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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:27 UTC
HMDB IDHMDB0000881
Secondary Accession Numbers
  • HMDB00881
Metabolite Identification
Common NameXanthurenic acid
DescriptionXanthurenic acid, also known as xanthurenate or 8-hydroxykynurenic acid, is a member of the class of compounds known as quinoline carboxylic acids. Quinoline carboxylic acids are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Xanthurenic acid is slightly soluble (in water). Xanthurenic acid can be found primarily in blood, feces, and urine, as well as in human epidermis tissue. Within the cell, xanthurenic acid is primarily located in the membrane. Xanthurenic acid exists in all eukaryotes, ranging from yeast to humans. In humans, xanthurenic acid is involved in the tryptophan metabolism. Moreover, xanthurenic acid is found to be associated with citrullinemia type I, which is an inborn error of metabolism. Xanthurenic acid is a metabolite from tryptophan catabolism. It is a substrate of the enzyme methyltransferases (EC 2.1.1.-) in pathway tryptophan metabolism (KEGG).
Structure
Data?1582752162
Synonyms
ValueSource
XanthurenateKegg
8-Hydroxykynurenic acidHMDB
Gametocyte activating factor (gaf)HMDB
4,8-Dihydroxy-2-quinolinecarboxylateHMDB
4,8-Dihydroxy-2-quinolinecarboxylic acidHMDB
4,8-Dihydroxy-quinaldateHMDB
4,8-Dihydroxy-quinaldic acidHMDB
4,8-DihydroxyquinaldateHMDB
4,8-Dihydroxyquinaldic acidHMDB
4,8-DihydroxyquinaldinateHMDB
4,8-Dihydroxyquinaldinic acidHMDB
4,8-Dihydroxyquinoline-2-carboxylateHMDB
4,8-Dihydroxyquinoline-2-carboxylic acidHMDB
4-Oxoxanthurenic acidHMDB
8-HydroxykynurenateHMDB
OxoxanthurenateHMDB
XanthurateHMDB
Xanthuric acidHMDB
Chemical FormulaC10H7NO4
Average Molecular Weight205.1669
Monoisotopic Molecular Weight205.037507717
IUPAC Name4,8-dihydroxyquinoline-2-carboxylic acid
Traditional Namexanthurenic acid
CAS Registry Number59-00-7
SMILES
OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1
InChI Identifier
InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)
InChI KeyFBZONXHGGPHHIY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-2-carboxylic acid
  • Dihydroquinolone
  • Hydroxyquinoline
  • 8-hydroxyquinoline
  • Dihydroquinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point289 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.63 g/LALOGPS
logP2.01ALOGPS
logP-0.17ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.14ChemAxon
pKa (Strongest Basic)5.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.65 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity50.83 m³·mol⁻¹ChemAxon
Polarizability19.06 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalMetCCS_train_neg132.51330932474
DeepCCS[M+H]+ExperimentalMetCCS_train_pos140.46930932474
AllCCS[M-H]-ExperimentalNot Available134.1http://allccs.zhulab.cn/database/detail?ID=AllCCS00000333
AllCCS[M+H]+ExperimentalNot Available140.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000333
DarkChem[M+H]+PredictedNot Available145.77231661259
DarkChem[M-H]-PredictedNot Available144.08531661259
AllCCS[M+H]+PredictedNot Available143.63232859911
AllCCS[M-H]-PredictedNot Available140.60732859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Xanthurenic acid,1TMS,#12301.714https://arxiv.org/abs/1905.12712
Xanthurenic acid,1TMS,#22272.1418https://arxiv.org/abs/1905.12712
Xanthurenic acid,1TMS,#32267.1187https://arxiv.org/abs/1905.12712
Xanthurenic acid,2TMS,#12200.93https://arxiv.org/abs/1905.12712
Xanthurenic acid,2TMS,#22220.033https://arxiv.org/abs/1905.12712
Xanthurenic acid,2TMS,#32241.772https://arxiv.org/abs/1905.12712
Xanthurenic acid,3TMS,#12257.7842https://arxiv.org/abs/1905.12712
Xanthurenic acid,1TBDMS,#12558.8623https://arxiv.org/abs/1905.12712
Xanthurenic acid,1TBDMS,#22563.162https://arxiv.org/abs/1905.12712
Xanthurenic acid,1TBDMS,#32533.044https://arxiv.org/abs/1905.12712
Xanthurenic acid,2TBDMS,#12766.957https://arxiv.org/abs/1905.12712
Xanthurenic acid,2TBDMS,#22775.922https://arxiv.org/abs/1905.12712
Xanthurenic acid,2TBDMS,#32804.2644https://arxiv.org/abs/1905.12712
Xanthurenic acid,3TBDMS,#13001.6414https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0563900000-9a574c7d3effa0b192742014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-1563900000-1b0b2fc6caac1ac637a52014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0232900000-540a2f1838749e5da2912017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0563900000-9a574c7d3effa0b192742017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-1563900000-1b0b2fc6caac1ac637a52017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vi-0910000000-eb5f12387da253ffea092016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-5009200000-7ce87a515165642720dd2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0590000000-e130e584059a7dd082262012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-0900000000-bd9a9768f7b716a5eb2b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003r-5900000000-6120cbfe1c7c517939102012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0910000000-15a7a4353f513ac53e482012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0900000000-37c7cba5a7933c2918292012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0900000000-fb1104898a85e262eb322012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-1900000000-aa8f1e95e14bd25bb8c42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-3900000000-693b38057f05e771cc542012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004i-0910000000-1b3d8f0b5d44d2f4f7fb2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTOF , Positivesplash10-001i-0900000000-c536b681ae03102325822017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0390000000-14cea774f303a59fa9052017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-15824b481226de9cecf22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-8f47ef6ebecafe34e3152017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-07w9-0900000000-fbce68ee4689a56033fc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00lr-0900000000-100f6b77c591b26641522017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0910000000-15a7a4353f513ac53e482017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-37c7cba5a7933c2918292017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-fb1104898a85e262eb322017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-aa8f1e95e14bd25bb8c42017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0590000000-726653998e487aeb21972016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0920000000-1851142dfaf7cd6991522016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0900000000-734222988fd38fa8fcf12016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0390000000-ae1209f92413230a3a3c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w29-0960000000-40a305f409d4090926572016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08gl-2900000000-21ba1ed88fab855ade652016-09-12View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 50.32 MHz, DMSO-d6, experimental)2016-09-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.022 +/- 0.001 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0 uMChildren (1 - 13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.28 +/- 0.44 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.0 (0.0 - 4.0) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0550 (0.00400-0.100) umol/mmol creatinineChildren (1 - 13 years old)Not SpecifiedNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified5.537 +/- 6.597 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.10 +/- 0.17 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.17 +/- 0.06 uMAdult (>18 years old)BothHemodialysis details
BloodDetected and Quantified3.0 (2.0 - 4.0) uMChildren (1-13 years old)Not SpecifiedKynureninase deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
UrineDetected and Quantified200.0 (194.0 - 260.0) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedKynureninase deficiency details
UrineDetected and Quantified5.643 +/- 3.642 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Hemodialysis
  1. Pawlak D, Pawlak K, Malyszko J, Mysliwiec M, Buczko W: Accumulation of toxic products degradation of kynurenine in hemodialyzed patients. Int Urol Nephrol. 2001;33(2):399-404. [PubMed:12092667 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Kynureninase deficiency
  1. Christensen M, Duno M, Lund AM, Skovby F, Christensen E: Xanthurenic aciduria due to a mutation in KYNU encoding kynureninase. J Inherit Metab Dis. 2007 Apr;30(2):248-55. Epub 2007 Mar 1. [PubMed:17334708 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022297
KNApSAcK IDNot Available
Chemspider ID5497
KEGG Compound IDC02470
BioCyc IDXANTHURENATE
BiGG IDNot Available
Wikipedia LinkXanthurenic_acid
METLIN ID5841
PubChem Compound5699
PDB IDNot Available
ChEBI ID10072
Food Biomarker OntologyNot Available
VMH IDC02470
MarkerDB IDMDB00000273
References
Synthesis ReferenceFurst, Arthur; Olsen, Carl J. A convenient synthesis of xanthurenic acid. Journal of Organic Chemistry (1951), 16 412-14.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bapurao S, Krishnaswamy K: Vitamin B6 nutritional status of pellagrins and their leucine tolerance. Am J Clin Nutr. 1978 May;31(5):819-24. [PubMed:206127 ]
  2. Shibata K, Fukuwatari T, Murakami M, Sasaki R: Increase in conversion of tryptophan to niacin in pregnant rats. Adv Exp Med Biol. 2003;527:435-41. [PubMed:15206761 ]
  3. Forrest CM, Gould SR, Darlington LG, Stone TW: Levels of purine, kynurenine and lipid peroxidation products in patients with inflammatory bowel disease. Adv Exp Med Biol. 2003;527:395-400. [PubMed:15206756 ]
  4. Calandra P: Research on tryptophan metabolites "via kynurenine" in epidermis of man and mouse. Acta Vitaminol Enzymol. 1975;29(1-6):158-60. [PubMed:1244085 ]
  5. Hoes MJ, Loeffen T, Vree TB: Kinetics of L-tryptophan in depressive patients: a possible correlation between the plasma concentrations of L-tryptophan and some psychiatric rating scales. Psychopharmacology (Berl). 1981;75(4):350-3. [PubMed:6803278 ]
  6. Malina HZ, Hess OM: Xanthurenic acid translocates proapoptotic Bcl-2 family proteins into mitochondria and impairs mitochondrial function. BMC Cell Biol. 2004 Apr 6;5:14. [PubMed:15068490 ]
  7. Bapurao S, Raman L, Tulpule PG: Biochemical assessment of vitamin B6 nutritional status in pregnant women with orolingual manifestations. Am J Clin Nutr. 1982 Oct;36(4):581-6. [PubMed:7124659 ]
  8. Malina HZ: Comment on 'The photosensitiser xanthurenic acid is not present in normal human lenses' by P.G. Hains et al. [Exp. Eye Res. 77 (2003) 547-553]. Exp Eye Res. 2004 Sep;79(3):443-5; author reply 447-8. [PubMed:15336509 ]
  9. Forrest CM, Kennedy A, Stone TW, Stoy N, Darlington LG: Kynurenine and neopterin levels in patients with rheumatoid arthritis and osteoporosis during drug treatment. Adv Exp Med Biol. 2003;527:287-95. [PubMed:15206742 ]
  10. Igari T, Tsuchizawa M, Shimamura T: Alteration of tryptophan metabolism in the synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Tohoku J Exp Med. 1987 Oct;153(2):79-86. [PubMed:3500530 ]

Enzymes

General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Molecular weight:
Not Available
Reactions
Xanthurenic acid + S-Adenosylmethionine → 8-Methoxykynurenate + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available
Reactions
Xanthurenic acid + S-Adenosylmethionine → 8-Methoxykynurenate + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Molecular weight:
Not Available
Reactions
Xanthurenic acid + S-Adenosylmethionine → 8-Methoxykynurenate + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.
Gene Name:
WBSCR22
Uniprot ID:
O43709
Molecular weight:
Not Available
Reactions
Xanthurenic acid + S-Adenosylmethionine → 8-Methoxykynurenate + S-Adenosylhomocysteinedetails