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Identification
NameQuinolinic Acid
Accession NumberDB01796  (EXPT02391)
TypeSmall Molecule
GroupsExperimental
DescriptionA metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIF6F0HK1URN
CAS number89-00-9
WeightAverage: 167.1189
Monoisotopic: 167.021857653
Chemical FormulaC7H5NO4
InChI KeyGJAWHXHKYYXBSV-UHFFFAOYSA-N
InChI
InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
IUPAC Name
pyridine-2,3-dicarboxylic acid
SMILES
OC(=O)C1=CC=CN=C1C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Nicotinate-nucleotide pyrophosphorylase [carboxylating]ProteinunknownNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)P30012 details
Nicotinate-nucleotide pyrophosphorylase [carboxylating]ProteinunknownNot AvailableMycobacterium tuberculosisO06594 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Tryptophan MetabolismMetabolicSMP00063
Nicotinate and Nicotinamide MetabolismMetabolicSMP00048
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis Reference

Robert W. J. Rebhahn, James E. Kassner, Raymond E. Werner, “Process for preparing quinolinic acid.” U.S. Patent US4537971, issued March, 1945.

US4537971
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.823
Blood Brain Barrier+0.7119
Caco-2 permeable+0.5533
P-glycoprotein substrateNon-substrate0.7874
P-glycoprotein inhibitor INon-inhibitor0.9823
P-glycoprotein inhibitor IINon-inhibitor0.9947
Renal organic cation transporterNon-inhibitor0.9413
CYP450 2C9 substrateNon-substrate0.8066
CYP450 2D6 substrateNon-substrate0.8884
CYP450 3A4 substrateNon-substrate0.8135
CYP450 1A2 substrateNon-inhibitor0.9757
CYP450 2C9 inhibitorNon-inhibitor0.9556
CYP450 2D6 inhibitorNon-inhibitor0.9578
CYP450 2C19 inhibitorNon-inhibitor0.9672
CYP450 3A4 inhibitorNon-inhibitor0.9822
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9921
Ames testNon AMES toxic0.9796
CarcinogenicityNon-carcinogens0.9191
BiodegradationReady biodegradable0.7561
Rat acute toxicity2.4057 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9853
hERG inhibition (predictor II)Non-inhibitor0.9815
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point228.5 °CPhysProp
water solubility1.1E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
pKa2.43PERRIN,DD (1972)
Predicted Properties
PropertyValueSource
Water Solubility4.07 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.04 m3·mol-1ChemAxon
Polarizability14.34 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-0910000000-a8eacf1916c539d286b6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0910000000-64e9e4b901dd69dc90c5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-7910000000-0bb1a7ce8a5907feae21View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-4a6d37bd8578b50cf677View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-45dc448cbedc6465ad63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-2aa35085995bdc1801daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-d0eb03bdfeea6084e0dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0100-5900000000-7d59ce683134a6f33e8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00or-9700000000-c13d2a2f6361459932dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-016r-8900000000-d7f12324cf02b0023aedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00or-9600000000-d51ee74ca89d43da53b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-1900000000-a44a9d75afd871a62687View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4r-4900000000-1b71b709786880019164View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-5900000000-56f78a7bdb3c091573a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a6r-9500000000-8140904c5eb795e92371View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9100000000-1175e50dbd23fc2a9922View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-f9e1437d75c6f5b25d88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-ad80f96e7d85d594f6cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-9300000000-57792ffddc2cccbd77b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0900000000-343bdc632cd1916d92c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-4900000000-c83c2058ae8923828aa6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00os-9100000000-840c225c8204e80727f2View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
unknown
General Function:
Nicotinate-nucleotide diphosphorylase (carboxylating) activity
Specific Function:
Involved in the catabolism of quinolinic acid (QA).
Gene Name:
nadC
Uniprot ID:
P30012
Molecular Weight:
32559.53 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
General Function:
Coenzyme transport and metabolism
Specific Function:
Nicotinate D-ribonucleotide + diphosphate + CO(2) = pyridine-2,3-dicarboxylate + 5-phospho-alpha-D-ribose 1- diphosphate
Gene Name:
nadC
Uniprot ID:
O06594
Molecular Weight:
29951.0 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23