Showing Compound Card for Pyrene (CDB005878)

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Record Information
Version1.0
Created at2020-04-27 17:05:34 UTC
Updated at2021-01-06 19:06:58 UTC
CannabisDB IDCDB005878
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePyrene
DescriptionFluoranthene, also known as benzo[JK]fluorene, belongs to the class of organic compounds known as polycyclic aromatic hydrocarbons (PAH) and it consists of a naphthalene moiety connected by a five membered ring to a benzene ring. Fluoranthene is a colorless solid, although samples may appear as pale yellow. It is an isomer of pyrene and it also results from the incomplete combustion of organic compounds, in a wide array of conditions. However, fluoranthene is the 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. They may also cause reproductive effects and depress the immune system. Fluoranthene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Benzo[def]phenanthreneChEBI
beta-PyreneChEBI
PyrenChEBI
b-PyreneGenerator
Β-pyreneGenerator
BenzpyreneHMDB
Coal tar pitch volatiles:pyreneHMDB
Pyrene (acd/name 4.0)HMDB
{Benzo[def]phenanthrene}HMDB
Chemical FormulaC16H10
Average Molecular Weight202.25
Monoisotopic Molecular Weight202.0783
IUPAC Namepyrene
Traditional Namepyrene
CAS Registry Number129-00-0
SMILES
C1=CC2=CC=C3C=CC=C4C=CC(=C1)C2=C34
InChI Identifier
InChI=1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H
InChI KeyBBEAQIROQSPTKN-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 Descriptors
Ontology
Disposition

Source:

Route of exposure:

Biological location:

Role

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point151.2 °CNot Available
Boiling Point404 °CWikipedia
Water Solubility0.00014 mg/mL at 25 °CNot Available
logP4.88Not Available
Predicted Properties
PropertyValueSource
logP5.19ALOGPS
logP4.28ChemAxon
logS-6.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity66.72 m³·mol⁻¹ChemAxon
Polarizability22.86 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0udi-0190000000-3f6dbb289af8f6c988fb2014-09-20View Spectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-3490000000-a0f4fc47f1f625d9dda5Spectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0390000000-aed9be9c54a99a10a772Spectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0190000000-ab79745741c952b34e15Spectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-1290000000-1f9a049804cf2fb46ba3Spectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0090000000-838134ca9d5c1b6a304aSpectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-3490000000-a0f4fc47f1f625d9dda5Spectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0390000000-aed9be9c54a99a10a772Spectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0190000000-ab79745741c952b34e15Spectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-1290000000-1f9a049804cf2fb46ba3Spectrum
GC-MSPyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0090000000-838134ca9d5c1b6a304aSpectrum
Predicted GC-MSPyrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-0090000000-023bdea6eb26657bf7c2Spectrum
Predicted GC-MSPyrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-8a4ffb969c6480f4a0f92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-8a4ffb969c6480f4a0f92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0190000000-cf9d9c3c3318712878832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-e5a45f3b87aa2e8b24042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-e5a45f3b87aa2e8b24042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-650c1cb3eed690571b3a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6aba671a40209155866b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-6aba671a40209155866b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-6aba671a40209155866b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-d631c56cd3c088dbebc42021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-d631c56cd3c088dbebc42021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0090000000-37848fb7edb6a1e2deda2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0042002
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00014864
Chemspider ID29153
KEGG Compound IDC14335
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrene
METLIN IDNot Available
PubChem Compound31423
PDB IDNot Available
ChEBI ID39106
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 ]