Record Information
Version1.0
Created at2020-04-27 17:10:35 UTC
Updated at2021-01-06 19:06:59 UTC
CannabisDB IDCDB005928
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBenzo[g h i]perylene
DescriptionBenzo[ghi]perylene, also known as 1,12-benzoperylene, belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system. Benzo[ghi]perylene is possibly neutral. Benzo[ghi]perylene is a polycyclic aromatic hydrocarbon with the chemical formula C22H12. Benzo[ghi]perylene is a potentially toxic compound. Benzoperylene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). They are usually found as a mixture containing two or more of these compounds. PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis (T3DB). Benzo[ghi]perylene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
Synonyms
ValueSource
1,12-BenzoperyleneKegg
1,12-BenzperyleneMeSH
Benzo(ghi)peryleneMeSH
Chemical FormulaC22H12
Average Molecular Weight276.33
Monoisotopic Molecular Weight276.0939
IUPAC Namehexacyclo[12.8.0.0^{2,11}.0^{3,8}.0^{4,21}.0^{17,22}]docosa-1(14),2,4,6,8,10,12,15,17(22),18,20-undecaene
Traditional Namehexacyclo[12.8.0.0^{2,11}.0^{3,8}.0^{4,21}.0^{17,22}]docosa-1(14),2,4,6,8,10,12,15,17(22),18,20-undecaene
CAS Registry Number191-24-2
SMILES
C1=CC2=CC=C3C=CC4=C5C6=C(C=CC=C6C(=C1)C2=C35)C=C4
InChI Identifier
InChI=1S/C22H12/c1-3-13-7-9-15-11-12-16-10-8-14-4-2-6-18-17(5-1)19(13)21(15)22(16)20(14)18/h1-12H
InChI KeyGYFAGKUZYNFMBN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPyrenes
Sub ClassBenzopyrenes
Direct ParentBenzopyrenes
Alternative Parents
Substituents
  • Benzo-e-pyrene
  • Triphenylene
  • Phenanthrene
  • Anthracene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
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
logP7.11ALOGPS
logP5.61ChemAxon
logS-8.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity90.94 m³·mol⁻¹ChemAxon
Polarizability31.44 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-0390000000-b385fdb32608e9f56e052014-09-20View Spectrum
Predicted GC-MSBenzo[g h i]perylene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-0090000000-664a1982d84ca4662f12Spectrum
Predicted GC-MSBenzo[g h i]perylene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-6d0d64f3ce64995022a52016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-6d0d64f3ce64995022a52016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0090000000-8bebc2915cc3cef4e2c22016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-8c80dd86f7df5879ab0d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-8c80dd86f7df5879ab0d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-53d7dab2090ab26b4e7e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-ebd61056e6d9044d4e5f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-ebd61056e6d9044d4e5f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0090000000-ebd61056e6d9044d4e5f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-bb1505f95acd68c6123d2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-bb1505f95acd68c6123d2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-bb1505f95acd68c6123d2021-10-12View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
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 ID8763
KEGG Compound IDC14318
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9117
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available