=C3)C(F)(F)F
Isomeric SMILES C(C)(C)(C)NC(=O)N1CC(C1)O[C@@H](C2=C(C=CC=C2)C(F)(F)F)C3=CC=C(C=C3)Cl
InChI InChI=1S/C22H24ClF3N2O2/c1-21(2,3)27-20(29)28-12-16(13-28)30-19(14-8-10-15(23)11-9-14)17-6-4-5-7-18(17)22(24,25)26/h4-11,16,19H,12-13H2,1-3H3,(H,27,29)/t19-/m1/s1
InChI Key BNLYOVHLLDBOFZ-LJQANCHMSA-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/)
Bioactivity Comments
The affinity value provided is for the compound claimed as Example 81 in [1], but note that 81 has no specified sterocenter.
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CB1 receptor Hs Antagonist Antagonist 8.6 pKi - 1
⤷ pKi 8.6 (Ki 2.3x10-9 M) [1]
Description: Determined in a displacement binding assay using membranes from HEK cells expressing hCB1 receptors and [3H]-SR-141716A as tracer