Showing Compound Card for 1,2,3-Trimethylpyrene (CDB005899)

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Record Information
Version1.0
Created at2020-04-27 17:07:41 UTC
Updated at2021-01-06 19:06:58 UTC
CannabisDB IDCDB005899
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1,2,3-Trimethylpyrene
Description1,2,3-Trimethylpyrene 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.1,2,3-Trimethylpyrene 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 FormulaC19H16
Average Molecular Weight244.34
Monoisotopic Molecular Weight244.1252
IUPAC Name1,2,3-trimethylpyrene
Traditional Name1,2,3-trimethylpyrene
CAS Registry Number134145-12-3
SMILES
CC1=C(C)C2=CC=C3C=CC=C4C=CC(=C1C)C2=C34
InChI Identifier
InChI=1S/C19H16/c1-11-12(2)16-9-7-14-5-4-6-15-8-10-17(13(11)3)19(16)18(14)15/h4-10H,1-3H3
InChI KeyBYYRPCUKZCBJLB-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
logP6.08ALOGPS
logP5.82ChemAxon
logS-7.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.85 m³·mol⁻¹ChemAxon
Polarizability29.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
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 ID156046
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound179273
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 ]