Showing Compound Card for Benzo [a] pyrene (CDB005916)

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Record Information
Version1.0
Created at2020-04-27 17:09:22 UTC
Updated at2021-01-06 19:06:59 UTC
CannabisDB IDCDB005916
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBenzo [a] pyrene
DescriptionBenzo[a]pyrene, also known as 3,4-benzopyrene or 3,4-BP, belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system. Benzo[a]pyrene is possibly neutral. Benzo[a]pyrene is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Benzopyrene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning of organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. These enzymes metabolize PAH's into their toxic intermediates. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body (T3DB). Benzo[a]pyrene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(b(a)p)ChEBI
3,4-BenzopyreneChEBI
3,4-BenzpyreneChEBI
3,4-BPChEBI
Benzo(a)pyreneChEBI
Benzo[def]chryseneChEBI
BenzpyreneChEBI
BPChEBI
3,4 BenzpyreneHMDB
3,4 BenzopyreneHMDB
Chemical FormulaC20H12
Average Molecular Weight252.31
Monoisotopic Molecular Weight252.0939
IUPAC Namepentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene
Traditional Namepentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene
CAS Registry Number50-32-8
SMILES
C1=CC=C2C(=C1)C=C1C=CC3=CC=CC4=CC=C2C1=C34
InChI Identifier
InChI=1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H
InChI KeyFMMWHPNWAFZXNH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPyrenes
Sub ClassBenzopyrenes
Direct ParentBenzopyrenes
Alternative Parents
Substituents
  • Benzo-a-pyrene
  • Chrysene
  • Phenanthrene
  • Anthracene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Role

Environmental role:

Indirect biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.2e-06 g/lALOGPS
logP6.39ALOGPS
Predicted Properties
PropertyValueSource
logP6.39ALOGPS
logP5.27ChemAxon
logS-8.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.17 m³·mol⁻¹ChemAxon
Polarizability29.09 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0udi-0290000000-21f41e03667be1e6edca2014-09-20View Spectrum
GC-MSBenzo [a] pyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0590000000-6a1e4169eaee2450b6aaSpectrum
GC-MSBenzo [a] pyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0390000000-d87401bcab72c45a1d87Spectrum
GC-MSBenzo [a] pyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0090000000-aebdc23a6e4cb494681eSpectrum
GC-MSBenzo [a] pyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0590000000-6a1e4169eaee2450b6aaSpectrum
GC-MSBenzo [a] pyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0390000000-d87401bcab72c45a1d87Spectrum
GC-MSBenzo [a] pyrene, non-derivatized, GC-MS Spectrumsplash10-0udi-0090000000-aebdc23a6e4cb494681eSpectrum
Predicted GC-MSBenzo [a] pyrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-0090000000-4ed81317d745f20ae6d3Spectrum
Predicted GC-MSBenzo [a] pyrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-f612ac63f25ab09a3fb72016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-da5273239d688cd66f492016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-0090000000-fb6dcdd11a97e4d744792016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-31f8cde7b8fb38348ad02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-31f8cde7b8fb38348ad02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-f5fc2a06e6c04b87e62f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-969da6c938a324fffb4f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-969da6c938a324fffb4f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-969da6c938a324fffb4f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-b5f9e841f69a96c6392a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-b5f9e841f69a96c6392a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0090000000-d38a61935d2a229c0c1f2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 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 IDHMDB0062469
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07535
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzo(a)pyrene
METLIN IDNot Available
PubChem Compound2336
PDB IDNot Available
ChEBI ID29865
References
General ReferencesNot Available