2'-Hydroxy-4,4',6'-trimethoxychalcone (BioDeep_00000017323)

 

Secondary id: BioDeep_00000270223

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-, (2E)-

化学式: C18H18O5 (314.1154)
中文名称: 2-羟基-4,4,6-三甲氧基查耳酮, 黄卡瓦胡椒素 A, 黄卡瓦胡椒素A, 卡瓦胡椒素A, 2'-羟基-4,4',6'-三甲氧基查耳酮
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 56.84%

分子结构信息

SMILES: c1(cc(c(c(c1)OC)C(=O)/C=C/c1ccc(cc1)OC)O)OC
InChI: InChI=1S/C18H18O5/c1-21-13-7-4-12(5-8-13)6-9-15(19)18-16(20)10-14(22-2)11-17(18)23-3/h4-11,20H,1-3H3/b9-6+

描述信息

Flavokawain A is a member of chalcones.
2-Hydroxy-4,4,6-trimethoxychalcone is a natural product found in Dahlia tenuicaulis, Piper methysticum, and other organisms with data available.
See also: Piper methysticum root (part of).
2-Hydroxy-4,4,6-trimethoxychalcone is found in beverages. 2-Hydroxy-4,4,6-trimethoxychalcone is found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002).
Found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
(E)-Flavokawain A, a chalcone extracted from Kava, has anticarcinogenic effect. (E)-Flavokawain A induces apoptosis in bladder cancer cells by involvement of bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice[1].
(E)-Flavokawain A, a chalcone extracted from Kava, has anticarcinogenic effect. (E)-Flavokawain A induces apoptosis in bladder cancer cells by involvement of bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice[1].
Flavokawain A, a proming anticarcinogenic agent, is a chalcone from kava extract with anti-tumor activity. Flavokawain A induces cell apoptosis by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway. Flavokawain A has the potential for the study of bladder cancer[1].
Flavokawain A, a proming anticarcinogenic agent, is a chalcone from kava extract with anti-tumor activity. Flavokawain A induces cell apoptosis by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway. Flavokawain A has the potential for the study of bladder cancer[1].

同义名列表

22 个代谢物同义名

2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-, (2E)-; 2-Propen-1-one,1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-, (2E)-; (E)-1-(2-hydroxy-4,6-dimethoxy-phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one; (2E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one; (2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one; (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one; 2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-; 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one; 2-Hydroxy-4,4,6-trimethoxychalcone, 98\\%; 2-Hydroxy-4,4,6-trimethoxychalcone; CGIBCVBDFUTMPT-RMKNXTFCSA-N; 4-Methoxyflavokawain B; (E)-Flavokawain A; FLAVOKAVAIN A(P); UNII-8OM2XZ2ZM3; Flavokavain A; Flavokawain A; flavokavin A; Flavokawin A; Flavokawain; 8OM2XZ2ZM3; MCULE-8624027603



数据库引用编号

22 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

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)

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

  • Shuangjie Liu, Zhuonan Liu, Chiyuan Piao, Zhe Zhang, Chuize Kong, Lei Yin, Xi Liu. Flavokawain A is a natural inhibitor of PRMT5 in bladder cancer. Journal of experimental & clinical cancer research : CR. 2022 Oct; 41(1):293. doi: 10.1186/s13046-022-02500-4. [PMID: 36199122]
  • Xiaojun Zhao, Chao Su, Ruru Ren, Bo Zhang, Yingli Wang, Xiaojuan Su, Fangfang Lu, Rong Zong, Lingling Yang, Wannian Zhang, Xueqin Ma. Simultaneous determination of both kavalactone and flavokawain constituents by different single-marker methods in kava. Journal of separation science. 2021 Jul; 44(14):2705-2716. doi: 10.1002/jssc.202100198. [PMID: 33951745]
  • Antonio Celentano, Callisthenis Yiannis, Rita Paolini, Pangzhen Zhang, Camile S Farah, Nicola Cirillo, Tami Yap, Michael McCullough. Kava constituents exert selective anticancer effects in oral squamous cell carcinoma cells in vitro. Scientific reports. 2020 09; 10(1):15904. doi: 10.1038/s41598-020-73058-4. [PMID: 32985597]
  • Hsin-Ling Yang, Ting-Yu Yang, Yugandhar Vudhya Gowrisankar, Chun-Huei Liao, Jiunn-Wang Liao, Pei-Jane Huang, You-Cheng Hseu. Suppression of LPS-Induced Inflammation by Chalcone Flavokawain A through Activation of Nrf2/ARE-Mediated Antioxidant Genes and Inhibition of ROS/NFκB Signaling Pathways in Primary Splenocytes. Oxidative medicine and cellular longevity. 2020; 2020(?):3476212. doi: 10.1155/2020/3476212. [PMID: 32617135]
  • Keanu D Pinner, Christina T K Wales, Rachel A Gristock, Hoa T Vo, Nadine So, Aaron T Jacobs. Flavokawains A and B from kava (Piper methysticum) activate heat shock and antioxidant responses and protect against hydrogen peroxide-induced cell death in HepG2 hepatocytes. Pharmaceutical biology. 2016 Sep; 54(9):1503-12. doi: 10.3109/13880209.2015.1107104. [PMID: 26789234]
  • Xuesen Li, Noriko N Yokoyama, Saiyang Zhang, Lina Ding, Hong-min Liu, Michael B Lilly, Dan Mercola, Xiaolin Zi. Flavokawain A induces deNEDDylation and Skp2 degradation leading to inhibition of tumorigenesis and cancer progression in the TRAMP transgenic mouse model. Oncotarget. 2015 Dec; 6(39):41809-24. doi: 10.18632/oncotarget.6166. [PMID: 26497688]
  • Nadiah Abu, Nurul Elyani Mohameda, Nirosha Tangarajoo, Swee Keong Yeap, M Nadeem Akhtar, Mohd Puad Abdullah, Abdul Rahman Omar, Noorjahan Banu Alitheen. In vitro Toxicity and in vivo Immunomodulatory Effects of Flavokawain A and Flavokawain B in Balb/C Mice. Natural product communications. 2015 Jul; 10(7):1199-202. doi: . [PMID: 26411010]
  • Nadiah Abu, Nurul Elyani Mohamed, Swee Keong Yeap, Kian Lam Lim, M Nadeem Akhtar, Aimi Jamil Zulfadli, Beh Boon Kee, Mohd Puad Abdullah, Abdul Rahman Omar, Noorjahan Banu Alitheen. In Vivo Anti-Tumor Effects of Flavokawain A in 4T1 Breast Cancer Cell-Challenged Mice. Anti-cancer agents in medicinal chemistry. 2015; 15(7):905-15. doi: 10.2174/187152061507150713111557. [PMID: 26179368]
  • V Lebot, T K T Do, L Legendre. Detection of flavokavins (A, B, C) in cultivars of kava (Piper methysticum) using high performance thin layer chromatography (HPTLC). Food chemistry. 2014 May; 151(?):554-60. doi: 10.1016/j.foodchem.2013.11.120. [PMID: 24423570]
  • Nadiah Abu, M Nadeem Akhtar, Swee Keong Yeap, Kian Lam Lim, Wan Yong Ho, Aimi Jamil Zulfadli, Abdul Rahman Omar, Mohd Roslan Sulaiman, Mohd Puad Abdullah, Noorjahan Banu Alitheen. Flavokawain A induces apoptosis in MCF-7 and MDA-MB231 and inhibits the metastatic process in vitro. PloS one. 2014; 9(10):e105244. doi: 10.1371/journal.pone.0105244. [PMID: 25286005]
  • Zhongbo Liu, Xia Xu, Xuesen Li, Shuman Liu, Anne R Simoneau, Feng He, Xue-Ru Wu, Xiaolin Zi. Kava chalcone, flavokawain A, inhibits urothelial tumorigenesis in the UPII-SV40T transgenic mouse model. Cancer prevention research (Philadelphia, Pa.). 2013 Dec; 6(12):1365-75. doi: 10.1158/1940-6207.capr-13-0219. [PMID: 24121102]
  • Sook Wah Tang, Mohd Aspollah Sukari, Mawardi Rahmani, Nordin Hj Lajis, Abdul Manaf Ali. A new abietene diterpene and other constituents from Kaempferia angustifolia Rosc. Molecules (Basel, Switzerland). 2011 Apr; 16(4):3018-28. doi: 10.3390/molecules16043018. [PMID: 21475124]
  • Anastasia Detsi, Maya Majdalani, Christos A Kontogiorgis, Dimitra Hadjipavlou-Litina, Panagiotis Kefalas. Natural and synthetic 2'-hydroxy-chalcones and aurones: synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity. Bioorganic & medicinal chemistry. 2009 Dec; 17(23):8073-85. doi: 10.1016/j.bmc.2009.10.002. [PMID: 19853459]
  • José C Aponte, Manuela Verástegui, Edith Málaga, Mirko Zimic, Miguel Quiliano, Abraham J Vaisberg, Robert H Gilman, Gerald B Hammond. Synthesis, cytotoxicity, and anti-Trypanosoma cruzi activity of new chalcones. Journal of medicinal chemistry. 2008 Oct; 51(19):6230-4. doi: 10.1021/jm800812k. [PMID: 18798609]
  • Mauricio Cabrera, Macarena Simoens, Gabriela Falchi, M Laura Lavaggi, Oscar E Piro, Eduardo E Castellano, Anabel Vidal, Amaia Azqueta, Antonio Monge, Adela López de Ceráin, Gabriel Sagrera, Gustavo Seoane, Hugo Cerecetto, Mercedes González. Synthetic chalcones, flavanones, and flavones as antitumoral agents: biological evaluation and structure-activity relationships. Bioorganic & medicinal chemistry. 2007 May; 15(10):3356-67. doi: 10.1016/j.bmc.2007.03.031. [PMID: 17383189]
  • Xiaolin Zi, Anne R Simoneau. Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice. Cancer research. 2005 Apr; 65(8):3479-86. doi: 10.1158/0008-5472.can-04-3803. [PMID: 15833884]
  • M Morimoto, S Kumeda, K Komai. Insect antifeedant flavonoids from Gnaphalium affine D. Don. Journal of agricultural and food chemistry. 2000 May; 48(5):1888-91. doi: 10.1021/jf990282q. [PMID: 10820110]