lenabasum   Click here for help

GtoPdb Ligand ID: 9772

Synonyms: ajulemic acid | CPL-7075 | CPL7075 | CT-3 | IP-751 | IP751
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Lenabasum (ajulemic acid) is a synthetic derivative of the non-psychoactive cannabinoid THC metabolite 11-nor-9-Carboxy-THC (PubChem CID 108207) [10]. It is a non-selective cannabinoid receptor agonist [5,7]. Lenabasum exhibits potentially useful analgesic and anti-inflammatory actions [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 66.76
Molecular weight 400.26
XLogP 6.96
No. Lipinski's rules broken 1
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Canonical SMILES CCCCCCC(c1cc(O)c2c(c1)OC(C1C2CC(=CC1)C(=O)O)(C)C)(C)C
Isomeric SMILES CCCCCCC(c1cc(O)c2c(c1)OC([C@H]1[C@H]2CC(=CC1)C(=O)O)(C)C)(C)C
InChI InChI=1S/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10,14-15,18-19,26H,6-9,11-13H2,1-5H3,(H,27,28)/t18-,19-/m1/s1
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CB1 receptor Hs Agonist Agonist 7.5 pKi - 5,7
pKi 7.5 (Ki 3.23x10-8 M) [5,7]
CB2 receptor Hs Agonist Agonist 6.8 pKi - 5,7
pKi 6.8 (Ki 1.7x10-7 M) [5,7]