You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00007
NameQuinolinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionQuinolinic acid, also known as quinolinate, 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 is a very strong basic compound (based on its pKa). Quinolinic acid exists in all living species, ranging from bacteria to humans. quinolinic acid and phosphoribosyl pyrophosphate can be converted into nicotinic acid mononucleotide; which is catalyzed by the enzyme nicotinate-nucleotide pyrophosphorylase [carboxylating]. In yeast, quinolinic acid is involved in the metabolic pathway called the nad metabolism pathway.
Structure
Thumb
Synonyms
  • 2,3-pyridinedicarboxylate
  • 2,3-pyridinedicarboxylic acid
  • 3,4-Pyridinedicarboxylic acid
  • Pyridin-2,3-dicarbonsaeure
  • pyridine-2,3-carboxylate
  • Pyridine-2,3-dicarboxylate
  • Pyridine-2,3-dicarboxylic acid
  • Pyridine-3,4-dicarboxylic acid
  • Quinolinate
  • Quinolinic acid
  • Quinolinic acid, copper(2+) salt
  • Quinolinic acid, disodium salt
  • Quinolinic acid, strontium salt
CAS number89-00-9
WeightAverage: 167.1189
Monoisotopic: 167.021857653
InChI KeyGJAWHXHKYYXBSV-UHFFFAOYSA-N
InChIInChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
IUPAC Namepyridine-2,3-dicarboxylic acid
Traditional IUPAC Namequinolinic acid
Chemical FormulaC7H5NO4
SMILES[H]OC(=O)C1=NC([H])=C([H])C([H])=C1C(=O)O[H]
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
Physical Properties
StateSolid
Charge0
Melting point190 °C
Experimental Properties
PropertyValueReference
Water Solubility11 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.07 g/LALOGPS
logP0.15ALOGPS
logP-0.54ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)0.29ChemAxon
pKa (Strongest Basic)5.26ChemAxon
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Nucleus
Organoleptic PropertiesNot Available
SMPDB Pathways
NAD metabolismPW002421 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Nicotinate and nicotinamide metabolismec00760 Map00760
Tryptophan metabolismec00380 Map00380
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
Quinolinic acid + hydron + Phosphoribosyl pyrophosphatePyrophosphate + Carbon dioxide + Nicotinic acid mononucleotide
KEGG Reactions
Quinolinic acid + Phosphoribosyl pyrophosphate + hydronPyrophosphate + Carbon dioxide + Nicotinic acid mononucleotide
Dihydroxyacetone phosphate + Iminoaspartic acidwater + Quinolinic acid + phosphate
2-amino-3-(3-oxoprop-1-enyl)but-2-enedioateQuinolinic acid + water + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Panozzo, C., Nawara, M., Suski, C., Kucharczyka, R., Skoneczny, M., Becam, A. M., Rytka, J., Herbert, C. J. (2002). "Aerobic and anaerobic NAD+ metabolism in Saccharomyces cerevisiae." FEBS Lett 517:97-102.12062417
  • di Luccio, E., Wilson, D. K. (2008). "Comprehensive X-ray structural studies of the quinolinate phosphoribosyl transferase (BNA6) from Saccharomyces cerevisiae." Biochemistry 47:4039-4050.18321072
Synthesis Reference:Akhmerova, 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.
External Links:
ResourceLink
CHEBI ID16675
HMDB IDHMDB00232
Pubchem Compound ID1066
Kegg IDC03722
ChemSpider ID1037
FOODB IDFDB021913
WikipediaQuinolinic_acid
BioCyc IDQUINOLINATE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved in the catabolism of quinolinic acid (QA)
Gene Name:
BNA6
Uniprot ID:
P43619
Molecular weight:
32364.69922
Reactions
Nicotinate D-ribonucleotide + diphosphate + CO(2) → pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1-diphosphate.