3,4-Dimethoxybenzoic acid (BioDeep_00000018844)

Main id: BioDeep_00000017288

 

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


veratric acid, sodium salt, (11)C-labeled

化学式: C9H10O4 (182.057906)
中文名称: 藜芦酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=C(C=C(C=C1)C(=O)O)OC
InChI: InChI=1S/C9H10O4/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3,(H,10,11)

描述信息

3,4-dimethoxybenzoic acid, also known as veratric acid or 3,4-dimethylprotocatechuic acid, belongs to P-methoxybenzoic acids and derivatives class of compounds. Those are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. 3,4-dimethoxybenzoic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dimethoxybenzoic acid can be synthesized from benzoic acid. 3,4-dimethoxybenzoic acid is also a parent compound for other transformation products, including but not limited to, 3beta-[(O-beta-D-glucopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]cholest-5-en-22-one, 3beta-[(beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]cholest-5-en-22-one, and 3beta-[(O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosyl)oxy]-17alpha-hydroxy-16beta-[(O-(2-O-3,4-dimethoxybenzoyl-beta-D-xylopyranosyl)-(1->3)-2-O-acetyl-alpha-L-arabinopyranosyl)oxy]cholest-5-en-22-one. 3,4-dimethoxybenzoic acid can be found in coriander and olive, which makes 3,4-dimethoxybenzoic acid a potential biomarker for the consumption of these food products.
3,4-dimethoxybenzoic acid belongs to the family of M-methoxybenzoic Acids and Derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group
Veratric acid (3,4-Dimethoxybenzoic acid) is an orally active phenolic compound derived from vegetables and fruits, has antioxidant[1] and anti-inflammatory activities[3]. Veratric acid also acts as a protective agent against hypertension-associated cardiovascular remodelling[2]. Veratric acid reduces upregulated COX-2 expression, and levels of PGE2, IL-6 after UVB irradiation[3].
Veratric acid (3,4-Dimethoxybenzoic acid) is an orally active phenolic compound derived from vegetables and fruits, has antioxidant[1] and anti-inflammatory activities[3]. Veratric acid also acts as a protective agent against hypertension-associated cardiovascular remodelling[2]. Veratric acid reduces upregulated COX-2 expression, and levels of PGE2, IL-6 after UVB irradiation[3].

同义名列表

15 个代谢物同义名

veratric acid, sodium salt, (11)C-labeled; 3,4-Dimethylprotocatechuic acid; veratric acid, potassium salt; Dimethylprotocatechuic acid; 3,4-Dimethylprotocatechuate; veratric acid, sodium salt; 3,4-Dimethoxybenzoic acid; Dimethylprotocatechuate; 3,4-Dimethoxybenzoate; Veratrumenoic acid; Veratrylic acid; Veratrumenoate; veratric acid; Veratrylate; Veratrate



数据库引用编号

10 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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INOH(0)

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55 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

  • Ganesh Harini, S Shree Ganesh, Ramprasad Anushikaa, Ramanathan Bharathi, Sankaranarayanan Aravind, Kumari Vatsala, Abinaya Shanmugavadivu, Nagarajan Selvamurugan. Antiproliferative and Apoptotic Effects of pH-Responsive Veratric Acid-Loaded Polydopamine Nanoparticles in Human Triple Negative Breast Cancer Cells. Chemistry & biodiversity. 2023 Jun; 20(6):e202201006. doi: 10.1002/cbdv.202201006. [PMID: 37140976]
  • Hyun Wook Huh, Hee-Yong Song, Young-Guk Na, Minki Kim, Mingu Han, Thi Mai Anh Pham, Hyeonmin Lee, Jungkyu Suh, Seok-Jong Lee, Hong-Ki Lee, Cheong-Weon Cho. Bioanalytical Method Development and Validation of Veratraldehyde and Its Metabolite Veratric Acid in Rat Plasma: An Application for a Pharmacokinetic Study. Molecules (Basel, Switzerland). 2020 Jun; 25(12):. doi: 10.3390/molecules25122800. [PMID: 32560470]
  • Li-Jia Liu, Xiu-Hua Hu, Li-Na Guo, Ru-Feng Wang, Qi-Tao Zhao. Anti-inflammatory effect of the compounds from the flowers of Trollius chinensis. Pakistan journal of pharmaceutical sciences. 2018 Sep; 31(5):1951-1957. doi: ". [PMID: 30150194]
  • Yan Jin, Kyung Min Jeong, Jeongmi Lee, Jing Zhao, Su-Young Choi, Kwang-Soo Baek. Development and Validation of an Analytical Method Readily Applicable for Quality Control of Tabebuia impetiginosa (Taheebo) Ethanolic Extract. Journal of AOAC International. 2018 May; 101(3):695-700. doi: 10.5740/jaoacint.17-0228. [PMID: 28927490]
  • Murugesan Saravanakumar, Boobalan Raja, Jeganathan Manivannan, Thangarasu Silambarasan, Pichavaram Prahalathan, Subramanian Kumar, Santosh Kumar Mishra. Oral administration of veratric acid, a constituent of vegetables and fruits, prevents cardiovascular remodelling in hypertensive rats: a functional evaluation. The British journal of nutrition. 2015 Nov; 114(9):1385-94. doi: 10.1017/s0007114515003086. [PMID: 26346559]
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  • Yu-Shuai Peng, Li-Jia Liu, Can Zhao, Xin Yang, Chen Liu, Ru-Feng Wang. Pharmacokinetics and tissue distributions of veratric acid after intravenous administration in rats. Chinese journal of natural medicines. 2015 Jul; 13(7):535-9. doi: 10.1016/s1875-5364(15)30048-0. [PMID: 26233844]
  • Woo-Suk Choi, Yong-Bae Seo, Pyung-Gyun Shin, Woe-Yeon Kim, Sang Yeol Lee, Young-Ju Choi, Gun-Do Kim. Veratric acid inhibits iNOS expression through the regulation of PI3K activation and histone acetylation in LPS-stimulated RAW264.7 cells. International journal of molecular medicine. 2015 Jan; 35(1):202-10. doi: 10.3892/ijmm.2014.1982. [PMID: 25352364]
  • Li-Jia Liu, Xiu-Wen Wu, Ru-Feng Wang, Yu-Shuai Peng, Xin Yang, Jun-Xiu Liu. Absorption properties and mechanism of trolline and veratric acid and their implication to an evaluation of the effective components of the flowers of Trollius chinensis. Chinese journal of natural medicines. 2014 Sep; 12(9):700-4. doi: 10.1016/s1875-5364(14)60108-4. [PMID: 25263984]
  • Ming Yuan, Yan-Nan An, Ru-Feng Wang, Yi Ding, Zhen-Xiao Sun. Distribution of Two bioactive compounds in flowers of Trollius chinensis. Journal of chromatographic science. 2014 May; 52(5):466-9. doi: 10.1093/chromsci/bmt065. [PMID: 23753470]
  • Bin Zhou, Chui-Hua Kong, Yong-Hua Li, Peng Wang, Xiao-Hua Xu. Crabgrass (Digitaria sanguinalis) allelochemicals that interfere with crop growth and the soil microbial community. Journal of agricultural and food chemistry. 2013 Jun; 61(22):5310-7. doi: 10.1021/jf401605g. [PMID: 23678893]
  • Boobalan Raja, Murugesan Saravanakumar, Gopal Sathya. Veratric acid ameliorates hyperlipidemia and oxidative stress in Wistar rats fed an atherogenic diet. Molecular and cellular biochemistry. 2012 Jul; 366(1-2):21-30. doi: 10.1007/s11010-012-1278-y. [PMID: 22426778]
  • Murugesan Saravanakumar, Boobalan Raja. Effect of veratric acid on the cardiovascular risk of L-NAME-induced hypertensive rats. Journal of cardiovascular pharmacology. 2012 Jun; 59(6):553-62. doi: 10.1097/fjc.0b013e31824f9174. [PMID: 22361750]
  • Mohamed I Walash, Mohie M Kh Sharaf El-Din, Nahed M El-Enany, Manal I Eid, Shereen M Shalan. Simultaneous determination of sulpiride and mebeverine by HPLC method using fluorescence detection: application to real human plasma. Chemistry Central journal. 2012 Feb; 6(?):13. doi: 10.1186/1752-153x-6-13. [PMID: 22333299]
  • Murugesan Saravanakumar, Boobalan Raja. Veratric acid, a phenolic acid attenuates blood pressure and oxidative stress in L-NAME induced hypertensive rats. European journal of pharmacology. 2011 Dec; 671(1-3):87-94. doi: 10.1016/j.ejphar.2011.08.052. [PMID: 21937012]
  • Shaheen Faizi, Shahina Fayyaz, Samina Bano, Erum Yawar Iqbal, Lubna, Humaira Siddiqi, Aneela Naz. Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae. Journal of agricultural and food chemistry. 2011 Sep; 59(17):9080-93. doi: 10.1021/jf201611b. [PMID: 21780738]
  • Maja Jakesevic, Kjersti Aaby, Grethe-Iren A Borge, Bengt Jeppsson, Siv Ahrné, Göran Molin. Antioxidative protection of dietary bilberry, chokeberry and Lactobacillus plantarum HEAL19 in mice subjected to intestinal oxidative stress by ischemia-reperfusion. BMC complementary and alternative medicine. 2011 Jan; 11(?):8. doi: 10.1186/1472-6882-11-8. [PMID: 21272305]
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  • T Kraemer, R Wennig, H H Maurer. The antispasmodic drug mebeverine leads to positive amphetamine results by fluorescence polarization immunoassay (FPIA)--studies on the toxicological analysis of urine by FPIA and GC-MS. Journal of analytical toxicology. 2001 Jul; 25(5):333-8. doi: 10.1093/jat/25.5.333. [PMID: 11499887]
  • R G Dickinson, P V Baker, M E Franklin, W D Hooper. Facile hydrolysis of mebeverine in vitro and in vivo: negligible circulating concentrations of the drug after oral administration. Journal of pharmaceutical sciences. 1991 Oct; 80(10):952-7. doi: 10.1002/jps.2600801010. [PMID: 1784004]
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  • M M Ames, C D Selassie, L C Woodson, J A Van Loon, C Hansch, R M Weinshilboum. Thiopurine methyltransferase: structure-activity relationships for benzoic acid inhibitors and thiophenol substrates. Journal of medicinal chemistry. 1986 Mar; 29(3):354-8. doi: 10.1021/jm00153a009. [PMID: 3950915]