Page last updated: 2024-12-04

3-hydroxykynurenine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

3-hydroxykynurenine: RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3-hydroxykynurenine : A hydroxykynurenine that is kynurenine substituted by a hydroxy group at position 3. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

hydroxykynurenine : A hydroxy-amino acid that is kynurenine substituted by a single hydroxy group at unspecified position. A "closed" class. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID89
CHEMBL ID442576
CHEBI ID1547
SCHEMBL ID180582
MeSH IDM0046332

Synonyms (60)

Synonym
2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
CHEBI:1547 ,
3-(2-amino-3-hydroxybenzoyl)alanine
SMP1_000159
benzenebutanoic acid, alpha,2-diamino-3-hydroxy-gamma-oxo-
ccris 4426
nsc 96400
kynurenine, 3-hydroxy (r,s)
PRESTWICK_659
NCGC00179533-01
kynurenine, 3-hydroxy-
3-(3-hydroxyanthraniloyl)alanine
benzenebutanoic acid,2-diamino-3-hydroxy-.gamma.-oxo-
wln: zr bq fv1yzvq
nsc96400
484-78-6
nsc-96400
hydroxykynurenine
alanine, 3-(3-hydroxyanthraniloyl)-
BPBIO1_000576
BCBCMAP01_000037
BSPBIO_000522
C02794
3-hydroxykynurenine
2147-61-7
3-hydroxy-dl-kynurenine
PRESTWICK2_000451
SPBIO_002461
PRESTWICK1_000451
PRESTWICK0_000451
PRESTWICK3_000451
dl-3-hydroxykynurenine
3-(3-hydroxyanthraniloyl)-alanine
HMS1569K04
CHEMBL442576
2-amino-4-(2-amino-3-hydroxy-phenyl)-4-oxo-butanoic acid; 2-amino-4-(2-amino-3-hydroxy-phenyl)-4-keto-butyric acid; (+-)-alpha,2-diamino-3-hydroxy-gamma-oxobenzenebutanoic acid
A840809
2-azanyl-4-(2-azanyl-3-oxidanyl-phenyl)-4-oxidanylidene-butanoic acid
A815406
AKOS016004491
unii-27723548jl
27723548jl ,
FT-0634065
SCHEMBL180582
dl-3-hydroxykyunrenine
VCKPUUFAIGNJHC-UHFFFAOYSA-N
.alpha.,2-diamino-3-hydroxy-.gamma.-oxobenzenebutanoic acid
mfcd00047832
benzenebutanoic acid, .alpha.,2-diamino-3-hydroxy-.gamma.-oxo-
2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoicacid
J-014094
oh-kynurenine
hydroxykinurenine
Q2815992
DTXSID00862009
MS-23258
HY-113294
alpha,2-diamino-3-hydroxy-gamma-oxobenzenebutanoic acid
CS-0059538
EX-A7998H

Research Excerpts

Overview

3-Hydroxykynurenine (3-HK) is a tryptophan metabolite with an o-aminophenol structure. 3-HK is a potential neurotoxin whose increased levels have been described in several neurodegenerative disorders.

ExcerptReferenceRelevance
"3-Hydroxykynurenine is a tryptophan metabolite with an o-aminophenol structure. "( 3-hydroxykynurenine as a substrate/activator for mushroom tyrosinase.
Cecchini, G; Curreli, N; Rescigno, A; Sanjust, E; Sollai, F, 2003
)
3.2
"3-Hydroxykynurenine (3-HK), which is an endogenous metabolite of tryptophan in the kynurenine pathway, is a potential neurotoxin in several neurodegenerative disorders. "( Epigallocatechin 3-gallate attenuates neuronal damage induced by 3-hydroxykynurenine.
Choi, BS; Jeong, JH; Kim, HJ; Kim, MK; Lee, TJ; Park, ES, 2004
)
2
"3-Hydroxykynurenine (3-HK) is a tryptophan metabolite whose level in the brain is elevated under several pathological states including Huntington's disease. "( 3-Hydroxykynurenine toxicity on the rat striatum in vivo.
Katsuki, H; Nakagami, Y; Saito, H, 1996
)
3.18
"3-Hydroxykynurenine (3-HK) is a tryptophan metabolite whose level in the brain is markedly elevated under several pathological conditions, including Huntington disease and human immunodeficiency virus infection. "( Hydrogen peroxide-mediated neuronal cell death induced by an endogenous neurotoxin, 3-hydroxykynurenine.
Katsuki, H; Nishiyama, N; Okuda, S; Saito, H, 1996
)
1.96
"3-Hydroxykynurenine (3-HK) is a potential endogenous neurotoxin whose increased levels have been described in several neurodegenerative disorders. "( 3-Hydroxykynurenine, an endogenous oxidative stress generator, causes neuronal cell death with apoptotic features and region selectivity.
Katsuki, H; Nishiyama, N; Okuda, S; Saito, H, 1998
)
3.19
"3-Hydroxykynurenine (3-OHKyn) is a tryptophan metabolite that is readily autoxidised to products that may be involved in protein modification and cytotoxicity. "( Characterisation of the major autoxidation products of 3-hydroxykynurenine under physiological conditions.
Garner, B; Sheil, MM; Truscott, RJ; Vazquez, S, 2000
)
2

Effects

ExcerptReferenceRelevance
"3-Hydroxykynurenine has been largely described as one of these toxic metabolites capable of inducing oxidative damage and cell death; consequently, this metabolite has been hypothesized to play a pivotal role in different neurological and psychiatric disorders."( 3-Hydroxykynurenine: an intriguing molecule exerting dual actions in the central nervous system.
Colín-González, AL; Maldonado, PD; Santamaría, A, 2013
)
2.55

Toxicity

ExcerptReferenceRelevance
" These data suggest a direct role for H2O2 and metal ions in the cytotoxic action of 3HK and indicate that cell lysis results from the intracellular accumulation of toxic levels of H2O2."( The role of hydrogen peroxide in the in vitro cytotoxicity of 3-hydroxykynurenine.
Eastman, CL; Guilarte, TR, 1990
)
0.52
"The adverse effects of D-tryptophan and the possibility of it being a surrogate index for predicting adverse effects in rats were investigated."( The urinary ratio of 3-hydroxykynurenine/3-hydroxyanthranilic acid is an index to predicting the adverse effects of D-tryptophan in rats.
Fukuwatari, T; Ohno, T; Sano, M; Shibata, K, 2014
)
0.72

Bioavailability

ExcerptReferenceRelevance
"Boosting KYNA levels, through interference with the KP enzymes or through application of prodrugs/analogs with high bioavailability and potency, is a promising clinical approach."( Kynurenic acid in neurodegenerative disorders-unique neuroprotection or double-edged sword?
Ostapiuk, A; Urbanska, EM, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" The blue fluorophore was formed first and appeared then to be photochemically converted to the green one, with the rate of formation of the latter increasing with an increase in UV dosage or oxidizing conditions."( Model studies on the photochemical production of lenticular fluorophores.
Dillon, J; Ellozy, AR; Wang, RH, 1994
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
hydroxykynurenineA hydroxy-amino acid that is kynurenine substituted by a single hydroxy group at unspecified position. A "closed" class.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (3)

PathwayProteinsCompounds
Kynurenine pathway and links to cell senescence2024
NAD biosynthesis II (from tryptophan)024
Selenium micronutrient network095

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
tryptophan catabolic processKynureninaseHomo sapiens (human)
NAD biosynthetic processKynureninaseHomo sapiens (human)
quinolinate biosynthetic processKynureninaseHomo sapiens (human)
response to type II interferonKynureninaseHomo sapiens (human)
'de novo' NAD biosynthetic process from tryptophanKynureninaseHomo sapiens (human)
response to vitamin B6KynureninaseHomo sapiens (human)
anthranilate metabolic processKynureninaseHomo sapiens (human)
L-kynurenine catabolic processKynureninaseHomo sapiens (human)
tryptophan catabolic process to kynurenineKynureninaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
pyridoxal phosphate bindingKynureninaseHomo sapiens (human)
kynureninase activityKynureninaseHomo sapiens (human)
protein homodimerization activityKynureninaseHomo sapiens (human)
3-hydroxykynureninase activityKynureninaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleoplasmKynureninaseHomo sapiens (human)
mitochondrionKynureninaseHomo sapiens (human)
cytosolKynureninaseHomo sapiens (human)
cytoplasmKynureninaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID412645Ratio of kcat to Km for human kynureninase N333T mutant2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.
AID412641Activity of human kynureninase S332G/N333T mutant2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.
AID412647Ratio of kcat to Km for human kynureninase H102W/N333T mutant2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.
AID412640Activity of human kynureninase N333T mutant2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.
AID412648Ratio of kcat to Km for human kynureninase H102W/S332G/N333T mutant2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.
AID412637Activity of human wild type kynureninase2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.
AID412646Ratio of kcat to Km for human kynureninase S332G/N333T mutant2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.
AID412644Ratio of kcat to Km for human wild type kynureninase2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (302)

TimeframeStudies, This Drug (%)All Drugs %
pre-199044 (14.57)18.7374
1990's70 (23.18)18.2507
2000's65 (21.52)29.6817
2010's108 (35.76)24.3611
2020's15 (4.97)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.07

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index32.07 (24.57)
Research Supply Index5.77 (2.92)
Research Growth Index4.76 (4.65)
Search Engine Demand Index42.88 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (1.91%)5.53%
Reviews9 (2.87%)6.00%
Case Studies3 (0.96%)4.05%
Observational1 (0.32%)0.25%
Other295 (93.95%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]