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Cinnabarinic acid is a phenoxazinone produced by the oxidative dimerization of 3-hydroxyanthranilic acid (3-HAA) as part of the metabolism of tryptophan in the kynurenic pathway. It acts as a partial receptor agonist of the metabotropic glutamate receptor 4 (mGlu4), effective at 100 μM, with no activity at other mGlu receptor subtypes. 3-HAA does not affect mGlu receptors, including mGlu4. Cinnabarinic acid induces apoptosis of T cells at 300-500 μM, a potency some ten times that of 3-HAA.

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A natural phenoxazinone deriv Cin nabarinic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase.

ChEBI: Cinnavalininate is a phenoxazine.

Cinnabarinic acid is a kynurenine pathway metabolite of tryptophan, produced by the oxidation of 3-Hydroxyanthranilic acid. Cinnabarinic acid leads to loss of mitochondrial respiration and apoptosis, and has also been shown to be an mGlu4R-specific agonist.

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1) Lowe?et al.?(2014),?Identification of cinnabarinic acid as a novel endogenous aryl hydrocarbon receptor ligand that drives IL-22 production;? PLoS One,?9(2)?e87877 2) Hiramatsu?et al. (2008),?Cinnabarinic acid generated from 3-hydroxyanthranilic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase;? J. Cell. Biochem.,?103?42 3) Fazio?et al.?(2012),?Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors;? Mol. Pharmacol.,?81?643