3-Hydroxyanthranilic acid

3-Hydroxyanthranilic Acid

Structure of 3-Hydroxyanthranilic acid

3D model of 3-Hydroxyanthranilic acid zwitterion

3-Hydroxyanthranilic acid is an organic compound with the formula C₇H₇NO₃. It is a derivative of anthranilic acid and is an important intermediate in the tryptophan metabolism pathway.

Structure and Properties

3-Hydroxyanthranilic acid is characterized by a benzene ring substituted with a hydroxyl group and an amino group, making it an aromatic amino acid. It exists in a zwitterionic form in solution, where the amino group is protonated and the carboxyl group is deprotonated.

Biosynthesis

3-Hydroxyanthranilic acid is produced in the body from tryptophan through the kynurenine pathway. This pathway involves the conversion of tryptophan to kynurenine, which is then hydroxylated to form 3-hydroxykynurenine. 3-Hydroxykynurenine is subsequently cleaved to produce 3-hydroxyanthranilic acid.

Biological Role

In the kynurenine pathway, 3-hydroxyanthranilic acid serves as a precursor to quinolinic acid, which is a key intermediate in the biosynthesis of nicotinamide adenine dinucleotide (NAD⁺). This pathway is crucial for maintaining cellular energy balance and redox status.

Clinical Significance

Alterations in the levels of 3-hydroxyanthranilic acid have been associated with various diseases, including neurodegenerative disorders and inflammatory diseases. It has been studied for its potential role in modulating immune responses and its involvement in the pathogenesis of conditions such as Alzheimer's disease and Parkinson's disease.

Related Compounds

• Anthranilic acid
• Kynurenine
• Quinolinic acid
• Nicotinamide adenine dinucleotide

Related Pages

• Tryptophan metabolism
• Kynurenine pathway
• Neurodegenerative disorders

3-Hydroxyanthranilic_acid

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  3-Hydroxyanthranilic acid structure
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  3-Hydroxyanthranilic acid zwitterion 3D model