Showing Compound Card for 1-Methylphenanthrene (CDB005872)

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Record Information
Version1.0
Created at2020-04-27 17:04:59 UTC
Updated at2021-01-06 19:06:58 UTC
CannabisDB IDCDB005872
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1-Methylphenanthrene
Description1-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. 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 FormulaC15H12
Average Molecular Weight192.26
Monoisotopic Molecular Weight192.0939
IUPAC Name1-methylphenanthrene
Traditional Name1-methylphenanthrene
CAS Registry Number832-69-9
SMILES
CC1=C2C=CC3=CC=CC=C3C2=CC=C1
InChI Identifier
InChI=1S/C15H12/c1-11-5-4-8-15-13(11)10-9-12-6-2-3-7-14(12)15/h2-10H,1H3
InChI KeyDOWJXOHBNXRUOD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • 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
logP5.05ALOGPS
logP4.47ChemAxon
logS-6.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity64 m³·mol⁻¹ChemAxon
Polarizability22.57 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, Positivesplash10-0006-0900000000-ee0d8c682df338cdb9b92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-043b30e76ced3b1943312016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-1900000000-af6e33c687c49d563a0a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-6c296ba360d26f3c1d492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-6c296ba360d26f3c1d492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-26f13ca7f25084a132b52016-08-03View 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 IDC19457
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13257
PDB IDNot Available
ChEBI ID35860
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 ]