Biliatresone (BioDeep_00000395531)

   

PANOMIX_OTCML-2023 Toxin


代谢物信息卡片


2-[2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl]-1,3-dimethoxy-4,5-methylenedioxybenzene

化学式: C18H16O6 (328.0947)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=C(C(=C2C(=C1)OCO2)OC)C(=O)C(=C)C3=CC=CC=C3O
InChI: InChI=1S/C18H16O6/c1-10(11-6-4-5-7-12(11)19)16(20)15-13(21-2)8-14-17(18(15)22-3)24-9-23-14/h4-8,19H,1,9H2,2-3H3

描述信息

Biliatresone is a member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted at positions 5 by a 2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl group and at positions 4 and 6 by methoxy groups. A very rare type of isoflavonoid-related 1,2-diaryl-2-propenone found in Dysphania glomulifera (red crumbweed) and D. littoralis, the enone moiety is particularly reactive, undergoing ready Michael addition of water and methanol. Biliatresone has been found to cause extrahepatic biliary atresia (obliteration or discontinuity of the extrahepatic biliary system, resulting in obstruction to bile flow) in a zebrafish model. It has a role as a toxin and a plant metabolite. It is a member of benzodioxoles, an enone, an aromatic ketone, an aromatic ether and a member of phenols.
A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted at positions 5 by a 2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl group and at positions 4 and 6 by methoxy groups. A very rare type of isoflavonoid-related 1,2-diaryl-2-propenone found in Dysphania glomulifera (red crumbweed) and D. littoralis, the enone moiety is particularly reactive, undergoing ready Michael addition of water and methanol. Biliatresone has been found to cause extrahepatic biliary atresia (obliteration or discontinuity of the extrahepatic biliary system, resulting in obstruction to bile flow) in a zebrafish model.

同义名列表

5 个代谢物同义名

2-[2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl]-1,3-dimethoxy-4,5-methylenedioxybenzene; 1-(4,6-Dimethoxy-2H-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one; 1-(4,6-Dimethoxybenzo[d][1,3]dioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one; 1-(4,6-dimethoxy-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one; Biliatresone



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

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INOH(0)

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0 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。

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亚细胞结构定位 关联基因列表


文献列表

  • Yue Hai-Bing, Menon Sudheer Sivasankaran, Babu Rosana Ottakandathil, Wu Zhong-Luan, So Man-Ting, Chung Patrick Ho-Yu, Wong Kenneth Kak-Yuen, Tam Paul Kwong-Hang, Lui Vincent Chi-Hang. Environmental Toxin Biliatresone-Induced Biliary Atresia-like Abnormal Cilia and Bile Duct Cell Development of Human Liver Organoids. Toxins. 2024 Mar; 16(3):. doi: 10.3390/toxins16030144. [PMID: 38535810]
  • Kapish Gupta, Jimmy P Xu, Tamir Diamond, Iris E M de Jong, Andrew Glass, Jessica Llewellyn, Neil D Theise, Orith Waisbourd-Zinman, Jeffrey D Winkler, Edward M Behrens, Clementina Mesaros, Rebecca G Wells. Low-dose biliatresone treatment of pregnant mice causes subclinical biliary disease in their offspring: Evidence for a spectrum of neonatal injury. PloS one. 2024; 19(4):e0301824. doi: 10.1371/journal.pone.0301824. [PMID: 38578745]
  • Hans Christian Schmidt, Johanna Hagens, Pauline Schuppert, Birgit Appl, Laia Pagerols Raluy, Magdalena Trochimiuk, Clara Philippi, Zhongwen Li, Konrad Reinshagen, Christian Tomuschat. Biliatresone induces cholangiopathy in C57BL/6J neonates. Scientific reports. 2023 06; 13(1):10574. doi: 10.1038/s41598-023-37354-z. [PMID: 37386088]
  • Xiao Zhao, Kristin Lorent, Diana Escobar-Zarate, Ramakrishnan Rajagopalan, Kathleen M Loomes, Kevin Gillespie, Clementina Mesaros, Michelle A Estrada, Ian A Blair, Jeffrey D Winkler, Nancy B Spinner, Marcella Devoto, Michael Pack. Impaired Redox and Protein Homeostasis as Risk Factors and Therapeutic Targets in Toxin-Induced Biliary Atresia. Gastroenterology. 2020 09; 159(3):1068-1084.e2. doi: 10.1053/j.gastro.2020.05.080. [PMID: 32505743]
  • Sophia Fried, Dafna Gilboa, Adi Har-Zahav, Pierre-Marie Lavrut, Yu Du, Sara Karjoo, Pierre Russo, Raanan Shamir, Rebecca G Wells, Orith Waisbourd-Zinman. Extrahepatic cholangiocyte obstruction is mediated by decreased glutathione, Wnt and Notch signaling pathways in a toxic model of biliary atresia. Scientific reports. 2020 05; 10(1):7599. doi: 10.1038/s41598-020-64503-5. [PMID: 32371929]
  • Mark Davenport. Biliary atresia: From Australia to the zebrafish. Journal of pediatric surgery. 2016 Feb; 51(2):200-5. doi: 10.1016/j.jpedsurg.2015.10.058. [PMID: 26653951]
  • Kyung A Koo, Kristin Lorent, Weilong Gong, Peter Windsor, Stephen J Whittaker, Michael Pack, Rebecca G Wells, John R Porter. Biliatresone, a Reactive Natural Toxin from Dysphania glomulifera and D. littoralis: Discovery of the Toxic Moiety 1,2-Diaryl-2-Propenone. Chemical research in toxicology. 2015 Aug; 28(8):1519-21. doi: 10.1021/acs.chemrestox.5b00227. [PMID: 26175131]