Quinaldic acid (CHEM034977)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:23:14 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034977
Identification
Common NameQuinaldic acid
ClassSmall Molecule
DescriptionA quinolinemonocarboxylic acid having the carboxy group at the 2-position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-CarboxyquinolineChEBI
2-ChinolincarbonsaeureChEBI
2-QuinolinecarboxylateChEBI
2-Quinolinecarboxylic acidChEBI
ChinaldinsaeureChEBI
QuinaldateChEBI
Quinaldinic acidChEBI
Quinoline-2-carboxylic acidChEBI
QuinaldinateGenerator
Quinoline-2-carboxylateGenerator
2-QuinolinylcarboxylateHMDB
2-Quinolinylcarboxylic acidHMDB
Quinolin-2-carboxylateHMDB
Quinolin-2-carboxylic acidHMDB
Quinaldic acidKEGG
Chemical FormulaC10H7NO2
Average Molecular Mass173.168 g/mol
Monoisotopic Mass173.048 g/mol
CAS Registry Number93-10-7
IUPAC Namequinoline-2-carboxylic acid
Traditional Namequinaldic acid
SMILESOC(=O)C1=NC2=C(C=CC=C2)C=C1
InChI IdentifierInChI=1S/C10H7NO2/c12-10(13)9-6-5-7-3-1-2-4-8(7)11-9/h1-6H,(H,12,13)
InChI KeyLOAUVZALPPNFOQ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-2-carboxylic acid
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.76 g/LALOGPS
logP1.44ALOGPS
logP0.79ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.1ChemAxon
pKa (Strongest Basic)5.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.86 m³·mol⁻¹ChemAxon
Polarizability17.27 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fc0-0940000000-3bb36ccb17eab5d4f216Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fc0-0940000000-3bb36ccb17eab5d4f216Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0umi-0900000000-201cc84404bb06e3a79cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9830000000-ff13ca054f835c494e4cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0089-1900000000-2ac6cea8f0ab44545a02Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-5900000000-0a29a5dcbe75bd2bfd65Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0089-1900000000-2ac6cea8f0ab44545a02Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006t-0900000000-e801df9cf80a4e3c1a8fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0fi9-1900000000-0953adea831044cdee87Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-3596e390d786fc0eb749Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udi-0900000000-a239b63d7915ec730a13Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-3900000000-3abada564f98738b98e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-002b-0900000000-bbdb7985eb8859a58918Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-006t-0900000000-d8dd2cceb2e32bda860aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-849a617e507a37a3486eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-5c60ff7dd4db050c5a55Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-f9801a644f0f5e8f799cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-5dfac4a5ac7a15be046aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0udi-5900000000-8c00a2a9c83a1524bd28Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-63da7eb04eb3050c0928Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0900000000-5b312e8793ea2ae6634aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0900000000-b7ccc79163ed5305afc0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-1900000000-75c1b662031ae1eb4e66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-3fb80b1e9de6c0075e62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fi0-0900000000-be8f80ef49f6303bd5aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-3e533cb46184c1bb4479Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-09b95cea4d0438cedeb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-ab7ccc734ae03b00fe88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-bd7d9eec2154eb38701fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02428
HMDB IDHMDB0000842
FooDB IDFDB022275
Phenol Explorer IDNot Available
KNApSAcK IDC00056094
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5805
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID6857
ChEBI ID18386
PubChem Compound ID7124
Kegg Compound IDC06325
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23801834
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=801703
3. Epand RM: The role of dietary ergothioneine in the development of diabetes mellitus. Med Hypotheses. 1982 Aug;9(2):207-13.
4. Okamoto H, Miyamoto S, Mabuchi H, Takeda R: Inhibition effect of quinaldic acid on glucose-induced insulin release from isolated Langerhans islets of the rat. Biochem Biophys Res Commun. 1974 Jul 24;59(2):623-9.
5. Ektova LV, Iartseva IV, Khorosheva EV, Ivanova TP, Iavorskaia NP, Mel'nik SIa: [Synthesis and biological properties of pyrimidine 2'-deoxynucleosides modified by a residue of quinaldic acid]. Bioorg Khim. 1995 Aug;21(8):625-31.
6. KAIHARA M, PRICE JM, TAKAHASHI H: The conversion of kynurenic acid to quinaldic acid by humans and rats. J Biol Chem. 1956 Dec;223(2):705-8.
7. Mittal A, Dabur R: Detection of new human metabolic urinary markers in chronic alcoholism and their reversal by aqueous extract of Tinospora cordifolia stem. Alcohol Alcohol. 2015 May;50(3):271-81. doi: 10.1093/alcalc/agv012. Epub 2015 Mar 8.
8. Noto Y, Okamoto H: Inhibition by kynurenine metabolites of proinsulin synthesis in isolated pancreatic islets. Acta Diabetol Lat. 1978 Sep-Dec;15(5-6):273-82. doi: 10.1007/BF02590750.
9. Langner E, Jeleniewicz W, Turski WA, Plech T: Quinaldic acid induces changes in the expression of p53 tumor suppressor both on protein and gene level in colon cancer LS180 cells. Pharmacol Rep. 2019 Apr;71(2):189-193. doi: 10.1016/j.pharep.2018.10.016. Epub 2018 Oct 30.