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Quinolinic acid (YMDB00007)

Identification
YMDB IDYMDB00007
NameQuinolinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionQuinolinic acid is a dicarboxylic acid. It is formed from the metabolism of tryptophan in the kynurenine pathway. Quinolinic acid is used in the formation of NAD.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 pyrophosphate → Pyrophosphate + Carbon dioxide + Nicotinic acid mononucleotide
KEGG Reactions
Quinolinic acid + Phosphoribosyl pyrophosphate + hydron → Pyrophosphate + Carbon dioxide + Nicotinic acid mononucleotide
Dihydroxyacetone phosphate + Iminoaspartic acid → water + Quinolinic acid + phosphate
2-amino-3-(3-oxoprop-1-enyl)but-2-enedioate → Quinolinic 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 IDFDB031142
WikipediaQuinolinic_acid
BioCyc IDQUINOLINATE

Enzymes

Protein Details
1. Nicotinate-nucleotide pyrophosphorylase [carboxylating]
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.