2-((2E)-3,7-Dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl-1,4-benzenediol (BioDeep_00000014409)

   


代谢物信息卡片


2-((2E)-3,7-Dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl-1,4-benzenediol

  化学式: C19H28O4 (320.1987)
中文名称:
  谱图信息: 最多检出来源 Homo sapiens(endogenous) 0.87%

分子结构信息

SMILES: CC1=C(C(=C(C(=C1O)OC)OC)O)CC=C(C)CCC=C(C)C
InChI: InChI=1S/C19H28O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10,20-21H,7,9,11H2,1-6H3/b13-10+


描述信息

同义名列表

1 个代谢物同义名

2-((2E)-3,7-Dimethyl-2,6-octadienyl)-5,6-dimethoxy-3-methyl-1,4-benzenediol



数据库引用编号

4 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome()

BioCyc(4)

PlantCyc()

代谢反应

56 个相关的代谢反应过程信息。

Reactome()

BioCyc(12)

WikiPathways()

Plant Reactome()

INOH(2)

PlantCyc()

COVID-19 Disease Map()

PathBank(42)

PharmGKB()

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。

亚细胞结构定位 关联基因列表


文献列表

  • Yoshio Suzuki, Shunsuke Nagato, Keishoku Sakuraba, Katsuya Morio, Keisuke Sawaki. Short-term ubiquinol-10 supplementation alleviates tissue damage in muscle and fatigue caused by strenuous exercise in male distance runners. International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition. 2021 Jun; 91(3-4):261-270. doi: 10.1024/0300-9831/a000627. [PMID: 32003645]
  • Kazuo Mukai, Yasuhiro Maruoka, Saya Kitagaki, Shin-Ichi Nagaoka. Finding of Remarkable Synergistic Effect on the Aroxyl-Radical-Scavenging Rates (ks) under the Coexistence of Vitamin E Homologues (or Vegetable Oils) and Ubiquinol-10: Proposal of A New Mechanism to Explain An Increase of ks Value. Journal of oleo science. 2020 Oct; 69(10):1241-1255. doi: 10.5650/jos.ess20091. [PMID: 32908095]
  • Kei Mizuno, Akihiro T Sasaki, Kyosuke Watanabe, Yasuyoshi Watanabe. Ubiquinol-10 Intake Is Effective in Relieving Mild Fatigue in Healthy Individuals. Nutrients. 2020 Jun; 12(6):. doi: 10.3390/nu12061640. [PMID: 32498248]
  • Takayuki Takahashi, Yukitoshi Mine, Tadashi Okamoto. Extracellular coenzyme Q10 (CoQ10) is reduced to ubiquinol-10 by intact Hep G2 cells independent of intracellular CoQ10 reduction. Archives of biochemistry and biophysics. 2019 09; 672(?):108067. doi: 10.1016/j.abb.2019.108067. [PMID: 31400302]
  • Kyosuke Watanabe, Satoshi Nozaki, Miki Goto, Ken-Ichi Kaneko, Emi Hayashinaka, Satsuki Irie, Akira Nishiyama, Kazuaki Kasai, Kenji Fujii, Yasuhiro Wada, Kei Mizuno, Kenji Mizuseki, Hisashi Doi, Yasuyoshi Watanabe. PET imaging of 11C-labeled coenzyme Q10: Comparison of biodistribution between [11C]ubiquinol-10 and [11C]ubiquinone-10. Biochemical and biophysical research communications. 2019 05; 512(3):611-615. doi: 10.1016/j.bbrc.2019.03.073. [PMID: 30914201]
  • Sho Suzuki, Takuji Gotoda, Chika Kusano, Hisatomo Ikehara, Yo Miyakoshi, Kenji Fujii. Effect of Ubiquinol Intake on Defecation Frequency and Stool Form: A Prospective, Double-Blinded, Randomized Control Study. Journal of medicinal food. 2019 Jan; 22(1):81-86. doi: 10.1089/jmf.2018.4233. [PMID: 30192695]
  • Danilo Wilhelm-Filho, César G Fraga, Alberto Boveris. Seasonal and ontogenetic changes modulate oxygen consumption and antioxidant defenses in the cutlassfish Trichiurus lepturus (Pisces, Trichiuridae). Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2017 Sep; 199(?):90-97. doi: 10.1016/j.cbpc.2017.03.013. [PMID: 28347745]
  • A Kolusari, A Cebi, E Akgun, H H Alp, E Bakan. May supplementation of coenzyme Q10 help prevent development of hydatidiform mole?. Clinical and experimental obstetrics & gynecology. 2017; 44(3):398-402. doi: ". [PMID: 29949281]
  • Kazuhiko Matsuo, Kazuaki Kasai, Kazunori Hosoe, Iwao Funahashi. Stability of ubiquinol-10 (reduced form of coenzyme Q10 ) in human blood. Biomedical chromatography : BMC. 2016 Apr; 30(4):500-2. doi: 10.1002/bmc.3570. [PMID: 26248527]
  • Simone Onur, Petra Niklowitz, Alexandra Fischer, Gunnar Jacobs, Wolfgang Lieb, Matthias Laudes, Thomas Menke, Frank Döring. Determination of the coenzyme Q10 status in a large Caucasian study population. BioFactors (Oxford, England). 2015 Jul; 41(4):211-21. doi: 10.1002/biof.1216. [PMID: 26228113]
  • Qin Zhao, Chi-Tang Ho, Qingrong Huang. Effect of ubiquinol-10 on citral stability and off-flavor formation in oil-in-water (O/W) nanoemulsions. Journal of agricultural and food chemistry. 2013 Aug; 61(31):7462-9. doi: 10.1021/jf4017527. [PMID: 23855652]
  • Kazuo Mukai, Aya Ouchi, Saori Nakaya, Shin-ichi Nagaoka. Aroxyl-radical-scavenging rate increases remarkably under the coexistence of α-tocopherol and ubiquinol-10 (or vitamin C): finding of synergistic effect on the reaction rate. The journal of physical chemistry. B. 2013 Jul; 117(28):8378-91. doi: 10.1021/jp403239q. [PMID: 23777398]
  • Jacopo Lucchetti, Marianna Marino, Simonetta Papa, Massimo Tortarolo, Giovanna Guiso, Silvia Pozzi, Valentina Bonetto, Silvio Caccia, Ettore Beghi, Caterina Bendotti, Marco Gobbi. A mouse model of familial ALS has increased CNS levels of endogenous ubiquinol9/10 and does not benefit from exogenous administration of ubiquinol10. PloS one. 2013; 8(7):e69540. doi: 10.1371/journal.pone.0069540. [PMID: 23936040]
  • Takako Miyamae, Manabu Seki, Tomoko Naga, Shinya Uchino, Haruki Asazuma, Takuma Yoshida, Yuki Iizuka, Masako Kikuchi, Tomoyuki Imagawa, Yutaka Natsumeda, Shumpei Yokota, Yorihiro Yamamoto. Increased oxidative stress and coenzyme Q10 deficiency in juvenile fibromyalgia: amelioration of hypercholesterolemia and fatigue by ubiquinol-10 supplementation. Redox report : communications in free radical research. 2013; 18(1):12-9. doi: 10.1179/1351000212y.0000000036. [PMID: 23394493]
  • Kazuo Mukai, Masanori Oi, Aya Ouchi, Shin-ichi Nagaoka. Kinetic study of the α-tocopherol-regeneration reaction of ubiquinol-10 in methanol and acetonitrile solutions: notable effect of the alkali and alkaline earth metal salts on the reaction rates. The journal of physical chemistry. B. 2012 Mar; 116(8):2615-21. doi: 10.1021/jp2118086. [PMID: 22316107]
  • Sophie A Weiss, Richard J Bushby, Stephen D Evans, Lars J C Jeuken. A study of cytochrome bo3 in a tethered bilayer lipid membrane. Biochimica et biophysica acta. 2010 Dec; 1797(12):1917-23. doi: 10.1016/j.bbabio.2010.01.012. [PMID: 20096262]
  • Amr A Fouad, Ali Ibrahim Al-Sultan, Shereen M Refaie, Mohamed T Yacoubi. Coenzyme Q10 treatment ameliorates acute cisplatin nephrotoxicity in mice. Toxicology. 2010 Jul; 274(1-3):49-56. doi: 10.1016/j.tox.2010.05.007. [PMID: 20510337]
  • Kazuo Mukai, Aiko Tokunaga, Shingo Itoh, Yu Kanesaki, Aya Ouchi, Keishi Ohara, Shin-ichi Nagaoka, Kouichi Abe. Comparison between the free-radical-scavenging activities with vitamin E and ubiquinol in biological systems based on their reaction rates: a research account. BioFactors (Oxford, England). 2008; 32(1-4):49-58. doi: 10.1002/biof.5520320107. [PMID: 19096100]
  • Rosamaria Fiorini, Letizia Ragni, Simona Ambrosi, Gian Paolo Littarru, Enrico Gratton, Theodore Hazlett. Fluorescence studies of the interactions of ubiquinol-10 with liposomes. Photochemistry and photobiology. 2008 Jan; 84(1):209-14. doi: 10.1111/j.1751-1097.2007.00221.x. [PMID: 18173722]
  • J Ruiz-Jiménez, F Priego-Capote, J M Mata-Granados, J M Quesada, M D Luque de Castro. Determination of the ubiquinol-10 and ubiquinone-10 (coenzyme Q10) in human serum by liquid chromatography tandem mass spectrometry to evaluate the oxidative stress. Journal of chromatography. A. 2007 Dec; 1175(2):242-8. doi: 10.1016/j.chroma.2007.10.055. [PMID: 17996879]
  • Pavla Záková, Roman Kand'ár, Lucie Skarydová, Jirí Skalický, Andrej Myjavec, Petr Vojtísek. Ubiquinol-10/lipids ratios in consecutive patients with different angiographic findings. Clinica chimica acta; international journal of clinical chemistry. 2007 May; 380(1-2):133-8. doi: 10.1016/j.cca.2007.01.025. [PMID: 17336955]
  • Kazuo Mukai, Aiko Tokunaga, Shingo Itoh, Yu Kanesaki, Keishi Ohara, Shin-Ichi Nagaoka, Kouichi Abe. Structure-activity relationship of the free-radical-scavenging reaction by vitamin E (alpha-, beta-, gamma-, delta-Tocopherols) and ubiquinol-10: pH dependence of the reaction rates. The journal of physical chemistry. B. 2007 Jan; 111(3):652-62. doi: 10.1021/jp0650580. [PMID: 17228924]
  • Akimichi Asano, Junji Kobayashi, Yuko Murase, Atsushi Nohara, Masa-Aki Kawashiri, Akihiro Inazu, Masami Shimizu, Hiroshi Mabuchi. Effects of fenofibrate therapy on plasma ubiquinol-10 and ubiquinone-10 levels in Japanese patients with hyperlipidemia and type 2 diabetes mellitus. Pharmacotherapy. 2006 Apr; 26(4):447-51. doi: 10.1592/phco.26.4.447. [PMID: 16553501]
  • Hiroshi Mabuchi, Toshinori Higashikata, Masaaki Kawashiri, Shoji Katsuda, Mihoko Mizuno, Atsushi Nohara, Akihiro Inazu, Junji Koizumi, Junji Kobayashi. Reduction of serum ubiquinol-10 and ubiquinone-10 levels by atorvastatin in hypercholesterolemic patients. Journal of atherosclerosis and thrombosis. 2005; 12(2):111-9. doi: 10.5551/jat.12.111. [PMID: 15942122]
  • Lucas Actis-Goretta, Fernando Carrasquedo, Cesar G Fraga. The regular supplementation with an antioxidant mixture decreases oxidative stress in healthy humans. Gender effect. Clinica chimica acta; international journal of clinical chemistry. 2004 Nov; 349(1-2):97-103. doi: 10.1016/j.cccn.2004.06.009. [PMID: 15469861]
  • Ligia F Gomes, André F Alves, Alex Sevanian, Clóvis de Araújo Peres, Maysa S Cendoroglo, Clineu de Mello-Almada, Lara M Quirino, Luiz R Ramos, Virgínia B C Junqueira. Role of beta2-glycoprotein I, LDL-, and antioxidant levels in hypercholesterolemic elderly subjects. Antioxidants & redox signaling. 2004 Apr; 6(2):237-44. doi: 10.1089/152308604322899305. [PMID: 15025925]
  • M Cristina Polidori, Patrizia Mecocci, Mark Levine, Balz Frei. Short-term and long-term vitamin C supplementation in humans dose-dependently increases the resistance of plasma to ex vivo lipid peroxidation. Archives of biochemistry and biophysics. 2004 Mar; 423(1):109-15. doi: 10.1016/j.abb.2003.12.019. [PMID: 14871474]
  • Michael V Miles, Paul S Horn, John A Morrison, Peter H Tang, Ton DeGrauw, Amadeo J Pesce. Plasma coenzyme Q10 reference intervals, but not redox status, are affected by gender and race in self-reported healthy adults. Clinica chimica acta; international journal of clinical chemistry. 2003 Jun; 332(1-2):123-32. doi: 10.1016/s0009-8981(03)00137-2. [PMID: 12763289]
  • Ling Xia, Tomas Nordman, Jerker M Olsson, Anastassios Damdimopoulos, Linda Björkhem-Bergman, Ivan Nalvarte, Lennart C Eriksson, Elias S J Arnér, Giannis Spyrou, Mikael Björnstedt. The mammalian cytosolic selenoenzyme thioredoxin reductase reduces ubiquinone. A novel mechanism for defense against oxidative stress. The Journal of biological chemistry. 2003 Jan; 278(4):2141-6. doi: 10.1074/jbc.m210456200. [PMID: 12435734]
  • Y Yamamoto. Role of active oxygen species and antioxidants in photoaging. Journal of dermatological science. 2001 Aug; 27 Suppl 1(?):S1-4. doi: 10.1016/s0923-1811(01)00120-7. [PMID: 11514118]
  • J Plat, R P Mensink. Effects of diets enriched with two different plant stanol ester mixtures on plasma ubiquinol-10 and fat-soluble antioxidant concentrations. Metabolism: clinical and experimental. 2001 May; 50(5):520-9. doi: 10.1053/meta.2001.22509. [PMID: 11319712]
  • M C Polidori, P Mecocci, B Frei. Plasma vitamin C levels are decreased and correlated with brain damage in patients with intracranial hemorrhage or head trauma. Stroke. 2001 Apr; 32(4):898-902. doi: 10.1161/01.str.32.4.898. [PMID: 11283389]
  • T Menke, P Niklowitz, S Adam, M Weber, B Schlüter, W Andler. Simultaneous detection of ubiquinol-10, ubiquinone-10, and tocopherols in human plasma microsamples and macrosamples as a marker of oxidative damage in neonates and infants. Analytical biochemistry. 2000 Jul; 282(2):209-17. doi: 10.1006/abio.2000.4579. [PMID: 10873275]
  • C Perugini, M Bagnati, C Cau, R Bordone, E Zoppis, P Paffoni, R Re, E Albano, G Bellomo. Distribution of lipid-soluble antioxidants in lipoproteins from healthy subjects. I. Correlation with plasma antioxidant levels and composition of lipoproteins. Pharmacological research. 2000 Jan; 41(1):55-65. doi: NULL. [PMID: 10600270]
  • T Okamoto, K Mizuta, S Mizobuchi, A Usui, T Takahashi, S Fujimoto, T Kishi. Decreased serum ubiquinol-10 levels in healthy subjects during exercise at maximal oxygen uptake. BioFactors (Oxford, England). 2000; 11(1-2):31-3. doi: 10.1002/biof.5520110109. [PMID: 10705954]
  • F Lucesoli, M Caligiuri, M F Roberti, J C Perazzo, C G Fraga. Dose-dependent increase of oxidative damage in the testes of rats subjected to acute iron overload. Archives of biochemistry and biophysics. 1999 Dec; 372(1):37-43. doi: 10.1006/abbi.1999.1476. [PMID: 10562414]
  • M Tomasetti, G P Littarru, R Stocker, R Alleva. Coenzyme Q10 enrichment decreases oxidative DNA damage in human lymphocytes. Free radical biology & medicine. 1999 Nov; 27(9-10):1027-32. doi: 10.1016/s0891-5849(99)00132-x. [PMID: 10569635]
  • E M de Cavanagh, L Ferder, F Carrasquedo, D Scrivo, A Wassermann, C G Fraga, F Inserra. Higher levels of antioxidant defenses in enalapril-treated versus non-enalapril-treated hemodialysis patients. American journal of kidney diseases : the official journal of the National Kidney Foundation. 1999 Sep; 34(3):445-55. doi: 10.1016/s0272-6386(99)70071-5. [PMID: 10469854]
  • K Hara, S Yamashita, A Fujisawa, S Ishiwa, T Ogawa, Y Yamamoto. Oxidative stress in newborn infants with and without asphyxia as measured by plasma antioxidants and free fatty acids. Biochemical and biophysical research communications. 1999 Apr; 257(1):244-8. doi: 10.1006/bbrc.1999.0436. [PMID: 10092541]
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  • A Kontush, S Schippling, T Spranger, U Beisiegel. Plasma ubiquinol-10 as a marker for disease: is the assay worthwhile?. BioFactors (Oxford, England). 1999; 9(2-4):225-9. doi: 10.1002/biof.5520090217. [PMID: 10416034]
  • B Finckh, A Kontush, J Commentz, C Hübner, M Burdelski, A Kohlschütter. High-performance liquid chromatography-coulometric electrochemical detection of ubiquinol 10, ubiquinone 10, carotenoids, and tocopherols in neonatal plasma. Methods in enzymology. 1999; 299(?):341-8. doi: 10.1016/s0076-6879(99)99034-1. [PMID: 9916213]
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  • R Alleva, A Scararmucci, F Mantero, S Bompadre, L Leoni, G P Littarru. The protective role of ubiquinol-10 against formation of lipid hydroperoxides in human seminal fluid. Molecular aspects of medicine. 1997; 18 Suppl(?):S221-8. doi: 10.1016/s0098-2997(97)00040-x. [PMID: 9266525]
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