Showing Compound Card for 7,8-Benzoquinoline (CDB005739)

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Record Information
Version1.0
Created at2020-04-27 16:50:54 UTC
Updated at2021-01-04 18:49:13 UTC
CannabisDB IDCDB005739
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name7,8-Benzoquinoline
Description7,8-Benzoquinoline or Benzo[h]quinoline also known as Benzoquinoline is a benzene derivative of quinoline in which the benzene group is fused to the C-7 and C-8 of quinoline. It 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. 7,8-Benzoquinoline exists as an off-white to brown crystalline powder. When heated to decomposition it emits toxic fumes. 7,8-Benzoquinoline causes skin and respiratory irritation and is known to cause serious eye irritation. Studies on rats have shown that 7,8-Benzoquinoline is able to induce both phase I (Cyp1A) and phase II (UDP-glucuronosyltransferase) activity towards certain drugs and therefore could function as a chemoprotective agent (PMID: 9176741 ). 7,8-Benzoquinoline is a constituent of marijuana (cannabis) smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
benzo(H)QuinolineMeSH
Chemical FormulaC13H9N
Average Molecular Weight179.22
Monoisotopic Molecular Weight179.0735
IUPAC Namebenzo[h]quinoline
Traditional Namebenzo(H)quinoline
CAS Registry Number230-27-3
SMILES
C1=CC=C2C(C=CC3=C2N=CC=C3)=C1
InChI Identifier
InChI=1S/C13H9N/c1-2-6-12-10(4-1)7-8-11-5-3-9-14-13(11)12/h1-9H
InChI KeyWZJYKHNJTSNBHV-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
  • Naphthalene
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.39ALOGPS
logP3.12ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)3.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.43 m³·mol⁻¹ChemAxon
Polarizability19.84 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-5fc66f3d3e9d275f61782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-afa1902a62cac9108abc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0900000000-f352ecec4acc52e48dc72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-56de673515f79a80ecbf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-56de673515f79a80ecbf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-96cf98f2c3f129dd64b72016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9191
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Le HT, Lamb JG, Franklin MR: Drug metabolizing enzyme induction by benzoquinolines, acridine, and quinacrine; tricyclic aromatic molecules containing a single heterocyclic nitrogen. J Biochem Toxicol. 1996;11(6):297-303. doi: 10.1002/(SICI)1522-7146(1996)11:6<297::AID-JBT5>3.0.CO;2-F. [PubMed:9176741 ]