AM1710   Click here for help

GtoPdb Ligand ID: 10202

Synonyms: AM-1710 | analog 4b [PMID: 18038967]
Compound class: Synthetic organic
Comment: AM1710 is a cannabilactone class, selective cannabinoid CB2 receptor agonist [5]. The cannabilactones produce peripheral analgesic activity without the the psychoactive central nervous system side-effects of other CB2 receptor agonists [3]. As expected from its pharmacological profile, AM1710 shows limited blood brain barrier penetration [5]. It has potent agonist activity at rat and mouse CB2 receptors but much reduced activity at human receptors, so is an excellent tool for rodent studies, but it is less useful for translation-to-human studies. In vitro experiments have identified low-potency CB1 inverse agonist activity, but the in vivo relevance of this discovery is undetermined [2].It is important to note that the sequence heterogeneity in CB2 across species leads to different pharmacologic responses to identical drugs [1], so extrapolating results from rodent models to humans should be approached with caution.
A 2019 publication of work by Li et al. describes rodent experiments that they undertook to resolve the mechanism(s) by which AM1710 suppresses allodynia caused by distinct pathological processes [4]. Their investigations show that AM1710 is not a broad-spectrum analgesic. In rodent models it is effective in paclitaxel-induced mechanical and cold allodynia but not in mechanically-induced allodynia.
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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 0
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 59.67
Molecular weight 368.2
XLogP 8.09
No. Lipinski's rules broken 1

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 CCCCCCC(c1cc(O)c2c(c1)oc(=O)c1c2cc(OC)cc1)(C)C
Isomeric SMILES CCCCCCC(c1cc(O)c2c(c1)oc(=O)c1c2cc(OC)cc1)(C)C
InChI InChI=1S/C23H28O4/c1-5-6-7-8-11-23(2,3)15-12-19(24)21-18-14-16(26-4)9-10-17(18)22(25)27-20(21)13-15/h9-10,12-14,24H,5-8,11H2,1-4H3
InChI Key ZAIKPEWFCSQNQB-UHFFFAOYSA-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
1-hydroxy-9-methoxy-3-(2-methyloctan-2-yl)benzo[c]chromen-6-one
Synonyms Click here for help
AM-1710 | analog 4b [PMID: 18038967]
Database Links Click here for help
Specialist databases
GPCRdb Ligand AM1710
Other databases
BindingDB Ligand 50228073
ChEMBL Ligand CHEMBL266712
GtoPdb PubChem SID 381118912
PubChem CID 11268660
Search Google for chemical match using the InChIKey ZAIKPEWFCSQNQB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ZAIKPEWFCSQNQB
UniChem Compound Search for chemical match using the InChIKey ZAIKPEWFCSQNQB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZAIKPEWFCSQNQB-UHFFFAOYSA-N