indole-3-carbinol   Click here for help

GtoPdb Ligand ID: 10047

Synonyms: 3-hydroxymethylindole | 3-indolemethanol | 3-indolylcarbinol | I3C
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Indole-3-carbinol (I3C) is a secondary plant metabolite produced in Brassica family vegetables. It has been reported as an aryl hydrocarbon receptor agonist, although its affinity is very low and it therefore may not be a significant agonist of the AhR in vivo [2]. Anticarcinogenic and antitumourigenic properties of I3C have been reported in various types of cancer cells [1,3-4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 36.02
Molecular weight 147.07
XLogP 1.75
No. Lipinski's rules broken 0
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Canonical SMILES OCc1c[nH]c2c1cccc2
Isomeric SMILES OCc1c[nH]c2c1cccc2
InChI InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
1. Aggarwal BB, Ichikawa H. (2005)
Molecular targets and anticancer potential of indole-3-carbinol and its derivatives.
Cell Cycle, 4 (9): 1201-15. [PMID:16082211]
2. Bjeldanes LF, Kim JY, Grose KR, Bartholomew JC, Bradfield CA. (1991)
Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: comparisons with 2,3,7,8-tetrachlorodibenzo-p-dioxin.
Proc Natl Acad Sci USA, 88 (21): 9543-7. [PMID:1658785]
3. Metidji A, Omenetti S, Crotta S, Li Y, Nye E, Ross E, Li V, Maradana MR, Schiering C, Stockinger B. (2018)
The Environmental Sensor AHR Protects from Inflammatory Damage by Maintaining Intestinal Stem Cell Homeostasis and Barrier Integrity.
Immunity, 49 (2): 353-362.e5. DOI: 10.1016/j.immuni.2018.07.010 [PMID:30119997]
4. Rogan EG. (2006)
The natural chemopreventive compound indole-3-carbinol: state of the science.
In Vivo, 20 (2): 221-8. [PMID:16634522]