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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-23 01:51:42 UTC
Update Date2017-12-07 21:13:39 UTC
HMDB IDHMDB0062469
Secondary Accession Numbers
  • HMDB62469
Metabolite Identification
Common NameBenzo[a]pyrene
DescriptionBenzo[a]pyrene, also known as 3,4-Benzopyrene or 3,4-BP, is classified as a member of the Benzopyrenes. Benzopyrenes are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system. Benzo[a]pyrene is formally rated as a carcinogenic (IARC 1) potentially toxic compound. Benzo[a]pyrene is a crystalline, aromatic hydrocarbon consisting of five fused benzene rings and formed during the incomplete combustion of organic matter. Benzo[a]pyrene is primarily found in gasoline and diesel exhaust, cigarette smoke, coal tar and coal tar pitch, charcoal-broiled foods and certain other foods, amino acids, fatty acids and carbohydrate pyrolysis products, soot smoke, creosote oil, petroleum asphalt and shale oils. This substance is used only for research purposes. Benzo[a]pyrene is reasonably anticipated to be a human carcinogen (NCI05). Its diol epoxide metabolites (more commonly known as BPDE) react and bind to DNA, resulting in mutations and eventually cancer. It is listed as a Group 1 carcinogen by the IARC. In the 18th century a scrotal cancer of chimney sweepers, the chimney sweeps' carcinoma, was already connected to soot. [Wikipedia]
Structure
Thumb
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 BenzpyreneMeSH
3,4 BenzopyreneMeSH
Chemical FormulaC20H12
Average Molecular Weight252.3093
Monoisotopic Molecular Weight252.093900384
IUPAC Namepentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,8,10,12(20),13,15,17-decaene
Traditional Namebenzo(A)pyrene
CAS Registry Number50-32-8
SMILES
C1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C3
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
DescriptionThis compound 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0590000000-6a1e4169eaee2450b6aaView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0390000000-d87401bcab72c45a1d87View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0090000000-aebdc23a6e4cb494681eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0590000000-6a1e4169eaee2450b6aaView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-0390000000-d87401bcab72c45a1d87View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0090000000-aebdc23a6e4cb494681eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0090000000-4ed81317d745f20ae6d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-f612ac63f25ab09a3fb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-da5273239d688cd66f49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-0090000000-fb6dcdd11a97e4d74479View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-31f8cde7b8fb38348ad0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-31f8cde7b8fb38348ad0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-f5fc2a06e6c04b87e62fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-0290000000-21f41e03667be1e6edcaView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available