Showing Compound Card for Benzo [k] fluoranthene (CDB005913)

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Record Information
Version1.0
Created at2020-04-27 17:09:04 UTC
Updated at2021-01-06 19:06:59 UTC
CannabisDB IDCDB005913
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBenzo [k] fluoranthene
DescriptionBenzo[k]fluoranthene, also known as 11,12-benzofluoranthene, belongs to the class of organic compounds known as Fluoranthene is a polycyclic aromatic hydrocarbon (PAH) that consists of a naphthalene moiety connected by a five membered ring to a benzene. Fluoranthene is a colorless solid, although samples may appear as pale yellow. Fluoranthene is an isomer of pyrene and it results from the incomplete combustion of organic compounds, in a wide array of conditions. However, fluoranthene is less stable than pyrene and thus, less abundant. PAH metabolism occurs in all tissues, usually by cytochrome P-450, specifically by its associated enzymes CYP1A1 and CYP1B1 (PMID: 14720319 ). These enzymes metabolize PAH's into their toxic intermediates. The metabolites of pyrene, such as phenols, quinones, and dihydrodiols, can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. PAHs are generally considered as cancerogenic to varying degrees. Benzo[j]fluoranthene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11,12-BenzofluorantheneKegg
benzo(K)FluorantheneMeSH
Chemical FormulaC20H12
Average Molecular Weight252.31
Monoisotopic Molecular Weight252.0939
IUPAC Namepentacyclo[10.7.1.0^{2,11}.0^{4,9}.0^{16,20}]icosa-1(19),2,4,6,8,10,12,14,16(20),17-decaene
Traditional Namepentacyclo[10.7.1.0^{2,11}.0^{4,9}.0^{16,20}]icosa-1(19),2,4,6,8,10,12,14,16(20),17-decaene
CAS Registry Number207-08-9
SMILES
C1=CC=C2C=C3C4=CC=CC5=C4C(=CC=C5)C3=CC2=C1
InChI Identifier
InChI=1S/C20H12/c1-2-6-15-12-19-17-10-4-8-13-7-3-9-16(20(13)17)18(19)11-14(15)5-1/h1-12H
InChI KeyHAXBIWFMXWRORI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • 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
logP6.13ALOGPS
logP5.27ChemAxon
logS-7.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.17 m³·mol⁻¹ChemAxon
Polarizability29.59 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0udi-0390000000-7fadd00de7b666c8d6a42014-09-20View Spectrum
Predicted GC-MSBenzo [k] fluoranthene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-0090000000-0fb1e10e7f5d139722afSpectrum
Predicted GC-MSBenzo [k] fluoranthene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-f612ac63f25ab09a3fb72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-f612ac63f25ab09a3fb72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0090000000-da998b0ead23206d13982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-31f8cde7b8fb38348ad02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-31f8cde7b8fb38348ad02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-a7dc66f1d25898e308312016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-b5f9e841f69a96c6392a2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-b5f9e841f69a96c6392a2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0090000000-15c41a541f380aede3e02021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-969da6c938a324fffb4f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-969da6c938a324fffb4f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-969da6c938a324fffb4f2021-10-12View Spectrum
NMR
TypeDescriptionView
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 ID8804
KEGG Compound IDC14321
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Shimada T, Fujii-Kuriyama Y: Metabolic activation of polycyclic aromatic hydrocarbons to carcinogens by cytochromes P450 1A1 and 1B1. Cancer Sci. 2004 Jan;95(1):1-6. doi: 10.1111/j.1349-7006.2004.tb03162.x. [PubMed:14720319 ]