Benzo(a)pyrene metabolism (Homo sapiens)

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1-7IsomerisationAutoxidationDNA adductsDNA adducts+ Reactive oxygen speciesAKR1C2AKR1C1Benzo[a]pyrene-9-sulfate7,8-dihydroxy-7,8-dihydro-benzo[a]pyreneBenzo[a]pyrene-7-glucuronideAKR1C4Benzo[a]pyrene-7-sulfateBenzo[a]pyrene-7,8-dione6-hydroxy-benzo[a]pyrene9,10-epoxy-7,8-dihydroxy-7,8-dihydro-benzo[a]pyreneBenzo[a]pyreneAKR1A1AKR1C3CYP1A1GlucuronosyltransferaseEPHX1Benzo[a]pyrene-1,6-dione3-hydroxy-benzo[a]pyrene7,8-epoxy-benzo[a]pyrene9-hydroxy-benzo[a]pyreneSULTBenzo[a]pyrene-3,6-dioneCytochrome P450 peroxidaseCYP1B1CYP1B17-hydroxy-benzo[a]pyreneBenzo[a]pyrene radical cationBenzo[a]pyrene-9-glucuronideCYP1A1Benzo[a]pyrene-6,12-dioneCYP3A4


Description

Benzene metabolism primarily takes place in the liver, to a variety of products that are transported to the bone marrow where additional metabolism occurs. Several metabolites of benzene are responsible for the toxic effects of benzene including reactive metabolites that covalently bind macromolecules and induce oxidative damage.

Quality Tags

Ontology Terms

 

Bibliography

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  1. Jin Y, Penning TM; ''Aldo-keto reductases and bioactivation/detoxication.''; Annu Rev Pharmacol Toxicol, 2007 PubMed
  2. Kisselev P, Schwarz D, Platt KL, Schunck WH, Roots I; ''Epoxidation of benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1 in reconstituted membranes. Effects of charge and nonbilayer phase propensity of the membrane.''; Eur J Biochem, 2002 PubMed
  3. Malejka-Giganti D, Ritter CL; ''Peroxidative metabolism of carcinogenic N-arylhydroxamic acids: implications for tumorigenesis.''; Environ Health Perspect, 1994 PubMed
  4. Jiang H, Gelhaus SL, Mangal D, Harvey RG, Blair IA, Penning TM; ''Metabolism of benzo[a]pyrene in human bronchoalveolar H358 cells using liquid chromatography-mass spectrometry.''; Chem Res Toxicol, 2007 PubMed
  5. Boysen G, Hecht SS; ''Analysis of DNA and protein adducts of benzo[a]pyrene in human tissues using structure-specific methods.''; Mutat Res, 2003 PubMed
  6. Luch A; ''Nature and nurture - lessons from chemical carcinogenesis.''; Nat Rev Cancer, 2005 PubMed
  7. Snyder R, Hedli CC; ''An overview of benzene metabolism.''; Environ Health Perspect, 1996 PubMed

History

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CompareRevisionActionTimeUserComment
94805view23:59, 5 October 2017AlexanderPicoConverted lines, added catalysis types, connected interactions
94804view23:56, 5 October 2017AlexanderPicoModified description
89537view11:07, 16 September 2016Mkutmonontology tag fix
89474view13:39, 15 September 2016Mkutmonremove space from ontology term id
85085view22:47, 12 April 2016EgonwAdded a few metabolite identifiers.
72081view20:46, 24 October 2013EgonwAdded a few identifiers.
69008view17:46, 8 July 2013MaintBotUpdated to 2013 gpml schema
67077view10:03, 26 June 2013Christine ChichesterOntology Term : 'benzo(a)pyrene metabolic pathway' added !
59196view19:07, 22 February 2013MaintBotUpdated Ensembl and UniProt data source
44980view14:26, 6 October 2011MartijnVanIerselOntology Term : 'xenobiotics biodegradation pathway' added !
44974view14:23, 6 October 2011MartijnVanIerselOntology Term : 'cellular detoxification pathway' added !
41182view23:42, 1 March 2011MaintBotRemoved redundant pathway information and comments
33411view14:49, 30 November 2009MaintBotRemoved group label
32738view23:04, 3 September 2009MaintBotModified categories
32737view23:03, 3 September 2009MaintBotwork in progress
31166view09:23, 7 August 2009Thomasremoved invalid characters from title
29866view13:14, 8 June 2009Pieter GiesbertzAdded literature reference
29509view08:23, 11 May 2009Pieter GiesbertzAdded literature references
29287view08:00, 22 April 2009Pieter GiesbertzSpecify description
29226view13:17, 15 April 2009Pieter GiesbertzSpecify description
29225view12:37, 15 April 2009Pieter GiesbertzPeriodical save, work in progress
29224view12:08, 15 April 2009Pieter GiesbertzSpecify description
29223view11:58, 15 April 2009Pieter GiesbertzSpecify description
29222view11:45, 15 April 2009Pieter GiesbertzSpecify description
29221view11:43, 15 April 2009Pieter GiesbertzNew pathway

External references

DataNodes

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NameTypeDatabase referenceComment
3-hydroxy-benzo[a]pyreneMetabolite
6-hydroxy-benzo[a]pyreneMetabolite
7,8-dihydroxy-7,8-dihydro-benzo[a]pyreneMetabolite24123 (Chemspider)
7,8-epoxy-benzo[a]pyreneMetabolite
7-hydroxy-benzo[a]pyreneMetabolite
9,10-epoxy-7,8-dihydroxy-7,8-dihydro-benzo[a]pyreneMetabolite46738 (Chemspider)
9-hydroxy-benzo[a]pyreneMetabolite
AKR1A1GeneProductENSG00000117448 (Ensembl)
AKR1C1GeneProductENSG00000187134 (Ensembl)
AKR1C2GeneProductENSG00000151632 (Ensembl)
AKR1C3GeneProductENSG00000196139 (Ensembl)
AKR1C4GeneProductENSG00000198610 (Ensembl)
Benzo[a]pyrene radical cationMetabolite
Benzo[a]pyrene-1,6-dioneMetabolite18300 (PubChem-compound)
Benzo[a]pyrene-3,6-dioneMetabolite
Benzo[a]pyrene-6,12-dioneMetabolite
Benzo[a]pyrene-7,8-dioneMetabolite105020 (PubChem-compound)
Benzo[a]pyrene-7-glucuronideMetabolite
Benzo[a]pyrene-7-sulfateMetabolite23703977 (PubChem-compound)
Benzo[a]pyrene-9-glucuronideMetabolite
Benzo[a]pyrene-9-sulfateMetabolite149850 (PubChem-compound)
Benzo[a]pyreneMetabolite2336 (PubChem-compound)
CYP1A1GeneProductENSG00000140465 (Ensembl)
CYP1B1GeneProductENSG00000138061 (Ensembl)
CYP3A4GeneProductENSG00000160868 (Ensembl)
Cytochrome P450 peroxidaseGeneProduct
EPHX1GeneProductENSG00000143819 (Ensembl)
GlucuronosyltransferaseGeneProduct
SULTGeneProduct

Annotated Interactions

No annotated interactions

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