Page last updated: 2024-12-05

xanthurenic acid

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

Description

xanthurenic acid : A quinolinemonocarboxylic acid that is quinoline-2-carboxylic acid substituted by hydroxy groups at C-4 and C-8. [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 CID5699
CHEMBL ID312535
CHEBI ID10072
SCHEMBL ID379760
MeSH IDM0091306

Synonyms (99)

Synonym
4,8-dihydroxyquinoline-2-carboxylic
BIDD:GT0640
brn 0185954
einecs 200-410-1
quinaldic acid, 4,8-dihydroxy-
ccris 4429
c10h7no4
nsc 401570
CHEMBL312535 ,
chebi:10072 ,
KBIO1_000262
DIVK1C_000262
SDCCGMLS-0066616.P001
SPECTRUM_000253
OPREA1_107134
BSPBIO_001846
IDI1_000262
SPECTRUM5_001562
wln: t66 bnj cvq eq jq
4,8-dihydroxy-2-quinolinecarboxylic acid
4,8-dihydroxyquinaldic acid
2-quinolinecarboxylic acid,8-dihydroxy-
nsc-401570
quinaldic acid,8-dihydroxy-
C02470
59-00-7
xanthurenic acid
xanthurenate ,
xanthuric acid
NSC401570 ,
4,8-dihydroxyquinaldinic acid
4,8-dihydroxyquinoline-2-carboxylic acid
8-hydroxykynurenic acid
2-quinolinecarboxylic acid, 4,8-dihydroxy-
xanthurenic acid, 96%
CU-01000012491-3
NCGC00094846-02
NCGC00094846-01
NCGC00094846-04
KBIOGR_000474
KBIO3_001046
KBIOSS_000733
KBIO2_003301
KBIO2_000733
KBIO2_005869
SPECTRUM4_000117
NINDS_000262
SPECTRUM3_000143
SPBIO_000296
SPECTRUM2_000158
SPECTRUM1500754
NCGC00094846-03
NCGC00094846-05
X-1500
B5FF212D-76CB-4875-8A36-C67D8E69489C
quinoline-2-carboxylic acid, 4,8-dihydroxy-
HMS500N04
4,8-dihydroxy-quinoline-2-carboxylic acid anion
4,8-dihydroxy-quinoline-2-carboxylic acid(xanthurenate)
bdbm50113313
X0054
HMS1921G08
8-hydroxy-4-oxo-1h-quinoline-2-carboxylic acid
AKOS003237896
A832107
CCG-38363
unii-58lab1bg8j
58lab1bg8j ,
BP-10912
FT-0631263
AM20061355
AKOS015894330
S4774
xanthurenic acid [mi]
mfcd00006754
SCHEMBL379760
HB0659
4kl ,
DTXSID90207728
sr-05000002445
SR-05000002445-1
xanthurate
8-hydroxykynurenate
4,8-dihydroxyquinaldate
4,8-dihydroxy-quinaldate
4,8-dihydroxy-quinaldic acid
oxoxanthurenate
4,8-dihydroxy-2-quinolinecarboxylate
4,8-dihydroxyquinaldinate
4-oxoxanthurenic acid
HY-W014666
CS-W015382
xanthurenate; 8-hydroxykynurenic acid; 4,8-dihydroxyquinaldic acid
Q5961262
4,8-dihydroxyquinolinium-2-carboxylate
BRD-K07327532-001-03-6
HMS3885N22
AS-56782
SB72014

Research Excerpts

Overview

Xanthurenic acid (XA) is a metabolite of the tryptophan oxidation pathway through kynurenine and 3-hydroxykynuranine. It is an endogenous molecule leading to caspase-9 and -3 activation.

ExcerptReferenceRelevance
"Xanthurenic acid (XA) is a known endogenous molt regulator present in arthropods."( Elucidating a chemical defense mechanism of Antarctic sponges: A computational study.
Baker, BJ; Kearns, FL; Larkin, JD; Lee Woodcock, H; Vankayala, SL, 2017
)
1.18
"Xanthurenic acid (XA) is a metabolite of the tryptophan oxidation pathway through kynurenine and 3-hydroxykynurenine. "( Xanthurenic acid binds to neuronal G-protein-coupled receptors that secondarily activate cationic channels in the cell line NCB-20.
Bourguignon, JJ; Brumaru, D; Kemmel, V; Klein, C; Maammar, M; Maitre, M; Mensah-Nyagan, AG; Schmitt, M; Taleb, O, 2012
)
3.26
"Xanthurenic acid is an endogenous molecule leading to caspase-9 and -3 activation. "( Abnormal signalling of 14-3-3 proteins in cells with accumulated xanthurenic acid.
Frueh, BE; Malina, HZ, 2003
)
2
"Xanthurenic acid is an endogenous molecule produced by tryptophan degradation, produced in the cytoplasm and mitochondria. "( Xanthurenic acid translocates proapoptotic Bcl-2 family proteins into mitochondria and impairs mitochondrial function.
Hess, OM; Malina, HZ, 2004
)
3.21
"Xanthurenic acid is a metabolite of L-tryptophanicotinic acid ribonucleotide biosynthesis. "( The clinical significance of disordered renal excretion of xanthurenic acid in depressive patients.
Hoes, MJ; Sijben, N, 1981
)
1.95
"Xanthurenic acid is an endogenous product of tryptophan degradation by indoleamine 2,3-dioxygenase (IDO). "( Lens epithelial cell apoptosis and intracellular Ca2+ increase in the presence of xanthurenic acid.
Frueh, B; Hess, OM; Malina, H; Richter, C, 2002
)
1.98

Effects

Xanthurenic acid (Xa) has been generally considered as a substance with no physiological role but possessing toxic and apoptotic properties. XA has been implicated as an inducer in vivo of exflagellation in Plasmodium spp.

ExcerptReferenceRelevance
"Xanthurenic acid has potential implications in the pathophysiology of schizophrenia and is a promising candidate as a peripheral biomarker of the disorder."( Cinnabarinic acid and xanthurenic acid: Two kynurenine metabolites that interact with metabotropic glutamate receptors.
Battaglia, G; Bruno, V; Copeland, CS; Curto, M; Fazio, F; Iacovelli, L; Lionetto, L; Neale, SA; Nicoletti, F; Salt, TE, 2017
)
1.49
"Xanthurenic acid (XA) has been implicated as an inducer in vivo of exflagellation in Plasmodium spp. "( Plasmodium development in white-eye (kh(w)) and transformed strains (kh43) of Aedes aegypti (Diptera: Culicidae).
Beerntsen, BT; Li, J, 2006
)
1.78
"Xanthurenic acid (Xa) has been generally considered as a substance with no physiological role but possessing toxic and apoptotic properties."( Xanthurenic acid distribution, transport, accumulation and release in the rat brain.
Aunis, D; Brumaru, D; Dugave, C; Gobaille, S; Kemmel, V; Maitre, M, 2008
)
2.51
"Xanthurenic acid (XA) has been quantified in the serum of normal and vitamin B6-deficient rabbits using high performance liquid chromatography. "( Quantitation of xanthurenic acid in rabbit serum using high performance liquid chromatography.
Boots, LR; Cornwell, PE; Monti, JA; Williams, SA, 1984
)
2.06

Compound-Compound Interactions

ExcerptReferenceRelevance
" Moreover, more information can be provided on the evaluation of toxicity of phorate using metabonomics combined with clinical chemistry."( Metabonomics evaluation of urine from rats administered with phorate under long-term and low-level exposure by ultra-performance liquid chromatography-mass spectrometry.
Guo, L; Hou, Y; Sun, C; Sun, X; Xu, W; Zeng, Y; Zhao, X, 2014
)
0.4

Bioavailability

ExcerptReferenceRelevance
" On the contrary, PN-beta-Glc poorly served as vitamin B6 source, because average bioavailability was only about 22% in comparison to that of PN (100%)."( Feeding experiments of pyridoxine derivatives as vitamin B6.
Hayakawa, T; Maeno, M; Morimoto, Y; Suzuki, Y; Tsuge, H, 1997
)
0.3

Dosage Studied

ExcerptRelevanceReference
" In rats there is no ratio between the dosage used and the levels of the metabolites excreted."( Effects of two different loading doses of L-tryptophan on the urinary excretion of tryptophan metabolites in rats, mice and guinea pigs. Correlation with the enzyme activities.
Allegri, G; Baccichetti, F; Biasiolo, M; Costa, C,
)
0.13
" The significance of several differential metabolites as potential biomarkers of colon inflammation was evaluated in an experiment which compared metabolite concentrations in IL10(-/-) and WT mice housed, either under conventional conditions and dosed with intestinal microflora, or maintained under specific pathogen-free (SPF) conditions."( Identification of urinary biomarkers of colon inflammation in IL10-/- mice using Short-Column LCMS metabolomics.
Cao, M; Edmunds, S; Fraser, K; Lane, G; Lin, HM; Otter, D; Rowan, D, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
metabotropic glutamate receptor agonistAn agonist that selectively binds to and activates a metabotropic glutamate receptor.
iron chelatornull
vesicular glutamate transport inhibitorAn inhibitor that interferes with vesicular glutamate transport.
animal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
[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 (2)

ClassDescription
quinolinemonocarboxylic acidAny aromatic carboxylic acid that contains a quinoline moiety that is substituted by one carboxy substituent.
dihydroxyquinolineAny hydroxyquinoline in which the number of hydroxy substituents is specified as two.
[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
Tryptophan Metabolism1855
Kynurenine pathway and links to cell senescence2024
Biochemical pathways: part I0466
Tryptophan metabolism2342

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency12.58930.004023.8416100.0000AID485290
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency9.97630.140911.194039.8107AID2451
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency28.18380.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency13.89140.177814.390939.8107AID2147
phosphopantetheinyl transferaseBacillus subtilisPotency79.43280.141337.9142100.0000AID1490
chromobox protein homolog 1Homo sapiens (human)Potency100.00000.006026.168889.1251AID540317
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Vesicular glutamate transporter 3Rattus norvegicus (Norway rat)Ki190.00000.04000.11500.1900AID216240
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID643060Inhibition of human plasma lipoprotein-associated phospholipase A2 using 2-thio-PAF as substrate preincubated for 20 mins measured 1 hr post substrate addition by spectrophotometric analysis in presence of EDTA2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Amides of xanthurenic acid as zinc-dependent inhibitors of Lp-PLA(2).
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1133374Antiallergic activity in iv dosed Sprague-Dawley rat assessed as inhibition of egg albumin-induced passive cutaneous anaphylaxis1978Journal of medicinal chemistry, Sep, Volume: 21, Issue:9
Structure-activity correlations for a series of antiallergy agents. Oxanilic, quinaldic, and benzopyran-2-carboxylic acids.
AID1563132Inhibition of TNAS binding to human sepiapterin reductase at 25 uM by 19F-NMR spectra analysis relative to control2019Journal of medicinal chemistry, 07-11, Volume: 62, Issue:13
Fragment-Based Discovery of Novel Potent Sepiapterin Reductase Inhibitors.
AID643059Inhibition of human plasma lipoprotein-associated phospholipase A2 using 2-thio-PAF as substrate preincubated for 20 mins measured 1 hr post substrate addition by spectrophotometric analysis2012Bioorganic & medicinal chemistry letters, Jan-15, Volume: 22, Issue:2
Amides of xanthurenic acid as zinc-dependent inhibitors of Lp-PLA(2).
AID74835Inhibitory activity against vesicular glutamate transport (GVT) in synaptic vesicles isolated from rat forebrain1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Quinoline-2,4-dicarboxylic acids: synthesis and evaluation as inhibitors of the glutamate vesicular transport system.
AID216240Evaluated for competitive inhibition against Vesicular glutamate transporter (VGLUT), and Ki value was reported.2002Journal of medicinal chemistry, May-23, Volume: 45, Issue:11
Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
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.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (278)

TimeframeStudies, This Drug (%)All Drugs %
pre-199093 (33.45)18.7374
1990's42 (15.11)18.2507
2000's50 (17.99)29.6817
2010's78 (28.06)24.3611
2020's15 (5.40)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 44.02

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index44.02 (24.57)
Research Supply Index5.71 (2.92)
Research Growth Index4.63 (4.65)
Search Engine Demand Index67.41 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (44.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (1.69%)5.53%
Reviews8 (2.71%)6.00%
Case Studies4 (1.36%)4.05%
Observational2 (0.68%)0.25%
Other276 (93.56%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]