Showing Compound Card for Methylfluoranthene (CDB005882)

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Record Information
Version1.0
Created at2020-04-27 17:05:58 UTC
Updated at2021-01-06 19:06:58 UTC
CannabisDB IDCDB005882
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethylfluoranthene
Description7-Ethyl-1-methylphenanthrene belongs to the class of organic compounds known as phenanthrenes and derivatives. Phenanthrenes are polycyclic aromatic hydrocarbon (PAH) compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene rings. The name 'phenanthrene' is a composite of phenyl and anthracene. In its pure form it appears as a colorless, crystal-like solid but can also look yellow. Phenanthrene is used to make dyes, plastics and pesticides, explosives and drugs. It has also been used to make bile acids, cholesterol and steroids. Phenanthrene is nearly insoluble in water but is soluble in most low polarity organic solvents such as toluene, carbon tetrachloride, ether, chloroform, acetic acid and benzene. Phenanthrene is a potentially toxic compound. It can be found in cigarette smoke and is a known irritant and it photosensitizes skin to light. 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 PAHs, 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. 7-Ethyl-1-methylphenanthrene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC17H12
Average Molecular Weight216.28
Monoisotopic Molecular Weight216.0939
IUPAC Name1-methylfluoranthene
Traditional Name1-methylfluoranthene
CAS Registry Number25889-60-5
SMILES
CC1=C2C3=CC=CC=C3C3=CC=CC(C=C1)=C23
InChI Identifier
InChI=1S/C17H12/c1-11-9-10-12-5-4-8-15-13-6-2-3-7-14(13)16(11)17(12)15/h2-10H,1H3
InChI KeyXTJQJDCUHJRGCX-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
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
logP5.44ALOGPS
logP4.8ChemAxon
logS-6.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.76 m³·mol⁻¹ChemAxon
Polarizability25.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 ID129629
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound146998
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 ]