Details of Metabolite

General Information of MET (ID: META00299)
Name L-Kynurenine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoate; (2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid; (AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoate; (AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoic acid; (S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoate; (S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acid; 3-(3-Hydroxyanthraniloyl)-L-alanine; 3-Anthraniloyl-L-alanine; 3-Anthraniloyl-alanine; 3-Anthraniloylalanine; 3-Hydroxy-L-kynurenine; DL-Kynurenine; DL-Kynureninefree base; KYNURENINE; Kynurenin; Quinurenine; alpha,2-Diamino-gamma-oxo-benzenebutanoate; alpha,2-Diamino-gamma-oxo-benzenebutanoic acid
Source Endogenous;Yeast Metabolite;Food;Drug;Microbial
Structure Type   Carbonyl compounds  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic oxygen compounds
Organooxygen compounds
Carbonyl compounds
PubChem CID
161166
HMDB ID
HMDB0000684
Formula
C10H12N2O3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00328
DrugBank ID
DB02070
ChEBI ID
16946
FooDB ID
FDB022181
ChemSpider ID
141580
METLIN ID
72
Physicochemical Properties Molecular Weight 208.21 Topological Polar Surface Area 106
XlogP -2.2 Complexity 255
Heavy Atom Count 15 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Function
Kynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. L-Kynurenine is a central compound of the tryptophan metabolism pathway since it can change into the neuroprotective agent kynurenic acid or to the neurotoxic agent quinolinic acid. The break-up of these endogenous compounds' balance can be observable in many disorders such as stroke, epilepsy, multiple sclerosis, and amyotrophic lateral sclerosis. It can also occur in neurodegenerative disorders such as Parkinson's disease, Huntington's, and Alzheimer's disease; and in mental disorders such as schizophrenia and depression.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Kynureninase (KYNU) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Mutation (c.468T-A, c.1045_1051delTTTAAGC) of KYNU
                      Induced Change L-Kynurenine concentration: increase (FC = 2.3)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Hereditary methemoglobinemia [ICD-11: 3A92]
                      Details It is reported that mutation (c.468T-A, c.1045_1051delTTTAAGC) of KYNU leads to the increase of L-kynurenine levels compared with control group.
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change L-Kynurenine concentration: decrease (FC = 0.45 / 0.54)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of L-kynurenine levels compared with control group.
      Oxidoreductases (EC 1)
            3-hydroxyanthranilate oxygenase (HAAO) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Mutation (c.483dupT) of HAAO
                      Induced Change L-Kynurenine concentration: increase (FC = 1.33)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Hereditary methemoglobinemia [ICD-11: 3A92]
                      Details It is reported that mutation (c.483dupT) of HAAO leads to the increase of L-kynurenine levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Mutation (c.558G-A) of HAAO
                      Induced Change L-Kynurenine concentration: increase (FC = 1.2)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Hereditary methemoglobinemia [ICD-11: 3A92]
                      Details It is reported that mutation (c.558G-A) of HAAO leads to the increase of L-kynurenine levels compared with control group.
      Transcription factor (TF)
            R2R3-MYB (AN2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Overexpression of AN2
                      Induced Change L-Kynurenine concentration: decrease (FC = 0.38)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of AN2 leads to the decrease of L-kynurenine levels compared with control group.
References
1 NAD Deficiency, Congenital Malformations, and Niacin Supplementation. N Engl J Med. 2017 Aug 10;377(6):544-552.
2 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
3 Comprehensive Influences of Overexpression of a MYB Transcriptor Regulating Anthocyanin Biosynthesis on Transcriptome and Metabolome of Tobacco Leaves. Int J Mol Sci. 2019 Oct 16;20(20):5123.

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