Identification
- Generic Name
- Quinolinic Acid
- DrugBank Accession Number
- DB01796
- Background
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]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Quinolinic Acid (DB01796)
- Weight
- Average: 167.1189
Monoisotopic: 167.021857653 - Chemical Formula
- C7H5NO4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UNicotinate-nucleotide pyrophosphorylase [carboxylating] Not Available Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720) UNicotinate-nucleotide pyrophosphorylase [carboxylating] Not Available Mycobacterium 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Nicotinate and Nicotinamide Metabolism Metabolic Tryptophan Metabolism Metabolic - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aromatic heteromonocyclic compound / Azacycle / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyridinedicarboxylic acid (CHEBI:16675)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- F6F0HK1URN
- CAS number
- 89-00-9
- 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
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
- ZINC
- ZINC000000331671
- PDBe Ligand
- NTM
- PDB Entries
- 1qap / 1qpq / 2b7n / 3c2o / 4ywd / 4zk6 / 5ayy / 5kto / 5lqs / 6f4l … show 1 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 228.5 °C PhysProp water solubility 1.1E+004 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) pKa 2.43 PERRIN,DD (1972) - Predicted Properties
Property Value Source Water Solubility 4.07 mg/mL ALOGPS logP 0.15 ALOGPS logP -1.2 Chemaxon logS -1.6 ALOGPS pKa (Strongest Acidic) 0.31 Chemaxon pKa (Strongest Basic) 6.67 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 87.49 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 38.04 m3·mol-1 Chemaxon Polarizability 14.34 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.823 Blood Brain Barrier + 0.7119 Caco-2 permeable + 0.5533 P-glycoprotein substrate Non-substrate 0.7874 P-glycoprotein inhibitor I Non-inhibitor 0.9823 P-glycoprotein inhibitor II Non-inhibitor 0.9947 Renal organic cation transporter Non-inhibitor 0.9413 CYP450 2C9 substrate Non-substrate 0.8066 CYP450 2D6 substrate Non-substrate 0.8884 CYP450 3A4 substrate Non-substrate 0.8135 CYP450 1A2 substrate Non-inhibitor 0.9757 CYP450 2C9 inhibitor Non-inhibitor 0.9556 CYP450 2D6 inhibitor Non-inhibitor 0.9578 CYP450 2C19 inhibitor Non-inhibitor 0.9672 CYP450 3A4 inhibitor Non-inhibitor 0.9822 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9921 Ames test Non AMES toxic 0.9796 Carcinogenicity Non-carcinogens 0.9191 Biodegradation Ready biodegradable 0.7561 Rat acute toxicity 2.4057 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9853 hERG inhibition (predictor II) Non-inhibitor 0.9815
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 134.4812613 predictedDarkChem Lite v0.1.0 [M-H]- 130.0285391 predictedDarkChem Standard v0.1.0 [M-H]- 134.5220613 predictedDarkChem Lite v0.1.0 [M-H]- 134.3119613 predictedDarkChem Lite v0.1.0 [M-H]- 128.23999 predictedDeepCCS 1.0 (2019) [M+H]+ 134.5854613 predictedDarkChem Lite v0.1.0 [M+H]+ 134.6202693 predictedDarkChem Standard v0.1.0 [M+H]+ 134.7431613 predictedDarkChem Lite v0.1.0 [M+H]+ 134.9176613 predictedDarkChem Lite v0.1.0 [M+H]+ 132.06734 predictedDeepCCS 1.0 (2019) [M+Na]+ 134.4168613 predictedDarkChem Lite v0.1.0 [M+Na]+ 134.3704613 predictedDarkChem Lite v0.1.0 [M+Na]+ 134.5198613 predictedDarkChem Lite v0.1.0 [M+Na]+ 134.3440613 predictedDarkChem Lite v0.1.0 [M+Na]+ 141.02916 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52