Ligand view of benzo[a]pyrene (8392 - FMMWHPNWAFZXNH-UHFFFAOYSA-N)

C₂₀H₁₂

benzo[a]pyrene

FMMWHPNWAFZXNH-UHFFFAOYSA-N

KEGG

Chemical carcinogenesis - DNA adducts, Chemical carcinogenesis - reactive oxygen species, Chemical carcinogenesis - receptor activation, Metabolism of xenobiotics by cytochrome P450, Microbial metabolism in diverse environments

more

1.11.1.13

benzo[a]pyrene + ? = ?

657586

-

1.11.1.10

benzo[a]pyrene + Cl- + H2O2 = ?

-

benzo[a]pyrene + NADH + O2 = ?

675223

-

1.14.14.1

benzo(a)pyrene + [reduced NADPH-hemoprotein reductase] + O2 = ?

726736

-

1.14.15.1

benzo[a]pyrene + putidaredoxin + O2 = 3-hydroxybenzo[a]pyrene + oxidized putidaredoxin + H2O

-

noncompetitive

-

intratracheal instillation of benzo(a)pyrene significantly suppresses NF-kappaB translocation, sEH, thioredoxin reductase and catalase activities in lung tissue. Glycyrrhizic acid oral administration at 50 and 100 mg/kg body weight significantly shows protection of lung epithelium by suppression of caspases activities in lung tissue and reduction of total protein, total cells, elastase activity. Results indicate a strong correlation between amelioration of sEH and thioredoxin reductase activities, and NF-kappaB activation

716960

-

3.4.24.7

increases the mRNA levels of matrix metalloproteinases MMP-1, MMP-2, MMP-3, and MMP-9 in vascular smooth muscle cells and promotes the migration and invasion of cells

701317

-

3.2.1.14

0.0014

-

677514

347709

10708651

Protein engineering of cytochrome p450(cam) (CYP101) for the oxidation of polycyclic aromatic hydrocarbons

2000

Harford-Cross, C.F.; Carmichael, A.B.; Allan, F.K.; England, P.A.; Rouch, D.A.; Wong, L.L.

Protein Eng.

13

121-128

348330

11684191

Biocatalytic chlorination of aromatic hydrocarbons by chloroperoxidase of Caldariomyces fumago

2001

Vazquez-Duhalt, R.; Ayala, M.; Marquez-Rocha, F.J.

Phytochemistry

58

929-933

657586

12839767

Degradation of benzo[a]pyrene by the litter-decomposing basidiomycete Stropharia coronilla: role of manganese peroxidase

2003

Steffen, K.T.; Hatakka, A.; Hofrichter, M.

Appl. Environ. Microbiol.

69

3957-3964

660397

9050836

Unexpected genetic and structural relationships of a long-forgotten flavoenzyme to NAD(P)H:quinone reductase (DT-diaphorase)

1997

Zhao, Q.; Yang, X.L.; Holtzclaw, W.D.; Talalay, P.

Proc. Natl. Acad. Sci. USA

94

1669-1674

671921

16765324

NRH:quinone oxidoreductase 2 (NQO2) catalyzes metabolic activation of quinones and anti-tumor drugs

2006

Celli, C.M.; Tran, N.; Knox, R.; Jaiswal, A.K.

Biochem. Pharmacol.

72

366-376

673791

16545679

Nulear factor Nrf2 and antioxidant response element regulate NRH:quinone oxidoreductase 2 (NQO2) gene expression and antioxidant induction

2006

Wang, W.; Jaiswal, A.K.

Free Radic. Biol. Med.

40

1119-1130

675223

17211635

Purification, characterization, and crystallization of the components of a biphenyl dioxygenase system from Sphingobium yanoikuyae B1

2007

Yu, C.L.; Liu, W.; Ferraro, D.J.; Brown, E.N.; Parales, J.V.; Ramaswamy, S.; Zylstra, G.J.; Gibson, D.T.; Parales, R.E.

J. Ind. Microbiol. Biotechnol.

34

311-324

677514

17325822

Inhibitory analysis of the effect of polycyclic aromatic hydrocarbons on the activity of chitinase by means of liquid chromatography-mass spectrometry of chitin oligosaccharides

2007

Ooki, Y.; Kumemura, M.; Itoh, M.; Korenaga, T.

Anal. Bioanal. Chem.

387

2641-2644

701317

19022365

Benzo[a]pyrene induces expression of matrix metalloproteinases and cell migration and invasion of vascular smooth muscle cells

2009

Meng, D.; Lv, D.D.; Zhuang, X.; Sun, H.; Fan, L.; Shi, X.L.; Fang, J.

Toxicol. Lett.

184

44-49

716960

22051199

Alleviation of lung injury by glycyrrhizic acid in benzo(a)pyrene exposed rats: Probable role of soluble epoxide hydrolase and thioredoxin reductase

2011

Qamar, W.; Khan, R.; Khan, A.Q.; Rehman, M.U.; Lateef, A.; Tahir, M.; Ali, F.; Sultana, S.

Toxicology

291

25-31

726736

23416995

CYP63A2, a catalytically versatile fungal P450 monooxygenase capable of oxidizing higher-molecular-weight polycyclic aromatic hydrocarbons, alkylphenols, and alkanes

2013

Syed, K.; Porollo, A.; Lam, Y.W.; Grimmett, P.E.; Yadav, J.S.

Appl. Environ. Microbiol.

79

2692-2702

741477

29051846

Enhanced biodegradation of mixed PAHs by mutated naphthalene 1,2-dioxygenase encoded by Pseudomonas putida strain KD6 isolated from petroleum refinery waste

2017

Dutta, K.; Shityakov, S.; Das, P.P.; Ghosh, C.

3 Biotech

7

365

741711

26476651

Dihydroxylation of four- and five-ring aromatic hydrocarbons by the naphthalene dioxygenase from Sphingomonas CHY-1

2016

Jouanneau, Y.; Meyer, C.; Duraffourg, N.

Appl. Microbiol. Biotechnol.

100

1253-1263

743124

25073456

Theoretical approach to the innovative mutation of naphthalene 1,2-dioxygenase a molecular dynamics and docking study

2014

Librando, V.; Pappalardo, M.

J. Mol. Model.

20

2354

Ligand benzo[a]pyrene

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

Substrate in Enzyme-catalyzed Reactions (9 results)

Inhibitor in Enzyme-catalyzed Reactions (6 results)

Enzyme Kinetic Parameters

IC₅₀ Value (1 result)

References & Links

Literature References (14)

Links to other databases for benzo[a]pyrene

Ligand benzo[a]pyrene

Basic Ligand Information

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

Substrate in Enzyme-catalyzed Reactions (9 results)

Inhibitor in Enzyme-catalyzed Reactions (6 results)

Enzyme Kinetic Parameters

IC50 Value (1 result)

References & Links

Literature References (14)

Links to other databases for benzo[a]pyrene

IC₅₀ Value (1 result)