indolo[3,2-b]carbazole   Click here for help

GtoPdb Ligand ID: 10046

Synonyms: ICZ | ICZ-carbazole
Compound class: Synthetic organic
Comment: Indolo(3,2-b)carbazole is a potent agonist of the aryl hydrocarbon receptor (AhR) [1]. It is a metabolite of indole-3-carbinol (I3C) whihc is found in Brassica family vegetables, and which is formed in the acid pH of the stomach.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 24.72
Molecular weight 254.08
XLogP 4.29
No. Lipinski's rules broken 0
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Canonical SMILES c1ccc2c(c1)c1cc3=Nc4c(c3cc1=N2)cccc4
Isomeric SMILES c1ccc2c(c1)c1cc3=Nc4c(c3cc1=N2)cccc4
InChI InChI=1S/C18H10N2/c1-3-7-15-11(5-1)13-9-18-14(10-17(13)19-15)12-6-2-4-8-16(12)20-18/h1-10H
Bioactivity Comments
In vivo, indolo(3,2-b)carbazole induces cytochrome P4501A1 activity with an EC50 of 269 nM (in murine hepatoma Hepa 1c1c7 cells using an assay that measures ethoxyresorufin O-deethylase activity) [1].
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Aryl hydrocarbon receptor Mm Agonist Agonist 9.7 pKd - 1
pKd 9.7 (Kd 1.9x10-10 M) [1]
Description: Radioligand displacement binding of [2-1251]7,8-dibromodibenzo-pdioxin to AhR prepared from C57BL/6J mouse liver cytosol.