CHEBI:29865 - benzo[a]pyrene

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ChEBI Name benzo[a]pyrene
ChEBI ID CHEBI:29865
ChEBI ASCII Name benzo[a]pyrene
Definition An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3045, CHEBI:22716
Supplier Information ChemicalBook:CB3696680, eMolecules:480189, ZINC000001530818
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Benzo[a]pyrene (BaP or B[a]P) is a polycyclic aromatic hydrocarbon and the result of incomplete combustion of organic matter at temperatures between 300 °C (572 °F) and 600 °C (1,112 °F). The ubiquitous compound can be found in coal tar, tobacco smoke and many foods, especially grilled meats. The substance with the formula C20H12 is one of the benzopyrenes, formed by a benzene ring fused to pyrene. Its diol epoxide metabolites, more commonly known as BPDE, react with 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 known to be connected to soot.
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Formula C20H12
Net Charge 0
Average Mass 252.30928
Monoisotopic Mass 252.09390
InChI 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
InChIKey FMMWHPNWAFZXNH-UHFFFAOYSA-N
SMILES c1ccc2c(c1)cc1ccc3cccc4ccc2c1c34
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
(via polycyclic arene )
Application(s): endocrine disruptor
Any compound that can disrupt the functions of the endocrine (hormone) system
(via polycyclic arene )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing benzo[a]pyrene (CHEBI:29865) has role carcinogenic agent (CHEBI:50903)
benzo[a]pyrene (CHEBI:29865) has role mouse metabolite (CHEBI:75771)
benzo[a]pyrene (CHEBI:29865) is a ortho- and peri-fused polycyclic arene (CHEBI:35300)
Incoming 7,8-dihydro-7-hydroxy-8S-glutathionylbenzo[a]pyrene (CHEBI:34479) has parent hydride benzo[a]pyrene (CHEBI:29865)
benzo[a]pyrene diol epoxide I (CHEBI:30614) has parent hydride benzo[a]pyrene (CHEBI:29865)
benzo[a]pyrene-7,8-dione (CHEBI:87752) has parent hydride benzo[a]pyrene (CHEBI:29865)
IUPAC Name
benzo[pqr]tetraphene
Synonyms Sources
(B(a)P) ChEBI
3,4-Benzopyrene NIST Chemistry WebBook
3,4-Benzpyrene NIST Chemistry WebBook
3,4-BP NIST Chemistry WebBook
Benzo(a)pyrene ChemIDplus
Benzo[a]pyrene KEGG COMPOUND
benzo[def]chrysene ChEBI
Benzpyrene KEGG COMPOUND
Benzpyrene KEGG COMPOUND
BP NIST Chemistry WebBook
Manual Xrefs Databases
Benzo(a)pyrene Wikipedia
C07535 KEGG COMPOUND
LSM-2198 LINCS
View more database links
Registry Numbers Types Sources
1911333 Reaxys Registry Number Reaxys
262573 Gmelin Registry Number Gmelin
50-32-8 CAS Registry Number KEGG COMPOUND
50-32-8 CAS Registry Number ChemIDplus
50-32-8 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11932001 PubMed citation Europe PMC
16256111 PubMed citation Europe PMC
16381670 PubMed citation Europe PMC
1844333 PubMed citation Europe PMC
26530167 PubMed citation Europe PMC
26703252 PubMed citation Europe PMC
7561049 PubMed citation Europe PMC
7721048 PubMed citation Europe PMC
Last Modified
24 February 2016