Ethyl_protocatechuate (BioDeep_00000230957)

 

Secondary id: BioDeep_00000178867, BioDeep_00000266549, BioDeep_00000271602, BioDeep_00000863353

PANOMIX_OTCML-2023


代谢物信息卡片


InChI=1/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H

化学式: C9H10O4 (182.057906)
中文名称: 3,4-二羟基苯甲酸乙酯, 原儿茶酸乙酯, 3,4-二羟基苯甲酸乙酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 78.26%

分子结构信息

SMILES: CCOC(=O)C1=CC(=C(C=C1)O)O
InChI: InChI=1S/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H3

描述信息

Ethyl 3,4-dihydroxybenzoate is an ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa. It has a role as an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor, an antibacterial agent, an antioxidant, an apoptosis inducer and a plant metabolite. It is an ethyl ester and a member of catechols. It is functionally related to a 3,4-dihydroxybenzoic acid.
Ethyl 3,4-dihydroxybenzoate is a natural product found in Liatris elegans, Xylocarpus granatum, and other organisms with data available.
An ethyl ester resulting from the formal condensation of the carboxy group of 3,4-dihydroxybenzoic acid with ethanol. It is the anti-oxidative component of peanut seed testa.
Ethyl 3,4-dihydroxybenzoate (Ethyl protocatechuate), an antioxidant, is a prolyl-hydroxylase inhibitor found in the testa of peanut seeds. Ethyl 3,4-dihydroxybenzoate protects myocardium by activating NO synthase and generating mitochondrial ROS. Ethyl 3,4-dihydroxybenzoate induces cell autophagy and apoptosis in ESCC cells. Ethyl 3,4-dihydroxybenzoate is a collagen synthesis inhibitor and has a bone protecting-effect[1][2][3][4].
Ethyl 3,4-dihydroxybenzoate (Ethyl protocatechuate), an antioxidant, is a prolyl-hydroxylase inhibitor found in the testa of peanut seeds. Ethyl 3,4-dihydroxybenzoate protects myocardium by activating NO synthase and generating mitochondrial ROS. Ethyl 3,4-dihydroxybenzoate induces cell autophagy and apoptosis in ESCC cells. Ethyl 3,4-dihydroxybenzoate is a collagen synthesis inhibitor and has a bone protecting-effect[1][2][3][4].
Ethyl 3,4-dihydroxybenzoate (Ethyl protocatechuate), an antioxidant, is a prolyl-hydroxylase inhibitor found in the testa of peanut seeds. Ethyl 3,4-dihydroxybenzoate protects myocardium by activating NO synthase and generating mitochondrial ROS. Ethyl 3,4-dihydroxybenzoate induces cell autophagy and apoptosis in ESCC cells. Ethyl 3,4-dihydroxybenzoate is a collagen synthesis inhibitor and has a bone protecting-effect[1][2][3][4].

同义名列表

19 个代谢物同义名

InChI=1/C9H10O4/c1-2-13-9(12)6-3-4-7(10)8(11)5-6/h3-5,10-11H,2H2,1H; Benzoic acid, 3,4-dihydroxy-, ethyl ester; Benzoic acid,4-dihydroxy-, ethyl ester; 3,4-Dihydroxybenzoic acid, ethyl ester; 3,4-Dihydroxy-benzoic acid ethyl ester; Protocatechuic acid ethyl ester, 97\\%; 3,4-dihydroxybenzoic acid ethyl ester; Protocatechuic acid, ethyl ester; Protocatechuic acid ethyl ester; Ethyl-3,4-dihydroxy-benzoate; ethyl-3,4-dihydroxybenzoate; Ethyl 3,4-dihydroxybenzoate; ethyl protocatechuate; UNII-4YGJ96WTBG; Tox21_113836; 3,4-DHBEEOP; 4YGJ96WTBG; Ethyl; EDHB



数据库引用编号

11 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。



文献列表

  • Regina G Daré, Ana Costa, Celso V Nakamura, Maria C T Truiti, Valdecir F Ximenes, Sueli O S Lautenschlager, Bruno Sarmento. Evaluation of lipid nanoparticles for topical delivery of protocatechuic acid and ethyl protocatechuate as a new photoprotection strategy. International journal of pharmaceutics. 2020 May; 582(?):119336. doi: 10.1016/j.ijpharm.2020.119336. [PMID: 32304728]
  • Reza Farhoosh. A Kinetic Approach to Evaluate the Structure-Based Performance of Antioxidants During Lipid Oxidation. Journal of food science. 2018 Jan; 83(1):101-107. doi: 10.1111/1750-3841.13993. [PMID: 29210460]
  • Yu-Sheng Shi, Yun-Bao Liu, Shuang-Gang Ma, Yong Li, Jing Qu, Li Li, Shao-Peng Yuan, Qi Hou, Yu-Huan Li, Jian-Dong Jiang, Shi-Shan Yu. Bioactive Sesquiterpenes and Lignans from the Fruits of Xanthium sibiricum. Journal of natural products. 2015 Jul; 78(7):1526-35. doi: 10.1021/np500951s. [PMID: 26110443]
  • Yuanyuan Ma, Agnieszka Kosińska-Cagnazzo, William L Kerr, Ryszard Amarowicz, Ruthann B Swanson, Ronald B Pegg. Separation and characterization of soluble esterified and glycoside-bound phenolic compounds in dry-blanched peanut skins by liquid chromatography-electrospray ionization mass spectrometry. Journal of agricultural and food chemistry. 2014 Nov; 62(47):11488-504. doi: 10.1021/jf503836n. [PMID: 25354220]
  • Byoungjae Kim, Kyung Min Choi, Hong Soon Yim, Min-Goo Lee. Ascorbic acid enhances adipogenesis of 3T3-L1 murine preadipocyte through differential expression of collagens. Lipids in health and disease. 2013 Dec; 12(?):182. doi: 10.1186/1476-511x-12-182. [PMID: 24325571]
  • Milind M Muley, Vishnu N Thakare, Rajesh R Patil, Pallavi A Bafna, Suresh R Naik. Amelioration of cognitive, motor and endogenous defense functions with silymarin, piracetam and protocatechuic acid in the cerebral global ischemic rat model. Life sciences. 2013 Jul; 93(1):51-57. doi: 10.1016/j.lfs.2013.05.020. [PMID: 23743171]
  • Milind M Muley, Vishnu N Thakare, Rajesh R Patil, Ajay D Kshirsagar, Suresh R Naik. Silymarin improves the behavioural, biochemical and histoarchitecture alterations in focal ischemic rats: a comparative evaluation with piracetam and protocatachuic acid. Pharmacology, biochemistry, and behavior. 2012 Aug; 102(2):286-93. doi: 10.1016/j.pbb.2012.05.004. [PMID: 22584042]
  • Edwin C M Mariman, Ping Wang. Adipocyte extracellular matrix composition, dynamics and role in obesity. Cellular and molecular life sciences : CMLS. 2010 Apr; 67(8):1277-92. doi: 10.1007/s00018-010-0263-4. [PMID: 20107860]
  • Amanda Fortes Francisco, Paula Melo de Abreu Vieira, Jerusa Marilda Arantes, Maisa Silva, Maria Lúcia Pedrosa, Silvana Maria Elói-Santos, Olindo Assis Martins-Filho, Andréa Teixeira-Carvalho, Márcio Sobreira Silva Araújo, Washington Luiz Tafuri, Cláudia Martins Carneiro. Increase of reactive oxygen species by desferrioxamine during experimental Chagas' disease. Redox report : communications in free radical research. 2010; 15(4):185-90. doi: 10.1179/174329210x12650506623528. [PMID: 20663295]
  • Fan Cheng, Yuan Zhou, Kun Zou, Jun Wu. [Studies on the chemical constituents of the fruit of Xylocarpus granatum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Aug; 32(8):1220-3. doi: ". [PMID: 19960941]
  • Ravi Kant, Vishal Diwan, Amteshwar Singh Jaggi, Nirmal Singh, Dhandeep Singh. Remote renal preconditioning-induced cardioprotection: a key role of hypoxia inducible factor-prolyl 4-hydroxylases. Molecular and cellular biochemistry. 2008 May; 312(1-2):25-31. doi: 10.1007/s11010-008-9717-5. [PMID: 18273560]
  • H Kasiganesan, V Sridharan, G Wright. Prolyl hydroxylase inhibitor treatment confers whole-animal hypoxia tolerance. Acta physiologica (Oxford, England). 2007 Jun; 190(2):163-9. doi: 10.1111/j.1748-1716.2007.01676.x. [PMID: 17394573]
  • Yusuke Sawai, Jae-Hak Moon, Kanzo Sakata, Naoharu Watanabe. Effects of structure on radical-scavenging abilities and antioxidative activities of tea polyphenols: NMR analytical approach using 1,1-diphenyl-2-picrylhydrazyl radicals. Journal of agricultural and food chemistry. 2005 May; 53(9):3598-604. doi: 10.1021/jf040423a. [PMID: 15853407]
  • Christina Warnecke, Wanja Griethe, Alexander Weidemann, Jan Steffen Jürgensen, Carsten Willam, Sebastian Bachmann, Yuri Ivashchenko, Ingrid Wagner, Ulrich Frei, Michael Wiesener, Kai-Uwe Eckardt. Activation of the hypoxia-inducible factor-pathway and stimulation of angiogenesis by application of prolyl hydroxylase inhibitors. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2003 Jun; 17(9):1186-8. doi: 10.1096/fj.02-1062fje. [PMID: 12709400]
  • Shiow Chyn Huang, Gow-Chin Yen, Lee-Wen Chang, Wen-Jye Yen, Pin-Der Duh. Identification of an antioxidant, ethyl protocatechuate, in peanut seed testa. Journal of agricultural and food chemistry. 2003 Apr; 51(8):2380-3. doi: 10.1021/jf0210019. [PMID: 12670184]
  • H Kondo, R Matsuda, Y Yonezawa. Autonomous migration of human fetal skin fibroblasts into a denuded area in a cell monolayer is mediated by basic fibroblast growth factor and collagen. In vitro cellular & developmental biology. Animal. 1993 Dec; 29A(12):929-35. doi: 10.1007/bf02634231. [PMID: 8167916]
  • A Ibrahimi, F Bonino, S Bardon, G Ailhaud, C Dani. Essential role of collagens for terminal differentiation of preadipocytes. Biochemical and biophysical research communications. 1992 Sep; 187(3):1314-22. doi: 10.1016/0006-291x(92)90446-r. [PMID: 1417807]
  • H S Yun-Choi, J H Kim, J R Lee. Potential inhibitors of platelet aggregation from plant sources, III. Journal of natural products. 1987 Nov; 50(6):1059-64. doi: 10.1021/np50054a008. [PMID: 3127544]