Showing metabocard for Quinolinic acid (BMDB0000232)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:08 UTC
Update Date2020-05-19 22:01:30 UTC
BMDB IDBMDB0000232
Secondary Accession Numbers
  • BMDB00232
Metabolite Identification
Common NameQuinolinic acid
DescriptionQuinolinic acid, also known as quinolinic acid, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Quinolinic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Quinolinic acid exists in all living species, ranging from bacteria to humans. Quinolinic acid and phosphoribosyl pyrophosphate can be biosynthesized from nicotinic acid mononucleotide through the action of the enzyme nicotinate-nucleotide pyrophosphorylase [carboxylating]. In cattle, quinolinic acid is involved in a couple of metabolic pathways, which include the tryptophan metabolism pathway and the nicotinate and nicotinamide metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3-Pyridinedicarboxylic acidChEBI
Pyridine-2,3-dicarboxylateChEBI
2,3-PyridinedicarboxylateGenerator
QuinolinateGenerator
Pyridine-2,3-dicarboxylic acidGenerator
3,4-Pyridinedicarboxylic acidHMDB
Pyridin-2,3-dicarbonsaeureHMDB
Pyridine-2,3-carboxylateHMDB
Quinolinic acidHMDB
Chemical FormulaC7H5NO4
Average Molecular Weight167.1189
Monoisotopic Molecular Weight167.021857653
IUPAC Namepyridine-2,3-dicarboxylic acid
Traditional Namequinolinic acid
CAS Registry Number89-00-9
SMILES
OC(=O)C1=CC=CN=C1C(O)=O
InChI Identifier
InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
InChI KeyGJAWHXHKYYXBSV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids
Alternative Parents
Substituents
  • Pyridine carboxylic acid
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point190 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.15ALOGPS
logP-1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.31ChemAxon
pKa (Strongest Basic)5.74ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.49 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.04 m³·mol⁻¹ChemAxon
Polarizability14.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Brain
  • Neuron
  • Placenta
  • Prostate Tissue
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
NeuronExpected 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
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000232
DrugBank IDDB01796
Phenol Explorer Compound IDNot Available
FooDB IDFDB031142
KNApSAcK IDC00007381
Chemspider ID144985
KEGG Compound IDC03722
BioCyc IDQUINOLINATE
BiGG IDNot Available
Wikipedia LinkQuinolinic_acid
METLIN IDNot Available
PubChem Compound1066
PDB IDNot Available
ChEBI ID16675
References
Synthesis ReferenceAkhmerova, S. G.; Islamgulova, V. R.; Koksharov, V. G.; Sapozhnikov, Yu. E.; Manaeva, R. M. Methods of preparation of quinolinic acid. Bashkirskii Khimicheskii Zhurnal (2001), 8(2), 9-14.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Nicotinate-nucleotide pyrophosphorylase [carboxylating]
General function:
Coenzyme transport and metabolism
Specific function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
QPRT
Uniprot ID:
Q3T063
Molecular weight:
31151.0
Reactions
Nicotinic acid mononucleotide + Pyrophosphate + Carbon dioxide → Quinolinic acid + Phosphoribosyl pyrophosphatedetails