1,2-Naphthoquinone (BioDeep_00000010139)

 

Secondary id: BioDeep_00001871690

human metabolite blood metabolite


代谢物信息卡片


1,2-Dihydro-1,2-diketo-naphthalene

化学式: C10H6O2 (158.0367776)
中文名称: 1,2-萘醌
谱图信息: 最多检出来源 Homo sapiens(blood) 0.63%

分子结构信息

SMILES: C1=CC=C2C(=C1)C=CC(=O)C2=O
InChI: InChI=1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H

描述信息

同义名列表

9 个代谢物同义名

1,2-Dihydro-1,2-diketo-naphthalene; 1,2-Dihydronaphthalene-1,2-dione; Ortho-naphthoquinone; 1,2-Naphthalenedione; beta-Naphthoquinone; 1,2-NAPHTHOQUINONE; b-Naphthoquinone; Β-naphthoquinone; O-Naphthoquinone



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

BioCyc(1)

PlantCyc(0)

代谢反应

60 个相关的代谢反应过程信息。

Reactome(60)

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

  • Kengo Nakahara, Kyohei Hamada, Tomoki Tsuchida, Nobumasa Takasugi, Yumi Abiko, Kazuhiko Shien, Shinichi Toyooka, Yoshito Kumagai, Takashi Uehara. Covalent N-arylation by the pollutant 1,2-naphthoquinone activates the EGF receptor. The Journal of biological chemistry. 2021 Jan; 296(?):100524. doi: 10.1016/j.jbc.2021.100524. [PMID: 33705793]
  • Shuaipeng Lv, Haitao Liu, Jie Kang, Yun Luo, Ting Gong, Zhengqi Dong, Guibo Sun, Chunnian He, Xiaobo Sun, Lei Wang. Palladium-catalyzed enol/enolate directed oxidative annulation: functionalized naphthofuroquinone synthesis and bioactivity evaluation. Chemical communications (Cambridge, England). 2019 Dec; 55(98):14729-14732. doi: 10.1039/c9cc05233j. [PMID: 31690911]
  • G G N de S Wisintainer, G Scola, S Moura, T L G Lemos, C Pessoa, M O de Moraes, L G S Souza, M Roesch-Ely, J A P Henriques. O-naphthoquinone isolated from Capraria biflora L. induces selective cytotoxicity in tumor cell lines. Genetics and molecular research : GMR. 2015 Dec; 14(4):17472-81. doi: 10.4238/2015.december.21.18. [PMID: 26782390]
  • Che Lin, Dar-Ren Chen, Shu-Li Wang, Wei-Chung Hsieh, Wen-Fa Yu, Tzu-Wen Wang, Chen-His Tsai, Hz-Han Wei, Ben-Jei Tsuang, Po-Hsiung Lin. Cumulative body burdens of polycyclic aromatic hydrocarbons associated with estrogen bioactivation in pregnant women: protein adducts as biomarkers of exposure. Journal of environmental science and health. Part A, Toxic/hazardous substances & environmental engineering. 2014; 49(6):634-40. doi: 10.1080/10934529.2014.865416. [PMID: 24521408]
  • Robert F Jacob, Michael D Aleo, Yehudi Self-Medlin, Colleen M Doshna, R Preston Mason. 1,2-naphthoquinone stimulates lipid peroxidation and cholesterol domain formation in model membranes. Investigative ophthalmology & visual science. 2013 Nov; 54(12):7189-97. doi: 10.1167/iovs.13-12793. [PMID: 24130176]
  • T B Lima, O N Silva, L P Silva, T L Rocha, M F Grossi-de-Sá, O L Franco, E Leonardecz. In Vivo Effects of Cagaita (Eugenia dysenterica, DC.) Leaf Extracts on Diarrhea Treatment. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):. doi: 10.1155/2011/309390. [PMID: 20953423]
  • Soraia K P Costa, Aila Mirtes Teles, Yoshito Kumagai, Susan D Brain, Simone A Teixeira, Ana A Varriano, Maria Alice A G Barreto, Wothan Tavares de Lima, Edson Antunes, Marcelo N Muscará, Soraia K P Costa. Involvement of sensory nerves and TRPV1 receptors in the rat airway inflammatory response to two environment pollutants: diesel exhaust particles (DEP) and 1,2-naphthoquinone (1,2-NQ). Archives of toxicology. 2010 Feb; 84(2):109-17. doi: 10.1007/s00204-009-0427-x. [PMID: 19399481]
  • Po-Hsiung Lin, Dar-Ren Chen, Tzu-Wen Wang, Chia-Hua Lin, Ming-Chieh Chuang. Investigation of the cumulative tissue doses of naphthoquinones in human serum using protein adducts as biomarker of exposure. Chemico-biological interactions. 2009 Sep; 181(1):107-14. doi: 10.1016/j.cbi.2009.05.016. [PMID: 19505452]
  • Edvaldo Rodrigues de Almeida, Flávia Raquel Santos Lucena, Camilla Vila Nova Soares Silva, Wilson da Silva Costa-Junior, Jouse Bezerra Cavalcanti, Gerald Bosco Lindoso Couto, Luiz Lúcio Soares da Silva, Diógenes Luís da Mota, Alex Benício da Silveira, Samuel Daniel de Sousa Filho, Aldo Cezar Passilongo da Silva. Toxicological assessment of beta-lapachone on organs from pregnant and non-pregnant rats. Phytotherapy research : PTR. 2009 Sep; 23(9):1276-80. doi: 10.1002/ptr.2646. [PMID: 19197915]
  • Ashraf M Mahmoud, Nasr Y Khalil, Ibrahim A Darwish, Tarek Aboul-Fadl. Selective Spectrophotometric and Spectrofluorometric Methods for the Determination of Amantadine Hydrochloride in Capsules and Plasma via Derivatization with 1,2-Naphthoquinone-4-sulphonate. International journal of analytical chemistry. 2009; 2009(?):810104. doi: 10.1155/2009/810104. [PMID: 20140080]
  • Chi P Ndi, Susan J Semple, Hans J Griesser, Simon M Pyke, Mary D Barton. Antimicrobial compounds from the Australian desert plant Eremophila neglecta. Journal of natural products. 2007 Sep; 70(9):1439-43. doi: 10.1021/np070180r. [PMID: 17844993]
  • Hideaki Shimada, Misa Ohtaguro, Kazumi Miura, Yorishige Imamura. Inhibitory effects of diesel exhaust components and flavonoids on 20alpha-hydroxysteroid dehydrogenase activity in mouse tissues. Journal of enzyme inhibition and medicinal chemistry. 2007 Aug; 22(4):445-9. doi: 10.1080/14756360601162113. [PMID: 17847711]
  • Rex Munday, Barry L Smith, Christine M Munday. Structure-activity relationships in the haemolytic activity and nephrotoxicity of derivatives of 1,2- and 1,4-naphthoquinone. Journal of applied toxicology : JAT. 2007 May; 27(3):262-9. doi: 10.1002/jat.1206. [PMID: 17265417]
  • Renan Wu, Suramya Waidyanatha, Alistair P Henderson, Berrin Serdar, Yuxin Zheng, Stephen M Rappaport. Determination of dihydroxynaphthalenes in human urine by gas chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Nov; 826(1-2):206-13. doi: 10.1016/j.jchromb.2005.08.022. [PMID: 16169295]
  • Marne C Vasconcellos, Raquel C Montenegro, Gardênia C G Militão, Aluísio M Fonseca, Otília D L Pessoa, Telma L G Lemos, Cláudia Pessoa, Manoel O Moraes, Letícia V Costa-Lotufo. Bioactivity of biflorin, a typical o-naphthoquinone isolated from Capraria biflora L. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2005 May; 60(5-6):394-8. doi: 10.1515/znc-2005-5-605. [PMID: 16042338]
  • Yu-fei Dai, Shu-guang Leng, Zu-fei Pan, Stephen M Rappaport, Yu-xin Zheng. [Preliminary study on naphthalene-metabolites-albumin adduct as an exposure biomarker for coke oven workers]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine]. 2004 Nov; 38(6):392-5. doi: . [PMID: 15569511]
  • Berrin Serdar, Peter P Egeghy, Roger Gibson, Stephen M Rappaport. Dose-dependent production of urinary naphthols among workers exposed to jet fuel (JP-8). American journal of industrial medicine. 2004 Sep; 46(3):234-44. doi: 10.1002/ajim.20049. [PMID: 15307122]
  • Suramya Waidyanatha, Yuxin Zheng, Berrin Serdar, Stephen M Rappaport. Albumin adducts of naphthalene metabolites as biomarkers of exposure to polycyclic aromatic hydrocarbons. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2004 Jan; 13(1):117-24. doi: 10.1158/1055-9965.epi-03-0150. [PMID: 14744742]
  • Mary K Briggs, Emmanuel Desavis, Paula A Mazzer, R B Sunoj, Susan A Hatcher, Christopher M Hadad, Patrick G Hatcher. A new approach to evaluating the extent of Michael adduct formation to PAH quinones: tetramethylammonium hydroxide (TMAH) thermochemolysis with GC/MS. Chemical research in toxicology. 2003 Nov; 16(11):1484-92. doi: 10.1021/tx0341512. [PMID: 14615976]
  • Lidia M Lopez, Marta Dubin, Patricia H Carrizo, Mario H Burgos, Amanda Pellegrino de Iraldi, Andrés O M Stoppani. Apoptogenic effect of the lipophilic o-naphthoquinone CG 10-248 on rat hepatocytes: light and electron microscopy studies. Biocell : official journal of the Sociedades Latinoamericanas de Microscopia Electronica ... et. al. 2003 Aug; 27(2):213-24. doi: 10.32604/biocell.2003.27.213. [PMID: 14510240]
  • Huei-Ping Tzeng, Feng-Ming Ho, Kuo-Fang Chao, Min-Liang Kuo, Shoei-Yn Lin-Shiau, Shing-Hwa Liu. beta-Lapachone reduces endotoxin-induced macrophage activation and lung edema and mortality. American journal of respiratory and critical care medicine. 2003 Jul; 168(1):85-91. doi: 10.1164/rccm.200209-1051oc. [PMID: 12724123]
  • Suramya Waidyanatha, Melissa A Troester, Andrew B Lindstrom, Stephen M Rappaport. Measurement of hemoglobin and albumin adducts of naphthalene-1,2-oxide, 1,2-naphthoquinone and 1,4-naphthoquinone after administration of naphthalene to F344 rats. Chemico-biological interactions. 2002 Oct; 141(3):189-210. doi: 10.1016/s0009-2797(02)00048-0. [PMID: 12385719]
  • Jin Hee Ahn, Sung Yun Cho, Jae Du Ha, So Young Chu, Sun Ho Jung, Yoon Sung Jung, Ji Yoen Baek, In Kyung Choi, Eun Young Shin, Seung Kyu Kang, Sung Soo Kim, Hyae Gyeong Cheon, Sung-Don Yang, Joong-Kwon Choi. Synthesis and PTP1B inhibition of 1,2-naphthoquinone derivatives as potent anti-diabetic agents. Bioorganic & medicinal chemistry letters. 2002 Aug; 12(15):1941-6. doi: 10.1016/s0960-894x(02)00331-1. [PMID: 12113814]
  • T O'connor, L S Ireland, D J Harrison, J D Hayes. Major differences exist in the function and tissue-specific expression of human aflatoxin B1 aldehyde reductase and the principal human aldo-keto reductase AKR1 family members. The Biochemical journal. 1999 Oct; 343 Pt 2(?):487-504. doi: . [PMID: 10510318]
  • P Campíns Falcó, C Molins Legua, A Sevillano Cabeza, R Porras Serrano. Derivatization of amphetamine and methamphetamine with 1,2-naphthoquinone 4-sulfonic acid into solid-phase extraction cartridges. Determination of amphetamine in pharmaceutical and urine samples. The Analyst. 1997 Jul; 122(7):673-7. doi: 10.1039/a701134b. [PMID: 9330037]
  • P Campíns Falcó, C Molins Legua, R Herráez Hernandez, A Sevillano Cabeza. Improved amphetamine and methamphetamine determination in urine by normal-phase high-performance liquid chromatography with sodium 1,2-naphthoquinone 4-sulphonate as derivatizing agent and solid-phase extraction for sample clean-up. Journal of chromatography. B, Biomedical applications. 1995 Jan; 663(2):235-45. doi: 10.1016/0378-4347(94)00455-e. [PMID: 7735471]
  • T M Chan, E Chen, A Tatoyan, N S Shargill, M Pleta, P Hochstein. Stimulation of tyrosine-specific protein phosphorylation in the rat liver plasma membrane by oxygen radicals. Biochemical and biophysical research communications. 1986 Sep; 139(2):439-45. doi: 10.1016/s0006-291x(86)80010-9. [PMID: 3767971]