Showing metabocard for Kynurenic acid (BMDB0000715)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:22 UTC
Update Date2020-05-11 20:47:52 UTC
BMDB IDBMDB0000715
Secondary Accession Numbers
  • BMDB00715
Metabolite Identification
Common NameKynurenic acid
DescriptionKynurenic acid, also known as kynurenic acid or kynurenic acid, 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. Kynurenic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Kynurenic acid exists in all eukaryotes, ranging from yeast to humans. In cattle, kynurenic acid is involved in the metabolic pathway called the tryptophan metabolism pathway. Kynurenic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Hydroxy-2-chinolincarbonsaeureChEBI
4-Hydroxy-2-quinolinecarboxylic acidChEBI
4-Hydroxyquinaldic acidChEBI
4-Hydroxyquinaldinic acidChEBI
KynurenateChEBI
KynurensaeureChEBI
4-Hydroxy-2-quinolinecarboxylateGenerator
4-HydroxyquinaldateGenerator
4-HydroxyquinaldinateGenerator
2-Carboxy-4-hydroxyquinolineHMDB
4-Hydroxy-quinaldateHMDB
4-Hydroxy-quinaldic acidHMDB
4-Hydroxyquinoline-2-carboxylateHMDB
4-Hydroxyquinoline-2-carboxylic acidHMDB
Quinurenic acidHMDB
Acid, kynurenicMeSH, HMDB
Chemical FormulaC10H7NO3
Average Molecular Weight189.1675
Monoisotopic Molecular Weight189.042593095
IUPAC Name4-oxo-1,4-dihydroquinoline-2-carboxylic acid
Traditional Nameacid, kynurenic
CAS Registry Number492-27-3
SMILES
OC(=O)C1=CC(=O)C2=CC=CC=C2N1
InChI Identifier
InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)
InChI KeyHCZHHEIFKROPDY-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
  • Dihydroquinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point280 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.16ALOGPS
logP1.58ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity52.32 m³·mol⁻¹ChemAxon
Polarizability18.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Brain
  • Epidermis
  • Fibroblasts
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000715
DrugBank IDDB11937
Phenol Explorer Compound IDNot Available
FooDB IDFDB022200
KNApSAcK IDC00026453
Chemspider ID3712
KEGG Compound IDC01717
BioCyc IDKYNURENATE
BiGG ID38234
Wikipedia LinkKynurenic_acid
METLIN ID5683
PubChem Compound3845
PDB IDNot Available
ChEBI ID18344
References
Synthesis ReferenceStone, T. W. Development and therapeutic potential of kynurenic acid and kynurenine derivatives for neuroprotection. Trends in Pharmacological Sciences (2000), 21(4), 149-154.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available