kynurenic acid   Click here for help

GtoPdb Ligand ID: 2918

Abbreviated name: KYNA
Synonyms: transtorine
PDB Ligand
Comment: Kynurenic acid is a by-product of the kynurenine pathway, the main route for the non-protein metabolism (catabolism) of tryptophan [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 70.16
Molecular weight 189.04
XLogP 2.43
No. Lipinski's rules broken 0
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Canonical SMILES OC(=O)c1cc(=O)c2c([nH]1)cccc2
Isomeric SMILES OC(=O)c1cc(=O)c2c([nH]1)cccc2
InChI InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)
1. Moroni F, Cozzi A, Sili M, Mannaioni G. (2012)
Kynurenic acid: a metabolite with multiple actions and multiple targets in brain and periphery.
J Neural Transm (Vienna), 119 (2): 133-9. [PMID:22215208]
2. Southern C, Cook JM, Neetoo-Isseljee Z, Taylor DL, Kettleborough CA, Merritt A, Bassoni DL, Raab WJ, Quinn E, Wehrman TS et al.. (2013)
Screening β-Arrestin Recruitment for the Identification of Natural Ligands for Orphan G-Protein-Coupled Receptors.
J Biomol Screen, 18 (5): 599-609. [PMID:23396314]
3. Wang J, Simonavicius N, Wu X, Swaminath G, Reagan J, Tian H, Ling L. (2006)
Kynurenic acid as a ligand for orphan G protein-coupled receptor GPR35.
J Biol Chem, 281 (31): 22021-8. [PMID:16754668]
4. Wirthgen E, Hoeflich A. (2015)
Endotoxin-Induced Tryptophan Degradation along the Kynurenine Pathway: The Role of Indolamine 2,3-Dioxygenase and Aryl Hydrocarbon Receptor-Mediated Immunosuppressive Effects in Endotoxin Tolerance and Cancer and Its Implications for Immunoparalysis.
J Amino Acids, 2015: 973548. [PMID:26881062]