Showing Compound Card for 1-Methylpyrene (CDB005891)

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Record Information
Version1.0
Created at2020-04-27 17:06:53 UTC
Updated at2021-01-06 19:06:58 UTC
CannabisDB IDCDB005891
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1-Methylpyrene
Description1-Methylpyrene, belongs to the class of organic compounds known as pyrenes. Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. This colourless solid is the smallest peri-fused PAH (one where the rings are fused through more than one face). Pyrene results from the incomplete combustion of organic compounds, in a wide array of conditions. The aromaticity and peri-fused condition of pyrene make it a more stable combustion product than its isomer fluoranthene. 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. 1-Methylpyrene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC17H12
Average Molecular Weight216.28
Monoisotopic Molecular Weight216.0939
IUPAC Name1-methylpyrene
Traditional Name1-methylpyrene
CAS Registry Number27577-90-8
SMILES
CC1=C2C=CC3=CC=CC4=CC=C(C=C1)C2=C34
InChI Identifier
InChI=1S/C17H12/c1-11-5-6-14-8-7-12-3-2-4-13-9-10-15(11)17(14)16(12)13/h2-10H,1H3
InChI KeyKBSPJIWZDWBDGM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrenes. Pyrenes are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPyrenes
Sub ClassNot Available
Direct ParentPyrenes
Alternative Parents
Substituents
  • Pyrene
  • Phenanthrene
  • Naphthalene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP5.47ALOGPS
logP4.8ChemAxon
logS-7.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.76 m³·mol⁻¹ChemAxon
Polarizability25.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1-Methylpyrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-0090000000-1b89437f1380ed97961bSpectrum
Predicted GC-MS1-Methylpyrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-2f513d6daaa5aad7fd622016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-63ddd1e4385045ccd3a52016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-0490000000-fcc765c5d60f51d4f93c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-68beed3cad3b6b95bad92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-68beed3cad3b6b95bad92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0490000000-96d76c3a42af3e6d78a32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-3a79c9b7f17cf16e9ec02021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-3a79c9b7f17cf16e9ec02021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0290000000-bec0b8aeab1e60f90f592021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-7969b30be04233f0a8d52021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-7969b30be04233f0a8d52021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0190000000-46a5965c28a85455a1542021-10-12View 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 ID16043
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16932
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 ]