1,2,4-BENZENETRIOL (BioDeep_00001868243)

Main id: BioDeep_00000003216

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


1,2,4-Trihydroxybenzene

化学式: C6H6O3 (126.0316926)
中文名称: 1,2,4-苯三酚
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=C(C=C1O)O)O
InChI: InChI=1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H

描述信息

A benzenetriol carrying hydroxy groups at positions 1, 2 and 4.
1,2,4-Trihydroxybenzene (Hydroxyhydroquinone), a by-product of coffee bean roasting, increases intracellular Ca2+ concentration in rat thymic lymphocytes[1].
1,2,4-Trihydroxybenzene (Hydroxyhydroquinone), a by-product of coffee bean roasting, increases intracellular Ca2+ concentration in rat thymic lymphocytes[1].

同义名列表

5 个代谢物同义名

1,2,4-Trihydroxybenzene; Benzene-1,2,4-triol; 1,2,4-BENZENETRIOL; Benzene-1,2,4-triol; 1,2,4-Benzenetriol



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(8)

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)

38 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

  • Masato Kajikawa, Tatsuya Maruhashi, Takayuki Hidaka, Yukiko Nakano, Satoshi Kurisu, Takeshi Matsumoto, Yumiko Iwamoto, Shinji Kishimoto, Shogo Matsui, Yoshiki Aibara, Farina Mohamad Yusoff, Yasuki Kihara, Kazuaki Chayama, Chikara Goto, Kensuke Noma, Ayumu Nakashima, Takuya Watanabe, Hiroshi Tone, Masanobu Hibi, Noriko Osaki, Yoshihisa Katsuragi, Yukihito Higashi. Coffee with a high content of chlorogenic acids and low content of hydroxyhydroquinone improves postprandial endothelial dysfunction in patients with borderline and stage 1 hypertension. European journal of nutrition. 2019 Apr; 58(3):989-996. doi: 10.1007/s00394-018-1611-7. [PMID: 29330659]
  • Keiko Ishida, Koichi Misawa, Masaki Yamamoto, Akira Shimotoyodome. Hydroxyhydroquinone impairs fat utilization in mice by reducing nitric oxide availability. The journal of physiological sciences : JPS. 2018 Nov; 68(6):855-864. doi: 10.1007/s12576-018-0605-9. [PMID: 29572772]
  • Shun Katada, Takuya Watanabe, Tomohito Mizuno, Shinichi Kobayashi, Masao Takeshita, Noriko Osaki, Shigeru Kobayashi, Yoshihisa Katsuragi. Effects of Chlorogenic Acid-Enriched and Hydroxyhydroquinone-Reduced Coffee on Postprandial Fat Oxidation and Antioxidative Capacity in Healthy Men: A Randomized, Double-Blind, Placebo-Controlled, Crossover Trial. Nutrients. 2018 Apr; 10(4):. doi: 10.3390/nu10040525. [PMID: 29690626]
  • Takeshi Kodama, Takuya Ito, Dya Fita Dibwe, So-Yeun Woo, Hiroyuki Morita. Syntheses of benzophenone-xanthone hybrid polyketides and their antibacterial activities. Bioorganic & medicinal chemistry letters. 2017 06; 27(11):2397-2400. doi: 10.1016/j.bmcl.2017.04.017. [PMID: 28416134]
  • Liya Li, Navindra P Seeram. Further investigation into maple syrup yields 3 new lignans, a new phenylpropanoid, and 26 other phytochemicals. Journal of agricultural and food chemistry. 2011 Jul; 59(14):7708-16. doi: 10.1021/jf2011613. [PMID: 21675726]
  • Masood Sadiq Butt, M Tauseef Sultan. Coffee and its consumption: benefits and risks. Critical reviews in food science and nutrition. 2011 Apr; 51(4):363-73. doi: 10.1080/10408390903586412. [PMID: 21432699]
  • Ryuji Ochiai, Akiro Chikama, Kiyoshi Kataoka, Ichiro Tokimitsu, Yoshihiro Maekawa, Mitsuru Ohishi, Hiromi Rakugi, Hiroshi Mikami. Effects of hydroxyhydroquinone-reduced coffee on vasoreactivity and blood pressure. Hypertension research : official journal of the Japanese Society of Hypertension. 2009 Nov; 32(11):969-74. doi: 10.1038/hr.2009.132. [PMID: 19713967]
  • Kuo-Ching Jan, Chi-Tang Ho, Lucy Sun Hwang. Elimination and metabolism of sesamol, a bioactive compound in sesame oil, in rats. Molecular nutrition & food research. 2009 May; 53 Suppl 1(?):S36-43. doi: 10.1002/mnfr.200800214. [PMID: 19156718]
  • Lei Wang, Xuanzhen Jiang. Unusual catalytic effects of iron salts on phenol degradation by glow discharge plasma in aqueous solution. Journal of hazardous materials. 2009 Jan; 161(2-3):926-32. doi: 10.1016/j.jhazmat.2008.04.037. [PMID: 18501506]
  • Atsushi Suzuki, Akihiko Fujii, Hiroko Jokura, Ichiro Tokimitsu, Tadashi Hase, Ikuo Saito. Hydroxyhydroquinone interferes with the chlorogenic acid-induced restoration of endothelial function in spontaneously hypertensive rats. American journal of hypertension. 2008 Jan; 21(1):23-7. doi: 10.1038/ajh.2007.3. [PMID: 18091740]
  • Samia Ammar, Mohamed Ali Mahjoub, Nesrine Charfi, Ines Skandarani, Leila Chekir-Ghedira, Zine Mighri. Mutagenic, antimutagenic and antioxidant activities of a new class of beta-glucoside hydroxyhydroquinone from Anagallis monelli growing in Tunisia. Chemical & pharmaceutical bulletin. 2007 Mar; 55(3):385-8. doi: 10.1248/cpb.55.385. [PMID: 17329877]
  • Ignasi Sirés, Conchita Arias, Pere Lluís Cabot, Francesc Centellas, José Antonio Garrido, Rosa María Rodríguez, Enric Brillas. Degradation of clofibric acid in acidic aqueous medium by electro-Fenton and photoelectro-Fenton. Chemosphere. 2007 Jan; 66(9):1660-9. doi: 10.1016/j.chemosphere.2006.07.039. [PMID: 16938340]
  • Mingxiang Liang, Elizabeth Davis, Dale Gardner, Xiaoning Cai, Yajun Wu. Involvement of AtLAC15 in lignin synthesis in seeds and in root elongation of Arabidopsis. Planta. 2006 Oct; 224(5):1185-96. doi: 10.1007/s00425-006-0300-6. [PMID: 16779554]
  • Anna C Fick, Uwe M Reinscheid. Characterization of the binding epitope of ciprofloxacin bound to human serum albumin. Journal of pharmaceutical and biomedical analysis. 2006 Jun; 41(3):1025-8. doi: 10.1016/j.jpba.2006.01.023. [PMID: 16497464]
  • Xiaoning Cai, Elizabeth J Davis, Jenny Ballif, Mingxiang Liang, Emily Bushman, Victor Haroldsen, Javad Torabinejad, Yajun Wu. Mutant identification and characterization of the laccase gene family in Arabidopsis. Journal of experimental botany. 2006; 57(11):2563-9. doi: 10.1093/jxb/erl022. [PMID: 16804053]
  • Motoyuki Shimizu, Yoshinori Kobayashi, Hiroo Tanaka, Hiroyuki Wariishi. Transportation mechanism for vanillin uptake through fungal plasma membrane. Applied microbiology and biotechnology. 2005 Sep; 68(5):673-9. doi: 10.1007/s00253-005-1933-2. [PMID: 15868144]
  • Barry Halliwell, Lee Hua Long, Tsin Pinn Yee, Sharon Lim, Ronan Kelly. Establishing biomarkers of oxidative stress: the measurement of hydrogen peroxide in human urine. Current medicinal chemistry. 2004 May; 11(9):1085-92. doi: 10.2174/0929867043365404. [PMID: 15134507]
  • Suramya Waidyanatha, Nathaniel Rothman, Guilan Li, Martyn T Smith, Songnian Yin, Stephen M Rappaport. Rapid determination of six urinary benzene metabolites in occupationally exposed and unexposed subjects. Analytical biochemistry. 2004 Apr; 327(2):184-99. doi: 10.1016/j.ab.2004.01.008. [PMID: 15051535]
  • Ryszard Jankowiak, Yuri Markushin, Ercole L Cavalieri, Gerald J Small. Spectroscopic characterization of the 4-hydroxy catechol estrogen quinones-derived GSH and N-acetylated Cys conjugates. Chemical research in toxicology. 2003 Mar; 16(3):304-11. doi: 10.1021/tx020088p. [PMID: 12641430]
  • Sergio Gómez-Alonso, Giuseppe Fregapane, M Desamparados Salvador, Michael H Gordon. Changes in phenolic composition and antioxidant activity of virgin olive oil during frying. Journal of agricultural and food chemistry. 2003 Jan; 51(3):667-72. doi: 10.1021/jf025932w. [PMID: 12537439]
  • Kazuyuki Hiramoto, Tomoko Kida, Kiyomi Kikugawa. Increased urinary hydrogen peroxide levels caused by coffee drinking. Biological & pharmaceutical bulletin. 2002 Nov; 25(11):1467-71. doi: 10.1248/bpb.25.1467. [PMID: 12419961]
  • H Mi, K Hiramoto, K Kujirai, K Ando, Y Ikarashi, K Kikugawa. Effect of food reductones, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and hydroxyhydroquinone (HHQ), on lipid peroxidation and type IV and I allergy responses of mouse. Journal of agricultural and food chemistry. 2001 Oct; 49(10):4950-5. doi: 10.1021/jf010556l. [PMID: 11600049]
  • Q Qu, A A Melikian, G Li, R Shore, L Chen, B Cohen, S Yin, M R Kagan, H Li, M Meng, X Jin, W Winnik, Y Li, R Mu, K Li. Validation of biomarkers in humans exposed to benzene: urine metabolites. American journal of industrial medicine. 2000 May; 37(5):522-31. doi: 10.1002/(sici)1097-0274(200005)37:5<522::aid-ajim8>3.0.co;2-g. [PMID: 10723046]
  • Y Shen, H M Shen, C Y Shi, C N Ong. Benzene metabolites enhance reactive oxygen species generation in HL60 human leukemia cells. Human & experimental toxicology. 1996 May; 15(5):422-7. doi: 10.1177/096032719601500510. [PMID: 8735467]
  • P C Kuo, K Y Abe. Interleukin 1-induced production of nitric oxide inhibits benzenetriol-mediated oxidative injury in rat hepatocytes. Gastroenterology. 1995 Jul; 109(1):206-16. doi: 10.1016/0016-5085(95)90286-4. [PMID: 7540997]
  • S Ahmad, V Singh, G S Rao. Release of iron from ferritin by 1,2,4-benzenetriol. Chemico-biological interactions. 1995 May; 96(2):103-11. doi: 10.1016/0009-2797(94)03575-s. [PMID: 7537177]
  • V Singh, S Ahmad, G S Rao. Prooxidant and antioxidant properties of iron-hydroquinone and iron-1,2,4-benzenetriol complex. Implications for benzene toxicity. Toxicology. 1994 Mar; 89(1):25-33. doi: 10.1016/0300-483x(94)90130-9. [PMID: 7513907]
  • O Inoue, K Seiji, H Nakatsuka, T Watanabe, S Yin, G L Li, S X Cai, C Jin, M Ikeda. Excretion of 1,2,4-benzenetriol in the urine of workers exposed to benzene. British journal of industrial medicine. 1989 Aug; 46(8):559-65. doi: 10.1136/oem.46.8.559. [PMID: 2775675]
  • O Inoue, K Seiji, M Ikeda. Pathways for formation of catechol and 1,2,4-benzenetriol in rabbits. Bulletin of environmental contamination and toxicology. 1989 Aug; 43(2):220-4. doi: 10.1007/bf01701751. [PMID: 2775889]
  • E W Lee, J T Johnson, C D Garner. Inhibitory effect of benzene metabolites on nuclear DNA synthesis in bone marrow cells. Journal of toxicology and environmental health. 1989; 26(3):277-91. doi: 10.1080/15287398909531254. [PMID: 2926830]
  • G S Rao, S M Siddiqui, K P Pandya, R Shanker. Relative toxicity of metabolites of benzene in mice. Veterinary and human toxicology. 1988 Dec; 30(6):517-20. doi: NULL. [PMID: 3245112]
  • J W PORTEOUS, R T WILLIAMS. Studies in detoxication; the metabolism of benzene; the isolation of phenol, catechol, quinol and hydroxyquinol from ethereal sulphate fraction of the urine of rabbits receiving benzene orally. The Biochemical journal. 1949; 44(1):56-61. doi: NULL. [PMID: 18127452]