Quinolinic Acid

Identification

Name
Quinolinic Acid
Accession Number
DB01796  (EXPT02391)
Type
Small Molecule
Groups
Experimental
Description

A 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
Synonyms
Not Available
Categories
UNII
F6F0HK1URN
CAS number
89-00-9
Weight
Average: 167.1189
Monoisotopic: 167.021857653
Chemical Formula
C7H5NO4
InChI Key
GJAWHXHKYYXBSV-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

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNicotinate-nucleotide pyrophosphorylase [carboxylating]Not AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UNicotinate-nucleotide pyrophosphorylase [carboxylating]Not AvailableMycobacterium tuberculosis
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
Nicotinate and Nicotinamide MetabolismMetabolic
NAD BiosynthesisMetabolic
NAD MetabolismMetabolic
Nicotinate and Nicotinamide MetabolismMetabolic
Tryptophan MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0000232
KEGG Compound
C03722
PubChem Compound
1066
PubChem Substance
46505240
ChemSpider
1037
BindingDB
26115
ChEBI
16675
ChEMBL
CHEMBL286204
HET
NTM
PDB Entries
1qap / 1qpq / 2b7n / 3c2o / 4ywd / 4zk6 / 5ayy / 5kto / 5lqs / 6f4l

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)228.5 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0002-0910000000-a8eacf1916c539d286b6
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0910000000-64e9e4b901dd69dc90c5
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-006t-7910000000-0bb1a7ce8a5907feae21
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-05i0-9500000000-555e92ebc410fc53e92f
GC-MS Spectrum - EI-BGC-MSsplash10-0100-5900000000-3d726d602fec21fd8beb
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0910000000-a8eacf1916c539d286b6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0910000000-64e9e4b901dd69dc90c5
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-006t-7910000000-0bb1a7ce8a5907feae21
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-1960000000-8197ee161fa149deabdd
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0920000000-40d676712c981904799f
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0002-0900000000-4a6d37bd8578b50cf677
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-004i-9100000000-45dc448cbedc6465ad63
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-004i-9000000000-2aa35085995bdc1801da
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-014i-0900000000-d0eb03bdfeea6084e0db
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0100-5900000000-7d59ce683134a6f33e8d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00or-9700000000-c13d2a2f6361459932db
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-016r-8900000000-d7f12324cf02b0023aed
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-00or-9600000000-d51ee74ca89d43da53b4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0udi-1900000000-a44a9d75afd871a62687
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0a4r-4900000000-1b71b709786880019164
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0a4i-5900000000-56f78a7bdb3c091573a7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0a6r-9500000000-8140904c5eb795e92371
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-004i-9100000000-1175e50dbd23fc2a9922
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-f9e1437d75c6f5b25d88
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-ad80f96e7d85d594f6cb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-9300000000-57792ffddc2cccbd77b9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-0900000000-343bdc632cd1916d92c9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fr-4900000000-c83c2058ae8923828aa6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00os-9100000000-840c225c8204e80727f2
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0900000000-9a963e41421edb041561
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0900000000-4c0c9b98c2ce00d0d282
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-d0eb03bdfeea6084e0db
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0100-5900000000-4af865513d09a8bab44f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00or-9700000000-c13d2a2f6361459932db
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-016r-8900000000-ff25a1c9823ecb018549
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00or-9600000000-d51ee74ca89d43da53b4
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0900000000-9aae7c1fea6c004e9a69
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0900000000-738f4d5b9ac02d750938
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0900000000-15b9defdbe16fc3862e0
MS/MS Spectrum - , negativeLC-MS/MSsplash10-00di-0900000000-0f75a31fb21a47946ce3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-be59efebd27c9ead86f3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fk9-0900000000-451e2c803b494b6470d1
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-2900000000-44254e622ab95d3e8de7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-88300d62153cc9ab0a7a
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-8d708be6f669c4c7d590
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-3caad5bf54891863742a
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004j-0900000000-f85d858923b491e70a60
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-002b-0900000000-34db1ea2882c0a8c99c9
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyridinecarboxylic acids and derivatives
Direct Parent
Pyridinecarboxylic acids
Alternative Parents
Dicarboxylic acids and derivatives / Heteroaromatic compounds / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
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
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridinedicarboxylic acid (CHEBI:16675)

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
Uniprot Name
Nicotinate-nucleotide pyrophosphorylase [carboxylating]
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
Involved in the catabolism of quinolinic acid (QA).
Specific Function
Nicotinate-nucleotide diphosphorylase (carboxylating) activity
Gene Name
nadC
Uniprot ID
P9WJJ7
Uniprot Name
Nicotinate-nucleotide pyrophosphorylase [carboxylating]
Molecular Weight
29950.79 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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:06