compound 3 [PMID: 23134120]   Click here for help

GtoPdb Ligand ID: 9190

Synonyms: HS6666
Compound class: Synthetic organic
Comment: Compound 3 is a partial agonist of the κ opioid receptor [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 23.47
Molecular weight 295.19
XLogP 4.13
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Oc1cccc(c1)CCN(CC1CC1)CCc1ccccc1
Isomeric SMILES Oc1cccc(c1)CCN(CC1CC1)CCc1ccccc1
InChI InChI=1S/C20H25NO/c22-20-8-4-7-18(15-20)12-14-21(16-19-9-10-19)13-11-17-5-2-1-3-6-17/h1-8,15,19,22H,9-14,16H2
InChI Key QURAQIGQNZYJHP-UHFFFAOYSA-N
Bioactivity Comments
Whilst compound 3 shows weak agonist activity at the μ opioid receptor, and the dopamine D2 and D3 receptors, it is inactive at the δ opioid receptor and D1 receptor [1].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
κ receptor Hs Agonist Partial agonist 8.2 pKi - 1
pKi 8.2 (Ki 5.9x10-9 M) [1]
D2 receptor Hs Agonist Agonist 6.9 pKi - 1
pKi 6.9 (Ki 1.18x10-7 M) [1]
D3 receptor Hs Agonist Agonist 6.8 pKi - 1
pKi 6.8 (Ki 1.68x10-7 M) [1]
μ receptor Hs Agonist Agonist 6.1 pKi - 1
pKi 6.1 (Ki 8.26x10-7 M) [1]
κ receptor Hs Agonist Partial agonist 7.5 pEC50 - 1
pEC50 7.5 (EC50 3.5x10-8 M) [1]
Description: Measuring stimulation of [35S]GTPγS binding.