Benzo(a)pyrene metabolism (Bos taurus)

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1-7AutoxidationDNA adducts+ Reactive oxygen speciesIsomerisationDNA adducts3-hydroxy-benzo[a]pyreneAKR1C3CYP1A1AKR1A1Benzo[a]pyrene-6,12-dioneAKR1C2CYP3A4EPHX1SULTBenzo[a]pyrene-9-sulfateBenzo[a]pyrene radical cationCytochrome P450 peroxidase7,8-dihydroxy-7,8-dihydro-benzo[a]pyreneCYP1B1Benzo[a]pyrene-7-glucuronideBenzo[a]pyrene-1,6-dioneGlucuronosyltransferase9-hydroxy-benzo[a]pyreneBenzo[a]pyrene-9-glucuronide9,10-epoxy-7,8-dihydroxy-7,8-dihydro-benzo[a]pyreneBenzo[a]pyrene-7,8-dioneBenzo[a]pyrene-7-sulfateCYP1B1AKR1C47-hydroxy-benzo[a]pyreneBenzo[a]pyrene-3,6-dioneCYP1A1AKR1C16-hydroxy-benzo[a]pyreneBenzo[a]pyrene7,8-epoxy-benzo[a]pyrene


Description

Metabolism of benzo(a)pyrene, which is facilitated by CYP1A1/CYP1B1, EPHX1 and so on. Metabolism leads to formation of DNA adducts which are very carcinogenic. Also leads to formation of ROS.

Comments

HomologyConvert 
This pathway was inferred from Homo sapiens pathway WP696(72081) with a 78.0% conversion rate.

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Quality Tags

Ontology Terms

 

Bibliography

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  1. 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 Europe PMC Scholia
  2. 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 Europe PMC Scholia
  3. Malejka-Giganti D, Ritter CL; ''Peroxidative metabolism of carcinogenic N-arylhydroxamic acids: implications for tumorigenesis.''; Environ Health Perspect, 1994 PubMed Europe PMC Scholia
  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 Europe PMC Scholia
  5. Jin Y, Penning TM; ''Aldo-keto reductases and bioactivation/detoxication.''; Annu Rev Pharmacol Toxicol, 2007 PubMed Europe PMC Scholia
  6. Snyder R, Hedli CC; ''An overview of benzene metabolism.''; Environ Health Perspect, 1996 PubMed Europe PMC Scholia
  7. Luch A; ''Nature and nurture - lessons from chemical carcinogenesis.''; Nat Rev Cancer, 2005 PubMed Europe PMC Scholia

History

CompareRevisionActionTimeUserComment
97778view13:49, 7 June 2018LorasimonsModified description
89452view13:01, 15 September 2016Mkutmonremove space in ontology term id
88166view08:33, 29 July 2016Mkutmonunconnected lines
80906view15:30, 30 June 2015MkutmonNew 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
AKR1A1GeneProductENSBTAG00000000497 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = En:ENSG00000117448
AKR1C1GeneProductENSBTAG00000039356 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = En:ENSG00000187134
AKR1C2GeneProductENSBTAG00000039356 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = En:ENSG00000151632
AKR1C3GeneProductENSBTAG00000039356 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = En:ENSG00000196139
AKR1C4GeneProductENSBTAG00000039356 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = En:ENSG00000198610
Benzo[a]pyreneMetabolite
Benzo[a]pyrene radical cationMetabolite
Benzo[a]pyrene-1,6-dioneMetabolite
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-sulfateMetabolite
Benzo[a]pyrene-9-glucuronideMetabolite
Benzo[a]pyrene-9-sulfateMetabolite
CYP1A1GeneProductENSBTAG00000001021 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = En:ENSG00000140465
CYP1B1GeneProductENSBTAG00000010531 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = En:ENSG00000138061
CYP3A4GeneProductENSBTAG00000047379 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = En:ENSG00000160868
Cytochrome P450 peroxidaseGeneProduct
EPHX1GeneProductENSBTAG00000000140 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = En:ENSG00000143819
GlucuronosyltransferaseGeneProduct
SULTGeneProduct

Annotated Interactions

No annotated interactions
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