indolo[3,2-b]carbazole   

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.
2D Structure
Click here for structure editor
Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key HLVSZSQYBQCBQG-UHFFFAOYSA-N
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
Key to terms and symbols Click column headers to sort
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.