Benzo[a]pyrene (CHEM000007)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (9)XML
Record Information
Version1.0
Creation Date2009-03-06 18:57:54 UTC
Update Date2016-11-09 01:08:08 UTC
Accession NumberCHEM000007
Identification
Common NameBenzo[a]pyrene
ClassSmall Molecule
DescriptionBenzo[a]pyrene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. It is one ingredient of cigarette. (5)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 1
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aromatic Hydrocarbon
  • Cigarette Toxin
  • Food Toxin
  • Industrial By-product/Pollutant
  • Industrial/Workplace Toxin
  • Natural Compound
  • Organic Compound
  • Pollutant
  • Polycyclic Aromatic Hydrocarbon
Chemical 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 Mass252.309 g/mol
Monoisotopic Mass252.094 g/mol
CAS Registry Number50-32-8
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
SMILESC1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C3
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearancePale yellow solid.
Experimental Properties
PropertyValue
Melting Point176.5°C
Boiling Point495 °C
Solubility1.62e-06 mg/mL at 25 °C [MAY,WE et al. (1983)]
Predicted Properties
PropertyValueSource
Water Solubility1.2e-06 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0590000000-6a1e4169eaee2450b6aaSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0390000000-d87401bcab72c45a1d87Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0090000000-aebdc23a6e4cb494681eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0590000000-6a1e4169eaee2450b6aaSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0390000000-d87401bcab72c45a1d87Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0090000000-aebdc23a6e4cb494681eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0090000000-4ed81317d745f20ae6d3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-f612ac63f25ab09a3fb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-da5273239d688cd66f49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-0090000000-fb6dcdd11a97e4d74479Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-31f8cde7b8fb38348ad0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-31f8cde7b8fb38348ad0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-f5fc2a06e6c04b87e62fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-969da6c938a324fffb4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-969da6c938a324fffb4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-969da6c938a324fffb4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-b5f9e841f69a96c6392aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-b5f9e841f69a96c6392aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0090000000-d38a61935d2a229c0c1fSpectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-0290000000-21f41e03667be1e6edcaSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
Mechanism of ToxicityThe ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. 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. The main carcinogenic metabolite of benzo(a)pyrene is the diol-epoxide trans-9,10-epoxy-7,8-dihydrodiol. (5, 6, 2, 3)
MetabolismPAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (5)
Toxicity ValuesLD50: 250 mg/kg (Intraperitoneal, Mouse) (8)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (7)
Uses/SourcesPAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and volcanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (5)
Minimum Risk LevelNot Available
Health EffectsPAHs 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. (5)
SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)
TreatmentThere is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (5)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0062469
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenzo(a)pyrene
Chemspider IDNot Available
ChEBI ID29865
PubChem Compound ID2336
Kegg Compound IDC07535
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11932001
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16256111
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16381670
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1844333
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26530167
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26703252
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=7561049
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=7721048