Showing Compound Card for Quinoline (CDB005360)

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Record Information
Version1.0
Created at2020-04-27 16:12:52 UTC
Updated at2021-01-04 20:37:40 UTC
CannabisDB IDCDB005360
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameQuinoline
DescriptionQuinoline, C9H7N, also known as benzo[b]pyridine or chinolin, is a heterocyclic, aromatic compounds that 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. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. Quinoline is a strongly basic compound that is a colourless hygroscopic oily liquid with a strong medicinal, musty, tobacco, leathery odour ( Ref:DOI ). Quinoline is slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Aged samples of quinoline, if exposed to light, become yellow and later brown. Quinoline is an alkaloid from various plant species including Mentha species. It is also present in cocoa, coffee, black tea, tobacco burley, fig leaf, tea plant, cooked rice,  dried bonito and in alcoholic beverages such as scotch whiskey ( Ref:DOI ). Approximately 4 tonnes of quinoline are produced annually according to a report published in 2005. Quinoline is mainly used as a building block to other chemicals, such as 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 creates quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name "Assert". Quinoline is also found in cannabis smoke. It is formed during the combustion of cannabis ( Ref:DOI ). 
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight129.16
Monoisotopic Molecular Weight129.0578
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 Point237 °C at 760 mm HgWikipedia
Water Solubility6.11 mg/mL at 25 °CNot Available
logP2.03Not Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-4900000000-f18da8f2e791614f0c9a2014-09-20View Spectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-6650a64dcfaff97a384fSpectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-0fb9-9700000000-162da149cecb7471177eSpectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-589a1fb16b83c4fe8115Spectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-5900000000-f63ba1bba58ccc63c20aSpectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-06d1e2a8216798421e17Spectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5f026eea98547624a47fSpectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5f026eea98547624a47fSpectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-6650a64dcfaff97a384fSpectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-0fb9-9700000000-162da149cecb7471177eSpectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-589a1fb16b83c4fe8115Spectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-5900000000-f63ba1bba58ccc63c20aSpectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-06d1e2a8216798421e17Spectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5f026eea98547624a47fSpectrum
GC-MSQuinoline , non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5f026eea98547624a47fSpectrum
Predicted GC-MSQuinoline , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fb9-0900000000-5bfb659404cb36aa304fSpectrum
Predicted GC-MSQuinoline , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuinoline , non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-f80d7ca98d120817a55c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-027cf5e71116c5fcb4b62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-b503a364d204d8e6ac8c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-8900000000-49aa8f9641f21e97fc432017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-25969cc68eb743f7f3df2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7ca73e074935b2add2f42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-a45f6683fe6d4b0b16aa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7026ebf0519b2fba00242017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-1900000000-09e171e9467e40b551d22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fai-4900000000-7b17c392210401ee485d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fba-9700000000-581ee9456c67170a05202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-6596d88125ed21410c6d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-6c1f93bf41d02c99ce732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-3900000000-7293ce5372993b70ea552016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-f7d71396a8498e54005a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-f7d71396a8498e54005a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-678317c07cf462bbdfa92016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0033731
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available