Kynurenic Acid

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Kynurenic Acid
Accession Number
DB11937
Type
Small Molecule
Groups
Investigational
Description

Kynurenic Acid is under investigation in clinical trial NCT02340325 (FS2 Safety and Tolerability Study in Healthy Volunteers).

Structure
Thumb
Synonyms
Not Available
Categories
UNII
H030S2S85J
CAS number
492-27-3
Weight
Average: 189.1675
Monoisotopic: 189.042593095
Chemical Formula
C10H7NO3
InChI Key
HCZHHEIFKROPDY-UHFFFAOYSA-N
InChI
InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)
IUPAC Name
4-oxo-1,4-dihydroquinoline-2-carboxylic acid
SMILES
OC(=O)C1=CC(=O)C2=CC=CC=C2N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAryl hydrocarbon receptorNot AvailableHuman
UG-protein coupled receptor 35Not AvailableHuman
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
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000715
KEGG Compound
C01717
PubChem Compound
3845
PubChem Substance
347828264
ChemSpider
3712
BindingDB
81975
ChEBI
18344
ChEMBL
CHEMBL299155
HET
KYA
PDB Entries
3av7 / 3wx9

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
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.954 mg/mLALOGPS
logP1.16ALOGPS
logP1.58ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity52.32 m3·mol-1ChemAxon
Polarizability18.05 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

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)GC-MSsplash10-0159-1985000000-f1c74ffc481c3d0faaa2
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0159-3895000000-6ba2750c5a9d9754abcc
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0159-0498000000-3db9df2c3d8456d7ba63
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-1985000000-f1c74ffc481c3d0faaa2
GC-MS Spectrum - GC-MSGC-MSsplash10-0159-3895000000-6ba2750c5a9d9754abcc
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-1895000000-e25b66b0b42d1928cc67
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-0900000000-7a5c54ced5b83f291e67
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0006-0900000000-e6b451ee354ed2717160
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-000i-9500000000-887e5157431b2908f31e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0006-1900000000-06f7059894cc245cb344
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0006-0900000000-89a88f44f08b8b68d5c1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-000f-0900000000-a4b194b85fef656b9b65
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-7862c532805b6036dc67
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-5fe3171fdaece30b78c8
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-df3b5b36289798800ad8
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-d4c11672b9479b2cd4b6
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-89a88f44f08b8b68d5c1
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-0900000000-9c26ffa9c04aa03d60f5
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0006-0900000000-6a8662ef19d900499a55
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0006-0900000000-d69a430b0eb34f38ad54
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-d0ef7c769d4985e85667
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ox-0900000000-2a593c8017254be4a387
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01ox-0900000000-59f3559c0b95c9411d2c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-02tc-0900000000-57dbbfb8e12c60951d77
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-1900000000-16ee11b3b9d30dd9e68c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-1900000000-06f7059894cc245cb344
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-c501751e61649c499767
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-51e6b7c920848310eccc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0900000000-49a60bc6d08b6675b6c2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014l-0900000000-3a256522dd8694fe04c0
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinoline carboxylic acids
Direct Parent
Quinoline carboxylic acids
Alternative Parents
Hydroquinolones / Hydroquinolines / Pyridinecarboxylic acids / Benzenoids / Vinylogous amides / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Quinoline-2-carboxylic acid / Dihydroquinolone / Dihydroquinoline / Pyridine carboxylic acid / Pyridine carboxylic acid or derivatives / Pyridine / Benzenoid / Heteroaromatic compound / Vinylogous amide / Monocarboxylic acid or derivatives
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monohydroxyquinoline, quinolinemonocarboxylic acid (CHEBI:18344)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. DiNatale BC, Murray IA, Schroeder JC, Flaveny CA, Lahoti TS, Laurenzana EM, Omiecinski CJ, Perdew GH: Kynurenic acid is a potent endogenous aryl hydrocarbon receptor ligand that synergistically induces interleukin-6 in the presence of inflammatory signaling. Toxicol Sci. 2010 May;115(1):89-97. doi: 10.1093/toxsci/kfq024. Epub 2010 Jan 27. [PubMed:20106948]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
G-protein coupled receptor activity
Specific Function
Acts as a receptor for kynurenic acid, an intermediate in the tryptophan metabolic pathway. The activity of this receptor is mediated by G-proteins that elicit calcium mobilization and inositol pho...
Gene Name
GPR35
Uniprot ID
Q9HC97
Uniprot Name
G-protein coupled receptor 35
Molecular Weight
34071.89 Da
References
  1. Zhao P, Sharir H, Kapur A, Cowan A, Geller EB, Adler MW, Seltzman HH, Reggio PH, Heynen-Genel S, Sauer M, Chung TD, Bai Y, Chen W, Caron MG, Barak LS, Abood ME: Targeting of the orphan receptor GPR35 by pamoic acid: a potent activator of extracellular signal-regulated kinase and beta-arrestin2 with antinociceptive activity. Mol Pharmacol. 2010 Oct;78(4):560-8. doi: 10.1124/mol.110.066746. Epub 2010 Jul 22. [PubMed:20826425]

Drug created on October 20, 2016 15:02 / Updated on November 02, 2018 07:17