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 No supplier information found for this compound.
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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
Last Modified
24 February 2016