Dibenz[a,h]anthracene (BioDeep_00000009828)
Secondary id: BioDeep_00001873637
human metabolite blood metabolite Volatile Flavor Compounds
代谢物信息卡片
pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene
化学式: C22H14 (278.1095444)
中文名称: 二苯并(a,h)蒽标准溶液
谱图信息:
最多检出来源 Anoectochilus roxburghii(viridiplantae) 17.91%
分子结构信息
SMILES: C12=CC=CC=C1C3=CC(C=CC4=CC=CC=C45)=C5C=C3C=C2
InChI: InChI=1S/C22H14/c1-3-7-19-15(5-1)9-11-17-14-22-18(13-21(17)19)12-10-16-6-2-4-8-20(16)22/h1-14H
描述信息
D009676 - Noxae > D002273 - Carcinogens
Dibenz[a,h]anthracene (DBA) is a polycyclic aromatic hydrocarbon (PAH) of considerable tumorigenicity. Dibenz[a,h]anthracene results in DNA adduct formation leading to the activation of a DNA damage response. Dibenz[a,h]anthracene induces cell cycle arrest and apoptosis via both Tp53-dependent and Tp53-independent mechanisms[1][2].
同义名列表
11 个代谢物同义名
pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1,3,5,7,9,11,13,15,17,19,21-undecaene; 1,2,5,6-Dibenzanthracene, ion(1-); 1,2,5,6-Dibenzanthracene, ion(1+); 1,2,5,6-Dibenzanthracene; 1,2:5,6-Dibenzanthracene; dibenzo(a,H)Anthracene; Dibenz[a,h]anthracene; Dibenz(a,H)anthracene; Benzo[k]tetraphene; DBA; Dibenz[a,h]anthracene
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:35299
- KEGG: C14325
- PubChem: 5889
- HMDB: HMDB0251159
- Metlin: METLIN69967
- ChEMBL: CHEMBL1346946
- KNApSAcK: C00017098
- chemspider: 5678
- CAS: 53-70-3
- PMhub: MS000023647
- PubChem: 17395325
- NIKKAJI: J2.797I
- RefMet: Dibenz[a,h]anthracene
- medchemexpress: HY-W013053
- KNApSAcK: 35299
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Nettie van Meteren, Dominique Lagadic-Gossmann, Martine Chevanne, Isabelle Gallais, Dimitri Gobart, Agnès Burel, Simon Bucher, Nathalie Grova, Bernard Fromenty, Brice M R Appenzeller, Soizic Chevance, Fabienne Gauffre, Eric Le Ferrec, Odile Sergent. Polycyclic aromatic hydrocarbons can trigger hepatocyte release of extracellular vesicles by various mechanisms of action depending on their affinity for the aryl hydrocarbon receptor.
Toxicological sciences : an official journal of the Society of Toxicology.
2019 Jul; ?(?):. doi:
10.1093/toxsci/kfz157. [PMID: 31368503] - Vidya Vasudevan, K Veena Gayathri, Mary Elizabeth Gnanambal Krishnan. Bioremediation of a pentacyclic PAH, Dibenz(a,h)Anthracene- A long road to trip with bacteria, fungi, autotrophic eukaryotes and surprises.
Chemosphere.
2018 Jul; 202(?):387-399. doi:
10.1016/j.chemosphere.2018.03.074. [PMID: 29579674] - Dan-Dan Wang, Yong Liu, Na Li, Yi Zhang, Qiang Jin, Da-Cheng Hao, Hai-Long Piao, Zi-Ru Dai, Guang-Bo Ge, Ling Yang. Induction of CYP1A1 increases gefitinib-induced oxidative stress and apoptosis in A549 cells.
Toxicology in vitro : an international journal published in association with BIBRA.
2017 Oct; 44(?):36-43. doi:
10.1016/j.tiv.2017.06.022. [PMID: 28652202] - Daphnee S Pushparajah, Kathryn E Plant, Nick J Plant, Costas Ioannides. Synergistic and antagonistic interactions of binary mixtures of polycyclic aromatic hydrocarbons in the upregulation of CYP1 activity and mRNA levels in precision-cut rat liver slices.
Environmental toxicology.
2017 Mar; 32(3):764-775. doi:
10.1002/tox.22276. [PMID: 27099206] - Helmut I Padilla-Chavarría, Teobaldo R C Guizado, Andre S Pimentel. Molecular dynamics of dibenz[a,h]anthracene and its metabolite interacting with lung surfactant phospholipid bilayers.
Physical chemistry chemical physics : PCCP.
2015 Aug; 17(32):20912-22. doi:
10.1039/c5cp01443c. [PMID: 26214736] - Emelie Westberg, Ulla Hedebrant, Johanna Haglund, Tomas Alsberg, Johan Eriksson, Albrecht Seidel, Margareta Törnqvist. Conditions for sample preparation and quantitative HPLC/MS-MS analysis of bulky adducts to serum albumin with diolepoxides of polycyclic aromatic hydrocarbons as models.
Analytical and bioanalytical chemistry.
2014 Feb; 406(5):1519-30. doi:
10.1007/s00216-013-7540-7. [PMID: 24390408] - Amal I Malik, Andrea Rowan-Carroll, Andrew Williams, Christine L Lemieux, Alexandra S Long, Volker M Arlt, David H Phillips, Paul A White, Carole L Yauk. Hepatic genotoxicity and toxicogenomic responses in Muta™Mouse males treated with dibenz[a,h]anthracene.
Mutagenesis.
2013 Sep; 28(5):543-54. doi:
10.1093/mutage/get031. [PMID: 23793610] - Ling Mu, Lin Peng, Xiao-Feng Liu, Hui-Ling Bai, Jian-Qiang Zhang. [Characterization of PAHs in fly ashes from coke production].
Huan jing ke xue= Huanjing kexue.
2013 Mar; 34(3):1156-60. doi:
". [PMID: 23745428] - Grażyna Bieniek, Agnieszka Łusiak. Occupational exposure to aromatic hydrocarbons and polycyclic aromatic hydrocarbons at a coke plant.
The Annals of occupational hygiene.
2012 Aug; 56(7):796-807. doi:
10.1093/annhyg/mes016. [PMID: 22539560] - Damien Lorenzi, Jane Entwistle, Mark Cave, Joanna Wragg, John R Dean. The application of an in vitro gastrointestinal extraction to assess the oral bioaccessibility of polycyclic aromatic hydrocarbons in soils from a former industrial site.
Analytica chimica acta.
2012 Jul; 735(?):54-61. doi:
10.1016/j.aca.2012.05.030. [PMID: 22713917] - Han-Bin Huang, Ching-Huang Lai, Guan-Wen Chen, Yong-Yang Lin, Jouni J K Jaakkola, Saou-Hsing Liou, Shu-Li Wang. Traffic-related air pollution and DNA damage: a longitudinal study in Taiwanese traffic conductors.
PloS one.
2012; 7(5):e37412. doi:
10.1371/journal.pone.0037412. [PMID: 22629390] - Qin Zhao, Fang Wei, Yan-Bo Luo, Jun Ding, Neng Xiao, Yu-Qi Feng. Rapid magnetic solid-phase extraction based on magnetic multiwalled carbon nanotubes for the determination of polycyclic aromatic hydrocarbons in edible oils.
Journal of agricultural and food chemistry.
2011 Dec; 59(24):12794-800. doi:
10.1021/jf203973s. [PMID: 22103676] - Nik Veldhoen, Marek Kobylarz, Christopher J Lowe, Lizanne Meloche, Adrian M H deBruyn, Caren C Helbing. Relationship between mRNA biomarker candidates and location near a marine municipal wastewater outfall in the benthic indicator species Modiolus modiolus (L.).
Aquatic toxicology (Amsterdam, Netherlands).
2011 Sep; 105(1-2):119-26. doi:
10.1016/j.aquatox.2011.05.020. [PMID: 21703980] - Laura Campo, Silvia Fustinoni, Pieralberto Bertazzi. Quantification of carcinogenic 4- to 6-ring polycyclic aromatic hydrocarbons in human urine by solid-phase microextraction gas chromatography-isotope dilution mass spectrometry.
Analytical and bioanalytical chemistry.
2011 Aug; 401(2):625-34. doi:
10.1007/s00216-011-5110-4. [PMID: 21626187] - Jean-Jacques Sauvain, Ari Setyan, Pascal Wild, Philippe Tacchini, Grégoire Lagger, Ferdinand Storti, Simon Deslarzes, Michel Guillemin, Michel J Rossi, Michael Riediker. Biomarkers of oxidative stress and its association with the urinary reducing capacity in bus maintenance workers.
Journal of occupational medicine and toxicology (London, England).
2011 May; 6(1):18. doi:
10.1186/1745-6673-6-18. [PMID: 21619715] - O Samuel Sojinu, Oluwadayo O Sonibare, O Ekundayo, Eddy Y Zeng. Biomonitoring potentials of polycyclic aromatic hydrocarbons (PAHs) by higher plants from an oil exploration site, Nigeria.
Journal of hazardous materials.
2010 Dec; 184(1-3):759-764. doi:
10.1016/j.jhazmat.2010.08.104. [PMID: 20869163] - Yuqiang Tao, Shuchun Yao, Bin Xue, Jiancai Deng, Xiaolong Wang, Muhua Feng, Weiping Hu. Polycyclic aromatic hydrocarbons in surface sediments from drinking water sources of Taihu Lake, China: sources, partitioning and toxicological risk.
Journal of environmental monitoring : JEM.
2010 Dec; 12(12):2282-9. doi:
10.1039/c0em00144a. [PMID: 20959906] - Ana Passuello, Montse Mari, Martí Nadal, Marta Schuhmacher, José L Domingo. POP accumulation in the food chain: Integrated risk model for sewage sludge application in agricultural soils.
Environment international.
2010 Aug; 36(6):577-83. doi:
10.1016/j.envint.2010.04.015. [PMID: 20471680] - Ioana Ferecatu, Marie-Caroline Borot, Camille Bossard, Melanie Leroux, Nicole Boggetto, Francelyne Marano, Armelle Baeza-Squiban, Karine Andreau. Polycyclic aromatic hydrocarbon components contribute to the mitochondria-antiapoptotic effect of fine particulate matter on human bronchial epithelial cells via the aryl hydrocarbon receptor.
Particle and fibre toxicology.
2010 Jul; 7(?):18. doi:
10.1186/1743-8977-7-18. [PMID: 20663163] - Husam Alomirah, Sameer Al-Zenki, Adnan Husain, Wajih Sawaya, Nisar Ahmed, Bondi Gevao, Kurunthachalam Kannan. Benzo[a]pyrene and total polycyclic aromatic hydrocarbons (PAHs) levels in vegetable oils and fats do not reflect the occurrence of the eight genotoxic PAHs.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
2010 Jun; 27(6):869-78. doi:
10.1080/19440040903493793. [PMID: 20104381] - Lisa A Rodenburg, Sandra N Valle, Marta A Panero, Gabriela R Muñoz, Leslie M Shor. Mass balances on selected polycyclic aromatic hydrocarbons in the New York-New Jersey Harbor.
Journal of environmental quality.
2010 Mar; 39(2):642-53. doi:
10.2134/jeq2009.0264. [PMID: 20176837] - X B Zhou, A Cébron, T Béguiristain, C Leyval. Water and phosphorus content affect PAH dissipation in spiked soil planted with mycorrhizal alfalfa and tall fescue.
Chemosphere.
2009 Oct; 77(6):709-13. doi:
10.1016/j.chemosphere.2009.08.050. [PMID: 19775720] - Martina McGuinness, David Dowling. Plant-associated bacterial degradation of toxic organic compounds in soil.
International journal of environmental research and public health.
2009 08; 6(8):2226-47. doi:
10.3390/ijerph6082226. [PMID: 19742157] - A Bado-Nilles, C Quentel, H Thomas-Guyon, S Le Floch. Effects of two oils and 16 pure polycyclic aromatic hydrocarbons on plasmatic immune parameters in the European sea bass, Dicentrarchus labrax (Linné).
Toxicology in vitro : an international journal published in association with BIBRA.
2009 Mar; 23(2):235-41. doi:
10.1016/j.tiv.2008.12.001. [PMID: 19111921] - Nuno Ratola, Sílvia Lacorte, Damià Barceló, Arminda Alves. Microwave-assisted extraction and ultrasonic extraction to determine polycyclic aromatic hydrocarbons in needles and bark of Pinus pinaster Ait. and Pinus pinea L. by GC-MS.
Talanta.
2009 Jan; 77(3):1120-8. doi:
10.1016/j.talanta.2008.08.010. [PMID: 19064100] - Rafael Rodríguez-Acuña, María del Carmen Pérez-Camino, Arturo Cert, Wenceslao Moreda. Polycyclic aromatic hydrocarbons in spanish olive oils: relationship between benzo(a)pyrene and total polycyclic aromatic hydrocarbon content.
Journal of agricultural and food chemistry.
2008 Nov; 56(21):10428-32. doi:
10.1021/jf8016699. [PMID: 18831590] - Daphnee S Pushparajah, Meera Umachandran, Kathryn E Plant, Nick Plant, Costas Ioannides. Up-regulation of the glutathione S-transferase system in human liver by polycyclic aromatic hydrocarbons; comparison with rat liver and lung.
Mutagenesis.
2008 Jul; 23(4):299-308. doi:
10.1093/mutage/gen012. [PMID: 18388359] - Daphnee S Pushparajah, Meera Umachandran, Kathryn E Plant, Nick Plant, Costas Ioannides. Differential response of human and rat epoxide hydrolase to polycyclic aromatic hydrocarbon exposure: studies using precision-cut tissue slices.
Mutation research.
2008 Apr; 640(1-2):153-61. doi:
10.1016/j.mrfmmm.2008.01.004. [PMID: 18336844] - Hamzeh Al Zabadi, Luc Ferrari, Anne-Marie Laurent, Aziz Tiberguent, Christophe Paris, Denis Zmirou-Navier. Biomonitoring of complex occupational exposures to carcinogens: the case of sewage workers in Paris.
BMC cancer.
2008 Mar; 8(?):67. doi:
10.1186/1471-2407-8-67. [PMID: 18325085] - Kurunthachalam Kannan, Emily Perrotta. Polycyclic aromatic hydrocarbons (PAHs) in livers of California sea otters.
Chemosphere.
2008 Mar; 71(4):649-55. doi:
10.1016/j.chemosphere.2007.11.043. [PMID: 18177687] - Daphnee S Pushparajah, Meera Umachandran, Tariq Nazir, Kathryn E Plant, Nick Plant, David F V Lewis, Costas Ioannides. Up-regulation of CYP1A/B in rat lung and liver, and human liver precision-cut slices by a series of polycyclic aromatic hydrocarbons; association with the Ah locus and importance of molecular size.
Toxicology in vitro : an international journal published in association with BIBRA.
2008 Feb; 22(1):128-45. doi:
10.1016/j.tiv.2007.08.014. [PMID: 17920237] - Delia Cavallo, Cinzia L Ursini, Enrico Pira, Canzio Romano, Raffaele Maiello, Marta Petyx, Sergio Iavicoli. Evaluation of DNA damage induction on human pulmonary cells exposed to PAHs from organic extract of PM10 collected in a coke-oven plant.
Acta bio-medica : Atenei Parmensis.
2008; 79 Suppl 1(?):97-103. doi:
. [PMID: 18924315] - D Cavallo, C L Ursini, E Pira, C Romano, A Ciervo, R Maiello, A Caglieri, S Iavicoli. [In vitro study of genotoxic and oxidative effects induced on human pulmonary cells by exposure to PAHs extracted from airborne particulate matter collected in a coke plant].
Giornale italiano di medicina del lavoro ed ergonomia.
2007 Jul; 29(3 Suppl):286-7. doi:
. [PMID: 18409689] - M F Kirby, A J Smith, J Rooke, P Neall, A P Scott, I Katsiadaki. Ethoxyresorufin-O-deethylase (EROD) and vitellogenin (VTG) in flounder (Platichthys flesus): system interaction, crosstalk and implications for monitoring.
Aquatic toxicology (Amsterdam, Netherlands).
2007 Mar; 81(3):233-44. doi:
10.1016/j.aquatox.2006.12.004. [PMID: 17239453] - S C Corgié, T Beguiristain, C Leyval. Differential composition of bacterial communities as influenced by phenanthrene and dibenzo[a,h]anthracene in the rhizosphere of ryegrass (Lolium perenne L.).
Biodegradation.
2006 Dec; 17(6):511-21. doi:
10.1007/s10532-005-9022-x. [PMID: 16485083] - M Fontcuberta, J F Arqués, M Martínez, A Suárez, J R Villalbí, F Centrich, E Serrahima, J Duran, C Casas. Polycyclic aromatic hydrocarbons in food samples collected in Barcelona, Spain.
Journal of food protection.
2006 Aug; 69(8):2024-8. doi:
10.4315/0362-028x-69.8.2024. [PMID: 16924937] - Howard W Mielke, Guangdi Wang, Christopher R Gonzales, Eric T Powell, Bin Le, V Nancy Quach. PAHs and metals in the soils of inner-city and suburban New Orleans, Louisiana, USA.
Environmental toxicology and pharmacology.
2004 Dec; 18(3):243-7. doi:
10.1016/j.etap.2003.11.011. [PMID: 21782755] - Luisa R Bordajandi, Gema Gómez, Esteban Abad, Josep Rivera, María Del Mar Fernández-Bastón, Julián Blasco, María José González. Survey of persistent organochlorine contaminants (PCBs, PCDD/Fs, and PAHs), heavy metals (Cu, Cd, Zn, Pb, and Hg), and arsenic in food samples from Huelva (Spain): levels and health implications.
Journal of agricultural and food chemistry.
2004 Feb; 52(4):992-1001. doi:
10.1021/jf030453y. [PMID: 14969562] - Jackie Schroder, Nicholas Basta, Mark Payton, James Wilson, Ruth Carlson, David Janz, Robert Lochmiller. Ecotoxicological risks associated with land treatment of petrochemical wastes. I. Residual soil contamination and bioaccumulation by cotton rats (Sigmodon hispidus).
Journal of toxicology and environmental health. Part A.
2003 Feb; 66(4):305-25. doi:
10.1080/15287390306365. [PMID: 12554539] - K A Fähnrich, M Pravda, G G Guilbault. Disposable amperometric immunosensor for the detection of polycyclic aromatic hydrocarbons (PAHs) using screen-printed electrodes.
Biosensors & bioelectronics.
2003 Jan; 18(1):73-82. doi:
10.1016/s0956-5663(02)00112-4. [PMID: 12445447] - Junfeng Niu, Jingwen Chen, Dieter Martens, Xie Quan, Fenglin Yang, Antonius Kettrup, Karl Werner Schramm. Photolysis of polycyclic aromatic hydrocarbons adsorbed on spruce [Picea abies (L) Karst] needles under sunlight irradiation.
Environmental pollution (Barking, Essex : 1987).
2003; 123(1):39-45. doi:
10.1016/s0269-7491(02)00362-7. [PMID: 12663204] - Donghui Li, Mianying Wang, Pervez Firoz Firozi, Ping Chang, Weiqing Zhang, Wanda Baer-Dubowska, Bhagavatula Moorthy, Suryanarayana V Vulimiri, Regine Goth-Goldstein, Eric H Weyand, John DiGiovanni. Characterization of a major aromatic DNA adduct detected in human breast tissues.
Environmental and molecular mutagenesis.
2002; 39(2-3):193-200. doi:
10.1002/em.10063. [PMID: 11921189] - A Perico, M Gottardi, V Boddi, P Bavazzano, E Lanciotti. Assessment of exposure to polycyclic aromatic hydrocarbons in police in Florence, Italy, through personal air sampling and biological monitoring of the urinary metabolite 1-hydroxypyrene.
Archives of environmental health.
2001 Nov; 56(6):506-12. doi:
10.1080/00039890109602899. [PMID: 11958550] - E J Joner, A Johansen, A P Loibner, M A de la Cruz, O H Szolar, J M Portal, C Leyval. Rhizosphere effects on microbial community structure and dissipation and toxicity of polycyclic aromatic hydrocarbons (PAHs) in spiked soil.
Environmental science & technology.
2001 Jul; 35(13):2773-7. doi:
10.1021/es000288s. [PMID: 11452608] - J Szaniszló, G Ungváry. Polycyclic aromatic hydrocarbon exposure and burden of outdoor workers in Budapest.
Journal of toxicology and environmental health. Part A.
2001 Mar; 62(5):297-306. doi:
10.1080/152873901300017995. [PMID: 11261893] - S Li, D Pan, G Wang. Analysis of polycyclic aromatic hydrocarbons in cooking oil fumes.
Archives of environmental health.
1994 Mar; 49(2):119-22. doi:
10.1080/00039896.1994.9937464. [PMID: 8161241]