Sch.336   Click here for help

GtoPdb Ligand ID: 9799

Synonyms: analog 4j [PMID: 15664857] | SCH-336 | SCH336
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Sch.336 is a novel inverse agonist that is selective for the cannabinoid receptor CB2 that is expressed on peripheral immune cells [1-2]. It is suitable for in vitro and in vivo studies.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 158.05
Molecular weight 539.07
XLogP 3.43
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc(c(c1)S(=O)(=O)c1ccc(cc1)OC)S(=O)(=O)c1ccc(cc1)C(NS(=O)(=O)C)C
Isomeric SMILES COc1ccc(c(c1)S(=O)(=O)c1ccc(cc1)OC)S(=O)(=O)c1ccc(cc1)[C@@H](NS(=O)(=O)C)C
InChI InChI=1S/C23H25NO8S3/c1-16(24-33(4,25)26)17-5-10-20(11-6-17)34(27,28)22-14-9-19(32-3)15-23(22)35(29,30)21-12-7-18(31-2)8-13-21/h5-16,24H,1-4H3/t16-/m0/s1
Bioactivity Comments
The inverse agonist action of Sch.336 is demonstrated in three different assays formats, including measuring its ability to decrease ligand-induced GTPγS binding to human CB2 receptors in vitro (EC50 2 nM) [2].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CB2 receptor Primary target of this compound Hs Agonist Inverse agonist 8.7 – 9.4 pKi - 1-2
pKi 9.4 (Ki 4x10-10 M) [1]
pKi 8.7 (Ki 1.8x10-9 M) [2]
Description: Measuring competitin binding with [3H]CP55,940 for binding to human CB2 on Sf9 cell membranes.
CB1 receptor Hs Agonist Inverse agonist 6.0 pKi - 1
pKi 6.0 (Ki 9.05x10-7 M) [1]
CB1 receptor Hs Agonist Inverse agonist 6.7 pEC50 - 2
pEC50 6.7 (EC50 2x10-7 M) [2]