3,4,5-Trimethoxycinnamic acid (BioDeep_00000017702)

Main id: BioDeep_00000397998

 

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


3,4,5-Trimethoxycinnamic acid, analytical reference material

化学式: C12H14O5 (238.0841194)
中文名称: 3,4,5-三甲氧基肉桂酸, (E)-3,4,5-三甲氧基肉桂酸
谱图信息: 最多检出来源 () 0%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

3,4,5-Trimethoxycinnamic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/3,4,5-trimethoxycinnamic_acid (retrieved 2024-11-09) (BioDeep RN: BioDeep_00000017702). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: COC1=C(OC)C(OC)=CC(/C=C/C(O)=O)=C1
InChI: InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)

描述信息

3, 4, 5-trimethoxycinnamic acid is a methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions. It has a role as an allergen. It is a conjugate acid of a 3,4,5-trimethoxycinnamate. 3, 4, 5-Trimethoxycinnamic acid is an organic acid found in normal human urine (PMID:6992730, 6511847). Trimethoxycinnamate is a natural aromatic ester from Piper longum that inhibits expression of cell adhesion molecules on endothelial cells (TNF- -induced expression of intercellular adhesion molecule-1 (ICAM-1) and E-Selectin and vascular adhesion molecules-1 (VCAM-1)), without being toxic to endothelial cells. (PMID:16313198).
3,4,5-trimethoxycinnamic acid is a methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions. It has a role as an allergen. It is a conjugate acid of a 3,4,5-trimethoxycinnamate.
3,4,5-Trimethoxycinnamic acid is a natural product found in Piper tuberculatum, Polygala tenuifolia, and Piper swartzianum with data available.
3,4,5-Trimethoxycinnamic acid is an organic acid found in normal human urine. (PMID: 6992730, 6511847)
(E)-3,4,5-Trimethoxycinnamic acid (TMCA) is a cinnamic acid substituted by multi-methoxy groups. (E)-3,4,5-Trimethoxycinnamic acid is an orally active and potent GABAA/BZ receptor agonist. (E)-3,4,5-Trimethoxycinnamic exhibits favourable binding affinity to 5-HT2C and 5-HT1A receptor, with IC50 values of 2.5 and 7.6 μM, respectively. (E)-3,4,5-Trimethoxycinnamic acid shows anticonvulsant and sedative activity. (E)-3,4,5-Trimethoxycinnamic acid can be used for the research of insomnia, headache and epilepsy[1][2][3].
(E)-3,4,5-Trimethoxycinnamic acid (TMCA) is a cinnamic acid substituted by multi-methoxy groups. (E)-3,4,5-Trimethoxycinnamic acid is an orally active and potent GABAA/BZ receptor agonist. (E)-3,4,5-Trimethoxycinnamic exhibits favourable binding affinity to 5-HT2C and 5-HT1A receptor, with IC50 values of 2.5 and 7.6 μM, respectively. (E)-3,4,5-Trimethoxycinnamic acid shows anticonvulsant and sedative activity. (E)-3,4,5-Trimethoxycinnamic acid can be used for the research of insomnia, headache and epilepsy[1][2][3].
3,4,5-Trimethoxycinnamic acid is a phenylpropanoid isolated from the roots of Polygala tenuifolia WILLD, with anti-stress effect, prolonging the sleeping time in animals[1][2]. 3,4,5-Trimethoxycinnamic acid increases expression of GAD65 and γ-subunit of GABAA receptor, but shows no effect on the amounts of α-, β-subunits[2].
3,4,5-Trimethoxycinnamic acid is a phenylpropanoid isolated from the roots of Polygala tenuifolia WILLD, with anti-stress effect, prolonging the sleeping time in animals[1][2]. 3,4,5-Trimethoxycinnamic acid increases expression of GAD65 and γ-subunit of GABAA receptor, but shows no effect on the amounts of α-, β-subunits[2].
3,4,5-Trimethoxycinnamic acid is a phenylpropanoid isolated from the roots of Polygala tenuifolia WILLD, with anti-stress effect, prolonging the sleeping time in animals[1][2]. 3,4,5-Trimethoxycinnamic acid increases expression of GAD65 and γ-subunit of GABAA receptor, but shows no effect on the amounts of α-, β-subunits[2].

同义名列表

42 个代谢物同义名

3,4,5-Trimethoxycinnamic acid, analytical reference material; 2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, (2E)-; 2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-, (E)-; 3,4,5-Trimethoxycinnamic acid, predominantly trans; (2E)-3-(3,4,5-Trimethoxyphenyl)-2-propenoic acid; (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid; (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid; 2-Propenoic acid, 3-(3,4,5-trimethoxyphenyl)-; (2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoate; 2-10-00-00354 (Beilstein Handbook Reference); (E)-3-(3,4,5-trimethoxyphenyl) acrylic acid; 3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid; 3-(3,4,5-trimethoxyphenyl)-2-propenoic acid; (2E)-3-(3,4,5-trimethoxyphenyl)acrylic acid; (E)-3-(3,4,5-trimethoxyphenyl)acrylic acid; 3,4,5-Trimethoxycinnamic acid, pred. trans; 3-(3,5-Trimethoxyphenyl)-2-propenoic acid; (E)-3-(3,4,5-trimethoxyphenyl)acrylicacid; 3-(3,4,5-Trimethoxyphenyl)propenoic acid; 2-Propenoic acid,4,5-trimethoxyphenyl)-; 3-(3,4,5-trimethoxyphenyl)acrylic acid; Cinnamic acid, 3,4,5-trimethoxy-, (E)-; 3,4,5-Trimethoxy-trans-cinnamic acid; 3,4,5-Trimethoxycinnamic acid (TMCA); trans-3,4,5-Trimethoxycinnamic acid; 3,4,5-Trimethoxycinnamic acid, 97\\%; 3,4,5-Trimethoxyphenylacrylic acid; (e)-3,4,5-trimethoxycinnamic acid; Cinnamic acid, 3,4,5-trimethoxy-; 3, 4, 5-Trimethoxycinnamic Acid; 3,4,5-Trimethoxy cinnamic acid; 3,4,5-Trimethoxyphenylacrylate; 3,4,5-Trimethoxycinnamic acid; Cinnamic acid,4,5-trimethoxy-; 3,5-Trimethoxycinnamic acid; 3,4,5-Trimethoxy cinnamate; 3,4,5-Trimethoxycinnamate; SINAPIC ACID METHYL ETHER; O-Methylsinapic acid; O-Methylsinapate; Spectrum5_000448; TMCA



数据库引用编号

16 个数据库交叉引用编号

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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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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

  • Xin Zhao, Baoxin Xu, Peng Wu, Pan Zhao, Changchuan Guo, Yueli Cui, Yanxue Zhang, Xuelan Zhang, Huifen Li. UHPLC-MS/MS method for pharmacokinetic and bioavailability determination of five bioactive components in raw and various processed products of Polygala tenuifolia in rat plasma. Pharmaceutical biology. 2020 Dec; 58(1):969-978. doi: 10.1080/13880209.2020.1818790. [PMID: 32956609]
  • Yajun Bai, Xirui He, Yujun Bai, Ying Sun, Zefeng Zhao, Xufei Chen, Bin Li, Jing Xie, Yang Li, Pu Jia, Xue Meng, Ye Zhao, Yanrui Ding, Chaoni Xiao, Shixiang Wang, Jie Yu, Sha Liao, Yajun Zhang, Zhiling Zhu, Qiang Zhang, Yuhui Zhao, Fanggang Qin, Yi Zhang, Xiaoyang Wei, Min Zeng, Jing Liang, Ye Cuan, Guangzhi Shan, Tai-Ping Fan, Biao Wu, Xiaohui Zheng. Polygala tenuifolia-Acori tatarinowii herbal pair as an inspiration for substituted cinnamic α-asaronol esters: Design, synthesis, anticonvulsant activity, and inhibition of lactate dehydrogenase study. European journal of medicinal chemistry. 2019 Dec; 183(?):111650. doi: 10.1016/j.ejmech.2019.111650. [PMID: 31539780]
  • Muhammad T Islam, Abul B R Khalipha, Rajat Bagchi, Milon Mondal, Shanita Z Smrity, Shaikh J Uddin, Jamil A Shilpi, Razina Rouf. Anticancer activity of thymol: A literature-based review and docking study with Emphasis on its anticancer mechanisms. IUBMB life. 2019 01; 71(1):9-19. doi: 10.1002/iub.1935. [PMID: 30308112]
  • Baoxin Xu, Congcong Qu, Wenhua Zheng, Yaya Xi, Xin Zhao, Huifen Li, Jiangting Liu, Xuelan Zhang. UHPLC-MS/MS method for simultaneous determination of Radix Polygalae glycolipids and organic acids in rat plasma and application in a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Nov; 1100-1101(?):165-173. doi: 10.1016/j.jchromb.2018.09.037. [PMID: 30340065]
  • Chang-Yuan Chen, Xu-Dong Wei, Chang-Rui Chen. 3,4,5-Trimethoxycinnamic acid, one of the constituents of Polygalae Radix exerts anti-seizure effects by modulating GABAAergic systems in mice. Journal of pharmacological sciences. 2016 May; 131(1):1-5. doi: 10.1016/j.jphs.2015.07.021. [PMID: 26260747]
  • Qian Wang, Bing-Xin Xiao, Rui-Le Pan, Xin-Min Liu, Yong-Hong Liao, Li Feng, Fang-Rui Cao, Qi Chang. An LC-MS/MS method for simultaneous determination of three Polygala saponin hydrolysates in rat plasma and its application to a pharmacokinetic study. Journal of ethnopharmacology. 2015 Jul; 169(?):401-6. doi: 10.1016/j.jep.2015.04.033. [PMID: 25922266]
  • Xiao-Bo Yu, Guang-Lu Liu, Bin Zhu, Kai Hao, Fei Ling, Gao-Xue Wang. In vitro immunocompetence of two compounds isolated from Polygala tenuifolia and development of resistance against grass carp reovirus (GCRV) and Dactylogyrus intermedius in respective host. Fish & shellfish immunology. 2014 Dec; 41(2):541-8. doi: 10.1016/j.fsi.2014.10.004. [PMID: 25450998]
  • Zhenghang Zhao, Minfeng Fang, Dandan Xiao, Mei Liu, Nadezhda Fefelova, Chen Huang, Wei-Jin Zang, Lai-Hua Xie. Potential antiarrhythmic effect of methyl 3,4,5-trimethoxycinnamate, a bioactive substance from roots of polygalae radix: suppression of triggered activities in rabbit myocytes. Biological & pharmaceutical bulletin. 2013; 36(2):238-44. doi: 10.1248/bpb.b12-00654. [PMID: 23196428]
  • Namki Cho, Jungmoo Huh, Heejung Yang, Eun Ju Jeong, Young Choong Kim, Jinwoong Kim, Sang Hyun Sung. Chemical constituents of Polygala tenuifolia roots and their inhibitory activity on lipopolysaccharide-induced nitric oxide production in BV2 microglia. Journal of enzyme inhibition and medicinal chemistry. 2012 Feb; 27(1):1-4. doi: 10.3109/14756366.2011.562203. [PMID: 21740104]
  • Heidi Rose Bokesch, Roberta Scott Gardella, Daniel Christopher Rabe, Donald Paul Bottaro, William Marston Linehan, James Brislin McMahon, Tawnya Carlene McKee. A new hypoxia inducible factor-2 inhibitory pyrrolinone alkaloid from roots and stems of Piper sarmentosum. Chemical & pharmaceutical bulletin. 2011; 59(9):1178-9. doi: 10.1248/cpb.59.1178. [PMID: 21881266]
  • Fang-Pey Chen, Maw-Shiou Jong, Yu-Chun Chen, Yen-Ying Kung, Tzeng-Ji Chen, Fun-Jou Chen, Shinn-Jang Hwang. Prescriptions of Chinese Herbal Medicines for Insomnia in Taiwan during 2002. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):236341. doi: 10.1093/ecam/nep018. [PMID: 19339485]
  • Carolina Arevalo, Cinzia Lotti, Anna Lisa Piccinelli, Mariateresa Russo, Ines Ruiz, Luca Rastrelli. Magnoflorine and phenolic derivatives from the leaves of Croton xalapensis L. (Euphorbiaceae). Natural product communications. 2009 Dec; 4(12):1697-700. doi: ". [PMID: 20120110]
  • Claude Bomal, Frank Bedon, Sébastien Caron, Shawn D Mansfield, Caroline Levasseur, Janice E K Cooke, Sylvie Blais, Laurence Tremblay, Marie-Josée Morency, Nathalie Pavy, Jacqueline Grima-Pettenati, Armand Séguin, John Mackay. Involvement of Pinus taeda MYB1 and MYB8 in phenylpropanoid metabolism and secondary cell wall biogenesis: a comparative in planta analysis. Journal of experimental botany. 2008; 59(14):3925-39. doi: 10.1093/jxb/ern234. [PMID: 18805909]
  • Keiko Kawashima, Daishi Miyako, Yasuyuki Ishino, Toshiaki Makino, Ken-Ichi Saito, Yoshihiro Kano. Anti-stress effects of 3,4,5-trimethoxycinnamic acid, an active constituent of roots of Polygala tenuifolia (Onji). Biological & pharmaceutical bulletin. 2004 Aug; 27(8):1317-9. doi: 10.1248/bpb.27.1317. [PMID: 15305046]
  • R Viswanathan, S Subramanian, T G Radha. Effect of hypoxia on regional lung perfusion, by scanning. Respiration; international review of thoracic diseases. 1979; 37(3):142-7. doi: 10.1159/000194023. [PMID: 441541]
  • P Szylman, O S Better, C Chaimowitz, A Rosler. Role of hyperkalemia in the metabolic acidosis of isolated hypoaldosteronism. The New England journal of medicine. 1976 Feb; 294(7):361-5. doi: 10.1056/nejm197602122940703. [PMID: 1674]