1,4-Naphthoquinone (BioDeep_00000000301)

 

Secondary id: BioDeep_00000017294

human metabolite blood metabolite PANOMIX_OTCML-2023


代谢物信息卡片


1,4-Dihydro-1,4-diketonaphthalene

化学式: C10H6O2 (158.0367776)
中文名称: 1,4-萘醌
谱图信息: 最多检出来源 Homo sapiens(blood) 0.09%

分子结构信息

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

描述信息

1,4-naphtoquinone, also known as 1,4-naphthalenedione or 1,4-dihydro-1,4-diketonaphthalene, is a member of the class of compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 1,4-naphtoquinone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 1,4-naphtoquinone can be synthesized from naphthalene. 1,4-naphtoquinone is also a parent compound for other transformation products, including but not limited to, 2,3-dimethoxynaphthalene-1,4-dione, alisiaquinone A, and 1,4-naphthoquinone-2-carboxylic acid. 1,4-naphtoquinone can be found in liquor, which makes 1,4-naphtoquinone a potential biomarker for the consumption of this food product. 1,4-naphtoquinone is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CONFIDENCE standard compound; INTERNAL_ID 18
1,4-Naphthoquinone is a potential pharmacophore for inhibition of both MAO (monoamine oxidase) and DNA topoisomerase activities, this latter associated with antitumor activity[1].

同义名列表

14 个代谢物同义名

1,4-Dihydro-1,4-diketonaphthalene; 1,4-dihydronaphthalene-1,4-dione; 1,4-naphthalene-dione; 1,4-Naphthalenedione; alpha-Naphthoquinone; 1,4-Naphthoquinone; [1,4]Naphthoquinon; 1,4-naphtoquinone; Α-naphthoquinone; a-naphthoquinone; p-Naphthoquinone; NAPHTHOQUINONE; Succivil; 1,4-NQ



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

6 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

  • Yukie Akutsu, Takaaki Fujiwara, Rintaro Suzuki, Yuki Nishigaya, Toshimasa Yamazaki. Juglone, a plant-derived 1,4-naphthoquinone, binds to hydroxylamine oxidoreductase and inhibits the electron transfer to cytochrome c554. Applied and environmental microbiology. 2023 Dec; 89(12):e0129123. doi: 10.1128/aem.01291-23. [PMID: 38009977]
  • Tatyana N Goleva, Konstantin G Lyamzaev, Anton G Rogov, Ljudmila S Khailova, Khoren K Epremyan, Galina P Shumakovich, Lidia V Domnina, Olga Yu Ivanova, Natalia V Marmiy, Tatiana V Zinevich, Dmitry S Esipov, Renata A Zvyagilskaya, Vladimir P Skulachev, Boris V Chernyak. Mitochondria-targeted 1,4-naphthoquinone (SkQN) is a powerful prooxidant and cytotoxic agent. Biochimica et biophysica acta. Bioenergetics. 2020 08; 1861(8):148210. doi: 10.1016/j.bbabio.2020.148210. [PMID: 32305410]
  • Daiva Majiene, Jolita Kuseliauskyte, Arturas Stimbirys, Aiste Jekabsone. Comparison of the Effect of Native 1,4-Naphthoquinones Plumbagin, Menadione, and Lawsone on Viability, Redox Status, and Mitochondrial Functions of C6 Glioblastoma Cells. Nutrients. 2019 Jun; 11(6):. doi: 10.3390/nu11061294. [PMID: 31181639]
  • Satoshi Endo, Namiki Miyagi, Toshiyuki Matsunaga, Akira Ikari. Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chemico-biological interactions. 2019 May; 305(?):12-20. doi: 10.1016/j.cbi.2019.03.026. [PMID: 30926317]
  • Małgorzata Rudnicka, Michał Ludynia, Waldemar Karcz. Effects of Naphthazarin (DHNQ) Combined with Lawsone (NQ-2-OH) or 1,4-Naphthoquinone (NQ) on the Auxin-Induced Growth of Zea mays L. Coleoptile Segments. International journal of molecular sciences. 2019 Apr; 20(7):. doi: 10.3390/ijms20071788. [PMID: 30978914]
  • Palanisamy Ravichandiran, Sivakumar Allur Subramaniyan, Seon-Young Kim, Jong-Soo Kim, Byung-Hyun Park, Kwan Seob Shim, Dong Jin Yoo. Synthesis and Anticancer Evaluation of 1,4-Naphthoquinone Derivatives Containing a Phenylaminosulfanyl Moiety. ChemMedChem. 2019 03; 14(5):532-544. doi: 10.1002/cmdc.201800749. [PMID: 30600915]
  • Pierluigi Reveglia, Sandra Savocchia, Regina Billones-Baaijens, Marco Masi, Alessio Cimmino, Antonio Evidente. Diploquinones A and B, Two New Phytotoxic Tetrasubstituted 1,4-Naphthoquinones from Diplodia mutila, a Causal Agent of Grapevine Trunk Disease. Journal of agricultural and food chemistry. 2018 Nov; 66(45):11968-11973. doi: 10.1021/acs.jafc.8b05004. [PMID: 30360617]
  • Luciana Romão, Vanessa P do Canto, Paulo A Netz, Vivaldo Moura-Neto, Ângelo C Pinto, Cristian Follmer. Conjugation with polyamines enhances the antitumor activity of naphthoquinones against human glioblastoma cells. Anti-cancer drugs. 2018 07; 29(6):520-529. doi: 10.1097/cad.0000000000000619. [PMID: 29561308]
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  • Nadia Hussein, Carla C Lopes, Paulo Castanho A Pernambuco Filho, Bruna R Carneiro, Luciano Caseli. Surface chemistry and spectroscopy studies on 1,4-naphthoquinone in cell membrane models using Langmuir monolayers. Journal of colloid and interface science. 2013 Jul; 402(?):300-6. doi: 10.1016/j.jcis.2013.04.005. [PMID: 23664393]
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  • Paul A Egan, Frank van der Kooy. Coproduction and ecological significance of naphthoquinones in carnivorous sundews (Drosera). Chemistry & biodiversity. 2012 Jun; 9(6):1033-44. doi: 10.1002/cbdv.201100274. [PMID: 22700223]
  • Duncan G G McMillan, Sophie J Marritt, Julea N Butt, Lars J C Jeuken. Menaquinone-7 is specific cofactor in tetraheme quinol dehydrogenase CymA. The Journal of biological chemistry. 2012 Apr; 287(17):14215-25. doi: 10.1074/jbc.m112.348813. [PMID: 22393052]
  • Xueyan Fu, Judith Moreines, Sarah L Booth. Vitamin K supplementation does not prevent bone loss in ovariectomized Norway rats. Nutrition & metabolism. 2012 Feb; 9(1):12. doi: 10.1186/1743-7075-9-12. [PMID: 22348311]
  • Jing Li, Lin Shen, Fu-rong Lu, You Qin, Rui Chen, Jia Li, Yan Li, Han-zi Zhan, Yuan-qiao He. Plumbagin inhibits cell growth and potentiates apoptosis in human gastric cancer cells in vitro through the NF-κB signaling pathway. Acta pharmacologica Sinica. 2012 Feb; 33(2):242-9. doi: 10.1038/aps.2011.152. [PMID: 22231395]
  • James M Brimson, Sirikalaya J Brimson, Christopher A Brimson, Varaporn Rakkhitawatthana, Tewin Tencomnao. Rhinacanthus nasutus extracts prevent glutamate and amyloid-β neurotoxicity in HT-22 mouse hippocampal cells: possible active compounds include lupeol, stigmasterol and β-sitosterol. International journal of molecular sciences. 2012; 13(4):5074-5097. doi: 10.3390/ijms13045074. [PMID: 22606031]
  • Hiromi Sato, Ryota Yamada, Midori Yanagihara, Hiroko Okuzawa, Hiroki Iwata, Ayako Kurosawa, Saki Ichinomiya, Rina Suzuki, Hiroyuki Okabe, Tomohiro Yano, Takuya Kumamoto, Noriyuki Suzuki, Tsutomu Ishikawa, Koichi Ueno. New 2-aryl-1,4-naphthoquinone-1-oxime methyl ether compound induces microtubule depolymerization and subsequent apoptosis. Journal of pharmacological sciences. 2012; 118(4):467-78. doi: 10.1254/jphs.11229fp. [PMID: 22447301]
  • Tony Hadibarata, Abdull Rahim Mohd Yusoff, Azmi Aris, Risky Ayu Kristanti. Identification of naphthalene metabolism by white rot fungus Armillaria sp. F022. Journal of environmental sciences (China). 2012; 24(4):728-32. doi: 10.1016/s1001-0742(11)60843-7. [PMID: 22894109]
  • Shin-ichiro Ozawa, Makiko Kosugi, Yasuhiro Kashino, Takashi Sugimura, Yuichiro Takahashi. 5'-monohydroxyphylloquinone is the dominant naphthoquinone of PSI in the green alga Chlamydomonas reinhardtii. Plant & cell physiology. 2012 Jan; 53(1):237-43. doi: 10.1093/pcp/pcr168. [PMID: 22138100]
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  • Leonid R Ptitsyn, Kenzo Nomura, Ilya V Sklyar, Anna B Ravcheeva. The 1,4-naphthoquinone derivative from Pyrola rotundifolia activates AMPK phosphorylation in C2C12 myotubes. Fitoterapia. 2011 Dec; 82(8):1285-9. doi: 10.1016/j.fitote.2011.09.005. [PMID: 21958969]
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