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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:29:27 UTC
Update Date2022-03-07 02:53:50 UTC
HMDB IDHMDB0033731
Secondary Accession Numbers
  • HMDB33731
Metabolite Identification
Common NameQuinoline
DescriptionQuinoline 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 found in alcoholic beverages. 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
Quinoline hydrochlorideMeSH
1-AzanaphthaleneHMDB
1-BenzazineHMDB
1-BenzineHMDB
2,3-BenzopyridineHMDB
benzo(b)PyridineHMDB
ChinoleineHMDB
ChinolineHMDB
FEMA 3470HMDB
LeucolHMDB
LeukolHMDB
QuinolinHMDB
Quinoline (8ci,9ci)HMDB
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

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-15.6 °CNot Available
Boiling Point239.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility6.11 mg/mL at 25 °CNot Available
LogP2.03Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.07831661259
DarkChem[M-H]-122.6431661259
DeepCCS[M+H]+126.43530932474
DeepCCS[M-H]-123.28330932474
DeepCCS[M-2H]-160.20730932474
DeepCCS[M+Na]+135.50330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
QuinolineC1=CC=C2N=CC=CC2=C11895.4Standard polar33892256
QuinolineC1=CC=C2N=CC=CC2=C11210.4Standard non polar33892256
QuinolineC1=CC=C2N=CC=CC2=C11244.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-4900000000-6650a64dcfaff97a384f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-0fb9-9700000000-162da149cecb7471177e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-0900000000-589a1fb16b83c4fe81152017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-5900000000-f63ba1bba58ccc63c20a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-4900000000-06d1e2a8216798421e172017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-4900000000-6650a64dcfaff97a384f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-0fb9-9700000000-162da149cecb7471177e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-0900000000-589a1fb16b83c4fe81152018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-5900000000-f63ba1bba58ccc63c20a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-4900000000-06d1e2a8216798421e172018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Quinoline EI-B (Non-derivatized)splash10-004i-2900000000-5f026eea98547624a47f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-0900000000-5bfb659404cb36aa304f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Quinoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-4900000000-f18da8f2e791614f0c9a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline LC-ESI-QQ , positive-QTOFsplash10-001i-0900000000-f80d7ca98d120817a55c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline LC-ESI-QQ , positive-QTOFsplash10-001i-0900000000-027cf5e71116c5fcb4b62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline LC-ESI-QQ , positive-QTOFsplash10-001i-0900000000-b503a364d204d8e6ac8c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline LC-ESI-QQ , positive-QTOFsplash10-004i-8900000000-49aa8f9641f21e97fc432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline LC-ESI-QQ , positive-QTOFsplash10-004i-9100000000-25969cc68eb743f7f3df2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-001i-0900000000-7ca73e074935b2add2f42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-001i-0900000000-a45f6683fe6d4b0b16aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-001i-0900000000-7026ebf0519b2fba00242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-001i-1900000000-09e171e9467e40b551d22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-0fai-4900000000-7b17c392210401ee485d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline ESI-ITFT , positive-QTOFsplash10-0fba-9700000000-581ee9456c67170a05202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline APCI-ITFT , positive-QTOFsplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline APCI-ITFT , positive-QTOFsplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline APCI-ITFT , positive-QTOFsplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Quinoline APCI-ITFT , positive-QTOFsplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinoline 10V, Positive-QTOFsplash10-001i-0900000000-6596d88125ed21410c6d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinoline 20V, Positive-QTOFsplash10-001i-0900000000-6c1f93bf41d02c99ce732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinoline 40V, Positive-QTOFsplash10-0ue9-3900000000-7293ce5372993b70ea552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinoline 10V, Negative-QTOFsplash10-004i-0900000000-f7d71396a8498e54005a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinoline 20V, Negative-QTOFsplash10-004i-0900000000-f7d71396a8498e54005a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Quinoline 40V, Negative-QTOFsplash10-004i-1900000000-678317c07cf462bbdfa92016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1583941
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.. .