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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:29:27 UTC
Update Date2019-07-23 06:14:11 UTC
HMDB IDHMDB0033731
Secondary Accession Numbers
  • HMDB33731
Metabolite Identification
Common NameQuinoline
DescriptionQuinoline is found in alcoholic beverages. Quinoline is an alkaloid from various plant species including Mentha species. Also present in cocoa, black tea and scotch whiskey. Quinoline is a flavouring ingredient Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. Aged samples, if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline is mainly used as a building block to other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.[citation needed] Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its 2- and 4-methyl derivatives are precursors to cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert"
Structure
Data?1563862451
Synonyms
ValueSource
Benzo[b]pyridineChEBI
ChinolinChEBI
1-AzanaphthaleneHMDB
1-BenzazineHMDB
1-BenzineHMDB
2,3-BenzopyridineHMDB
Benzo(b)pyridineHMDB
ChinoleineHMDB
ChinolineHMDB
FEMA 3470HMDB
LeucolHMDB
LeukolHMDB
QuinolinHMDB
Quinoline (8ci,9ci)HMDB
Quinoline hydrochlorideHMDB
Chemical FormulaC9H7N
Average Molecular Weight129.1586
Monoisotopic Molecular Weight129.057849229
IUPAC Namequinoline
Traditional Namecinch
CAS Registry Number91-22-5
SMILES
C1=CC=C2N=CC=CC2=C1
InChI Identifier
InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
InChI KeySMWDFEZZVXVKRB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassNot Available
Direct ParentQuinolines and derivatives
Alternative Parents
Substituents
  • Quinoline
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-15.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.11 mg/mL at 25 °CNot Available
LogP2.03Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.37 g/LALOGPS
logP2.19ALOGPS
logP2.13ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.98 m³·mol⁻¹ChemAxon
Polarizability13.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-6650a64dcfaff97a384fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9700000000-162da149cecb7471177eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-589a1fb16b83c4fe8115Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-f63ba1bba58ccc63c20aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-06d1e2a8216798421e17Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-6650a64dcfaff97a384fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-9700000000-162da149cecb7471177eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-0900000000-589a1fb16b83c4fe8115Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-5900000000-f63ba1bba58ccc63c20aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-4900000000-06d1e2a8216798421e17Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-0900000000-5bfb659404cb36aa304fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-f80d7ca98d120817a55cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-027cf5e71116c5fcb4b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-b503a364d204d8e6ac8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-8900000000-49aa8f9641f21e97fc43Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-25969cc68eb743f7f3dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7ca73e074935b2add2f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-a45f6683fe6d4b0b16aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7026ebf0519b2fba0024Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-1900000000-09e171e9467e40b551d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fai-4900000000-7b17c392210401ee485dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fba-9700000000-581ee9456c67170a0520Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-6596d88125ed21410c6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-6c1f93bf41d02c99ce73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-3900000000-7293ce5372993b70ea55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-f7d71396a8498e54005aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-f7d71396a8498e54005aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-678317c07cf462bbdfa9Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-4900000000-f18da8f2e791614f0c9aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011854
KNApSAcK IDC00026478
Chemspider ID6780
KEGG Compound IDC06413
BioCyc IDQUINOLINE
BiGG IDNot Available
Wikipedia LinkQuinoline
METLIN IDNot Available
PubChem Compound7047
PDB IDNot Available
ChEBI ID17362
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ruger A, Schwarz G, Lingens F: Microbial metabolism of quinoline and related compounds. XIX. Degradation of 4-methylquinoline and quinoline by Pseudomonas putida K1. Biol Chem Hoppe Seyler. 1993 Jul;374(7):479-88. [PubMed:8216899 ]
  2. Van Caekenberghe DL, Pattyn SR: In vitro activity of ciprofloxacin compared with those of other new fluorinated piperazinyl-substituted quinoline derivatives. Antimicrob Agents Chemother. 1984 Apr;25(4):518-21. [PubMed:6732221 ]
  3. Xu XD, Hu XR, Yang JS: [Review of studies on active components of antitumor medicinal plants]. Zhongguo Zhong Yao Za Zhi. 2008 Sep;33(17):2073-81. [PubMed:19066044 ]
  4. Musiol R, Serda M, Hensel-Bielowka S, Polanski J: Quinoline-based antifungals. Curr Med Chem. 2010;17(18):1960-73. [PubMed:20377510 ]
  5. Solomon VR, Lee H: Quinoline as a privileged scaffold in cancer drug discovery. Curr Med Chem. 2011;18(10):1488-508. [PubMed:21428893 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .