Echinatin (BioDeep_00000229863)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


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

化学式: C16H14O4 (270.0892044)
中文名称: 刺甘草查尔酮
谱图信息: 最多检出来源 Viridiplantae(plant) 1.21%

分子结构信息

SMILES: C1(O)=CC=C(C(=O)/C=C/C2C=CC(O)=CC=2OC)C=C1
InChI: InChI=1S/C16H14O4/c1-20-16-10-14(18)8-4-12(16)5-9-15(19)11-2-6-13(17)7-3-11/h2-10,17-18H,1H3/b9-5+

描述信息

Echinatin is a natural product found in Dracaena draco, Euphorbia helioscopia, and other organisms with data available.
Echinatin is a chalcone isolated from the Chinese herbal medicine Gancao with hepatoprotective and anti-inflammatory effects[1]. Echinatin can be quickly absorbed and eliminated and extensively distributed with an absolute bioavailability of approximately 6.81\\% in Rat[2].
Echinatin is a chalcone isolated from the Chinese herbal medicine Gancao with hepatoprotective and anti-inflammatory effects[1]. Echinatin can be quickly absorbed and eliminated and extensively distributed with an absolute bioavailability of approximately 6.81\% in Rat[2].

同义名列表

12 个代谢物同义名

Echinatin; 2-Propen-1-one, 3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-, (2E)-; (E)-3-(4-hydroxy-2-methoxy-phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one; (E)-3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one; (E)-3-(4-Hydroxy-2-methoxy-phenyl)-1-(4-hydroxy-phenyl)-propenone; 3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one; 4,4-DIHYDROXY-2-METHOXYCHALCONE; 4,4-dihydroxy-2-methoxychalcone; 4-Dihydroxy-2-methoxychalcone; Retrochalcone; Echinantin; (E) -3- (4-Hydroxy-2-methoxyphenyl) -1- (4-hydroxyphenyl) -2-propen-1-one



数据库引用编号

15 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

9 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(9)

  • echinatin biosynthesis: isoliquiritigenin ⟶ (2S)-liquiritigenin
  • echinatin biosynthesis: (2S)-liquiritigenin + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ 2-hydroxyliquiritigenin + H2O + an oxidized [NADPH-hemoprotein reductase]
  • echinatin biosynthesis: (2S)-liquiritigenin + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ 2-hydroxyliquiritigenin + H2O + an oxidized [NADPH-hemoprotein reductase]
  • echinatin biosynthesis: (2S)-liquiritigenin + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ 2-hydroxyliquiritigenin + H2O + an oxidized [NADPH-hemoprotein reductase]
  • echinatin biosynthesis: SAM + licodione ⟶ 2'-O-methyllicodione + H+ + SAH
  • echinatin biosynthesis: isoliquiritigenin ⟶ (2S)-liquiritigenin
  • echinatin biosynthesis: (2S)-liquiritigenin + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ 2-hydroxyliquiritigenin + H2O + an oxidized [NADPH-hemoprotein reductase]
  • echinatin biosynthesis: (2S)-liquiritigenin + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ 2-hydroxyliquiritigenin + H2O + an oxidized [NADPH-hemoprotein reductase]
  • echinatin biosynthesis: SAM + licodione ⟶ 2'-O-methyllicodione + H+ + SAH

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

43 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

  • Liang Sun, Duo Chen, Chenchen Zhao, Yujie Hu, Yuhao Xu, Shengnan Xia, Haiyan Yang, Xinyu Bao, Zhi Zhang, Chao Zhou, Qingxiu Zhang, Yun Xu. Echinatin protects from ischemic brain injury by attenuating NLRP3-related neuroinflammation. Neurochemistry international. 2024 May; 175(?):105676. doi: 10.1016/j.neuint.2024.105676. [PMID: 38336256]
  • Yanqiu You, Xudong Zhou, Qiuqin Tang, Tianshou Zhao, Juan Wang, Hanqin Huang, Jibing Chen, Zhongquan Qi, Fujun Li. Echinatin mitigates sevoflurane-induced neurotoxicity through regulation of ferroptosis and iron homeostasis. Aging. 2024 Mar; 16(5):4670-4683. doi: 10.18632/aging.205622. [PMID: 38446592]
  • Lei Ye, Ming Su, Xinyi Qiao, Shaowei Wang, Ke Zheng, Yang Zhu, Huitao Li, Yiyan Wang, Ren-Shan Ge. Chalcone derivatives from licorice inhibit human and rat gonadal 3β-hydroxysteroid dehydrogenases as therapeutic uses. Journal of ethnopharmacology. 2023 May; ?(?):116690. doi: 10.1016/j.jep.2023.116690. [PMID: 37245711]
  • Haiyu Xu, Shufen Li, Jiayuan Liu, Jinlong Cheng, Liping Kang, Weijie Li, Yute Zhong, Chaofa Wei, Lifeng Fu, Jianxun Qi, Yulan Zhang, Miaomiao You, Zhenxing Zhou, Chongtao Zhang, Haixia Su, Sheng Yao, Zhaoyin Zhou, Yulong Shi, Ran Deng, Qi Lv, Fengdi Li, Feifei Qi, Jie Chen, Siqin Zhang, Xiaojing Ma, Zhijian Xu, Shao Li, Yechun Xu, Ke Peng, Yi Shi, Hualiang Jiang, George F Gao, Luqi Huang. Bioactive compounds from Huashi Baidu decoction possess both antiviral and anti-inflammatory effects against COVID-19. Proceedings of the National Academy of Sciences of the United States of America. 2023 May; 120(18):e2301775120. doi: 10.1073/pnas.2301775120. [PMID: 37094153]
  • Huixin Tan, Fenghe Wang, Jiahuan Hu, Xiaoyan Duan, Wanting Bai, Xinbo Wang, Baolian Wang, Yan Su, Jinping Hu. Inhibitory interaction of flavonoids with organic cation transporter 2 and their structure-activity relationships for predicting nephroprotective effects. Journal of applied toxicology : JAT. 2023 Apr; ?(?):. doi: 10.1002/jat.4474. [PMID: 37057715]
  • Wen-Qing Mu, Guang Xu, Jia Zhao, Yuan-Yuan Chen, Zhao-Fang Bai, Xiao-He Xiao. [Preventive and therapeutic effect of bioactive component of licorice on antidepressant-induced liver injury]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Nov; 47(22):6146-6154. doi: 10.19540/j.cnki.cjcmm.20220608.402. [PMID: 36471939]
  • Guang Xu, Shubin Fu, Xiaoyan Zhan, Zhilei Wang, Ping Zhang, Wei Shi, Nan Qin, Yuanyuan Chen, Chunyu Wang, Ming Niu, Yuming Guo, Jiabo Wang, Zhaofang Bai, Xiaohe Xiao. Echinatin effectively protects against NLRP3 inflammasome-driven diseases by targeting HSP90. JCI insight. 2021 01; 6(2):. doi: 10.1172/jci.insight.134601. [PMID: 33350984]
  • Yunjia Hu, Meiqin Liu, Hongbo Qin, Haofeng Lin, Xiaoping An, Zhengli Shi, Lihua Song, Xinglou Yang, Huahao Fan, Yigang Tong. Artemether, Artesunate, Arteannuin B, Echinatin, Licochalcone B and Andrographolide Effectively Inhibit SARS-CoV-2 and Related Viruses In Vitro. Frontiers in cellular and infection microbiology. 2021; 11(?):680127. doi: 10.3389/fcimb.2021.680127. [PMID: 34527599]
  • Jing-Ran Fan, Yi Kuang, Ze-Yuan Dong, Yang Yi, Yan-Xia Zhou, Bin Li, Xue Qiao, Min Ye. Prenylated Phenolic Compounds from the Aerial Parts of Glycyrrhiza uralensis as PTP1B and α-Glucosidase Inhibitors. Journal of natural products. 2020 04; 83(4):814-824. doi: 10.1021/acs.jnatprod.9b00262. [PMID: 32196343]
  • Ha-Na Oh, Mee-Hyun Lee, Eunae Kim, Ah-Won Kwak, Ji-Hye Seo, Goo Yoon, Seung-Sik Cho, Joon-Seok Choi, Sang-Myeong Lee, Kang-Seok Seo, Jung-Il Chae, Jung-Hyun Shim. Dual inhibition of EGFR and MET by Echinatin retards cell growth and induces apoptosis of lung cancer cells sensitive or resistant to gefitinib. Phytotherapy research : PTR. 2020 Feb; 34(2):388-400. doi: 10.1002/ptr.6530. [PMID: 31698509]
  • Tianran Li, Weijian Ye, Binge Huang, Xiaojie Lu, Xixi Chen, Yijing Lin, Congcong Wen, Xianqin Wang. Determination and pharmacokinetic study of echinatin by UPLC-MS/MS in rat plasma. Journal of pharmaceutical and biomedical analysis. 2019 May; 168(?):133-137. doi: 10.1016/j.jpba.2019.02.023. [PMID: 30807917]
  • Yi Kuang, Bin Li, Jingran Fan, Xue Qiao, Min Ye. Antitussive and expectorant activities of licorice and its major compounds. Bioorganic & medicinal chemistry. 2018 01; 26(1):278-284. doi: 10.1016/j.bmc.2017.11.046. [PMID: 29224994]
  • Yan Lin, Yi Kuang, Kai Li, Shuang Wang, Shuai Ji, Kuan Chen, Wei Song, Xue Qiao, Min Ye. Nrf2 activators from Glycyrrhiza inflata and their hepatoprotective activities against CCl4-induced liver injury in mice. Bioorganic & medicinal chemistry. 2017 10; 25(20):5522-5530. doi: 10.1016/j.bmc.2017.08.018. [PMID: 28835349]
  • Yan Lin, Yi Kuang, Kai Li, Shuang Wang, Wei Song, Xue Qiao, Gulnar Sabir, Min Ye. Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata. Bioorganic & medicinal chemistry. 2017 07; 25(14):3706-3713. doi: 10.1016/j.bmc.2017.05.009. [PMID: 28522265]
  • Xing-Han Tian, Chao-Liang Liu, Hai-Li Jiang, Yan Zhang, Ji-Chun Han, Ju Liu, Meng Chen. Cardioprotection provided by Echinatin against ischemia/reperfusion in isolated rat hearts. BMC cardiovascular disorders. 2016 05; 16(?):119. doi: 10.1186/s12872-016-0294-3. [PMID: 27246834]
  • Shuai Ji, Ziwei Li, Wei Song, Yongrui Wang, Wenfei Liang, Kai Li, Shunan Tang, Qi Wang, Xue Qiao, Demin Zhou, Siwang Yu, Min Ye. Bioactive Constituents of Glycyrrhiza uralensis (Licorice): Discovery of the Effective Components of a Traditional Herbal Medicine. Journal of natural products. 2016 Feb; 79(2):281-92. doi: 10.1021/acs.jnatprod.5b00877. [PMID: 26841168]
  • Minpei Kuroda, Yoshihiro Mimaki, Shinichi Honda, Hozumi Tanaka, Shinichi Yokota, Tatsumasa Mae. Phenolics from Glycyrrhiza glabra roots and their PPAR-gamma ligand-binding activity. Bioorganic & medicinal chemistry. 2010 Jan; 18(2):962-70. doi: 10.1016/j.bmc.2009.11.027. [PMID: 20022509]
  • Goo Yoon, Woojung Lee, Su-Nam Kim, Seung Hoon Cheon. Inhibitory effect of chalcones and their derivatives from Glycyrrhiza inflata on protein tyrosine phosphatase 1B. Bioorganic & medicinal chemistry letters. 2009 Sep; 19(17):5155-7. doi: 10.1016/j.bmcl.2009.07.054. [PMID: 19632832]