Record Information
Version1.0
Creation date2011-09-21 00:11:43 UTC
Update date2015-10-09 22:27:28 UTC
Primary IDFDB022297
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthurenic acid
DescriptionXanthurenic acid, also known as xanthurenate or 8-hydroxykynurenate, 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. Xanthurenic acid is a very strong basic compound (based on its pKa). Xanthurenic acid exists in all living species, ranging from bacteria to humans. Xanthurenic acid, with regard to humans, has been found to be associated with several diseases such as hemodialysis, eosinophilic esophagitis, and colorectal cancer; xanthurenic acid has also been linked to the inborn metabolic disorder kynureninase deficiency.
CAS Number59-00-7
Structure
Thumb
Synonyms
SynonymSource
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
4-oxoxanthurenic acidhmdb
4,8-dihydroxy-Quinaldatehmdb
4,8-dihydroxy-Quinaldic acidhmdb
oxoxanthurenatehmdb
Predicted 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
Chemical FormulaC10H7NO4
IUPAC name4,8-dihydroxyquinoline-2-carboxylic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1
Average Molecular Weight205.1669
Monoisotopic Molecular Weight205.037507717
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSXanthurenic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0563900000-9a574c7d3effa0b19274Spectrum
GC-MSXanthurenic acid, 3 TMS, GC-MS Spectrumsplash10-0a4i-1563900000-1b0b2fc6caac1ac637a5Spectrum
GC-MSXanthurenic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0232900000-540a2f1838749e5da291Spectrum
GC-MSXanthurenic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0563900000-9a574c7d3effa0b19274Spectrum
GC-MSXanthurenic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-1563900000-1b0b2fc6caac1ac637a5Spectrum
Predicted GC-MSXanthurenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06vi-0910000000-eb5f12387da253ffea09Spectrum
Predicted GC-MSXanthurenic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-5009200000-7ce87a515165642720ddSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0590000000-e130e584059a7dd08226Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a59-0900000000-bd9a9768f7b716a5eb2bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003r-5900000000-6120cbfe1c7c51793910Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0910000000-15a7a4353f513ac53e48Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0900000000-37c7cba5a7933c291829Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0900000000-fb1104898a85e262eb32Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-1900000000-aa8f1e95e14bd25bb8c4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-3900000000-693b38057f05e771cc54Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004i-0910000000-1b3d8f0b5d44d2f4f7fbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTOF , Positivesplash10-001i-0900000000-c536b681ae0310232582Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0390000000-14cea774f303a59fa905Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-15824b481226de9cecf2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-8f47ef6ebecafe34e315Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-07w9-0900000000-fbce68ee4689a56033fcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00lr-0900000000-100f6b77c591b2664152Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0910000000-15a7a4353f513ac53e48Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-37c7cba5a7933c291829Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-fb1104898a85e262eb32Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-aa8f1e95e14bd25bb8c4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0590000000-726653998e487aeb2197Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0920000000-1851142dfaf7cd699152Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0900000000-734222988fd38fa8fcf1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0390000000-ae1209f92413230a3a3cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w29-0960000000-40a305f409d409092657Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08gl-2900000000-21ba1ed88fab855ade65Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID5497
ChEMBL IDCHEMBL312535
KEGG Compound IDC02470
Pubchem Compound ID5699
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00881
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDXanthurenic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference