3,4-Dihydroxybenzeneacetic acid (BioDeep_00000000447)

 

Secondary id: BioDeep_00000229588, BioDeep_00000229775, BioDeep_00000400091

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


3,4-Dihydroxyphenylacetic Acid, Monosodium Salt

化学式: C8H8O4 (168.0422568)
中文名称: 3,4-二羟基苯乙酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.03%

分子结构信息

SMILES: C1=CC(=C(C=C1CC(=O)O)O)O
InChI: InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

描述信息

3,4-Dihydroxyphenylacetic acid (DOPAC) is a phenolic acid. DOPAC is a neuronal metabolite of dopamine (DA). DA undergoes monoamine oxidase-catalyzed oxidative deamination to 3,4-dihydroxyphenylacetaldehyde (DOPAL), which is metabolized primarily into DOPAC via aldehyde dehydrogenase (ALDH2). The biotransformation of DOPAL is critical as previous studies have demonstrated this DA-derived aldehyde to be a reactive electrophile and toxic to dopaminergic cells. Known inhibitors of mitochondrial ALDH2, such as 4-hydroxy-2-nonenal (4HNE) inhibit ALDH2-mediated oxidation of the endogenous neurotoxin DOPAL. 4HNE is one of the resulting products of oxidative stress, thus linking oxidative stress to the uncontrolled production of an endogenous neurotoxin relevant to Parkinsons disease. In early-onset Parkinson disease, there is markedly reduced activities of both monoamine oxidase (MAO) A and B. The amount of DOPAC, which is produced during dopamine oxidation by MAO, is greatly reduced as a result of increased parkin overexpression. Administration of methamphetamine to animals causes loss of DA terminals in the brain and significant decreases in dopamine and dihydroxyphenylacetic acid (DOPAC) in the striatum. Renal dopamine produced in the residual tubular units may be enhanced during a sodium challenge, thus behaving appropriately as a compensatory natriuretic hormone; however, the renal dopaminergic system in patients afflicted with renal parenchymal disorders should address parameters other than free urinary dopamine, namely the urinary excretion of L-DOPA and metabolites. DOPAC is one of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements. DOPAC exhibits a considerable antiproliferative effect in LNCaP prostate cancer and HCT116 colon cancer cells. The antiproliferative activity of DOPAC may be due to its catechol structure. A similar association of the catechol moiety in the B-ring with antiproliferative activity was demonstrated for flavanones (PMID:16956664, 16455660, 8561959, 11369822, 10443478, 16365058). DOPAC can be found in Gram-positive bacteria (PMID:24752840).
3,4-Dihydroxyphenylacetic acid (DOPAC) is a metabolite of the neurotransmitter dopamine. 3,4-Dihydroxyphenylacetic acid is found in many foods, some of which are alaska blueberry, cauliflower, ucuhuba, and fox grape.
3,4-Dihydroxybenzeneacetic acid is the main neuronal metabolite of dopamine.

同义名列表

26 个代谢物同义名

3,4-Dihydroxyphenylacetic Acid, Monosodium Salt; 2-(3,4-DIHYDROXYPHENYL)ACETIC ACID; (3,4-dihydroxyphenyl)-Acetic acid; (3,4-DIHYDROXYPHENYL)ACETIC ACID; 3,4-dihydroxy-Benzeneacetic acid; 3,4-Dihydroxy-phenylacetic acid; 3,4-dihydroxyphenyl acetic acid; 3,4-Dihydroxybenzeneacetic acid; 3,4 Dihydroxyphenylacetic Acid; 3,4-dihydroxyphenylacetic acid; 3,4-Dihydroxyphenylacetic acid; 2-(3,4-dihydroxyphenyl)acetate; (3,4-Dihydroxyphenyl)acetate; 3,4-Dihydroxyphenyl acetate; 3,4-Dihydroxybenzeneacetate; Dihydroxyphenylacetic acid; 3,4-dihydroxyphenylacetate; Homoprotocatechuic acid; Dihydroxyphenylacetate; Homoprotocatechuate; Homogentisic acid; Dopacetic acid; Dopacetate; 3,4-DHPOP; DHY; HAA



数据库引用编号

23 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

33 个相关的代谢反应过程信息。

Reactome(2)

BioCyc(0)

WikiPathways(5)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(24)

PharmGKB(0)

20 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

  • Ping Tian, Wei Zhang, Kai-Yan Li, Hong-Wei Li, Kai Ma, De-En Han. [Effect of Rehmanniae Radix on depression-like behavior and hippocampal monoamine neurotransmitters of chronic unpredictable mild stress model rats]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Sep; 47(17):4691-4697. doi: 10.19540/j.cnki.cjcmm.20220421.401. [PMID: 36164876]
  • Zoe Lofft, Amel Taibi, Paraskevi Massara, Tomas Tokar, Inke Paetau-Robinson, Christina Khoo, Elena M Comelli. Cranberry Proanthocyanidin and Its Microbial Metabolite 3,4-Dihydroxyphenylacetic Acid, but Not 3-(4-Hydroxyphenyl)-Propionic Acid, Partially Reverse Pro-Inflammatory microRNA Responses in Human Intestinal Epithelial Cells. Molecular nutrition & food research. 2022 04; 66(8):e2100853. doi: 10.1002/mnfr.202100853. [PMID: 35112478]
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