Dihydroorotic acid (BioDeep_00000001339)

 

Secondary id: BioDeep_00000027870, BioDeep_00000399870, BioDeep_00000415841

natural product human metabolite PANOMIX_OTCML-2023 Endogenous Chemicals and Drugs


代谢物信息卡片


(S)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid

化学式: C5H6N2O4 (158.0327556)
中文名称: 二氢-DL-乳清酸, L-氢化乳清酸, 2,6-二氧代六氢嘧啶-4-羧酸, 氢化乳清酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.5%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Dihydroorotic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/dihydroorotic_acid (retrieved 2024-11-10) (BioDeep RN: BioDeep_00000001339). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1C(NC(=O)NC1=O)C(=O)O
InChI: InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)

描述信息

4,5-Dihydroorotic acid, also known as dihydroorotate or hydroorotate is a pyrimidinemonocarboxylic acid that results from the base-catalysed cyclisation of N-alpha-carbethoxyasparagine. It is classified as a secondary amide, a monocarboxylic acid, a pyrimidinemonocarboxylic acid and a N-acylurea. 4,5-Dihydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis. 4,5-Dihydroorotic acid exists in all living species, ranging from bacteria to plants to humans. 4,5-Dihydroorotic acid is synthesized by the enzyme known as Dihydroorotase (EC 3.5.2.3) which converts carbamoyl aspartic acid into 4,5-dihydroorotic acid as part of the de novo pyrimidine biosynthesis pathway (PMID: 13163076). 4,5-Dihydroorotic acid is also a substrate for the enzyme known as dihydroorotate dehydrogenase (DHODH). In mammalian species, DHODH catalyzes the fourth step in the de novo pyrimidine biosynthesis pathway, which involves the ubiquinone-mediated oxidation of dihydroorotate to orotate and the reduction of flavin mononucleotide (FMN) to dihydroflavin mononucleotide (FMNH2). Inhibition of DHODH activity with teriflunomide (an immunomodulatory drug) or expression with RNA interference results in reduced ROS generation and consequent apoptosis of transformed skin and prostate epithelial cells. Mutations in the DHOD gene have been shown to cause Miller syndrome, also known as Genee-Wiedemann syndrome, Wildervanck-Smith syndrome or post-axial acrofacial dystosis (PMID: 19915526).
4,5-Dihydroorotic acid is a substrate of the enzyme orotate reductase [EC 1.3.1.14], which is part of the pyrimidine metabolism pathway. (KEGG) Dihydroorotate is oxidized by Dihydroorotate dehydrogenases (DHODs) to orotate. These dehydrogenases use their FMN (flavin mononucleotide) prosthetic group to abstract a hydride equivalent from C6 to deprotonate C5 [HMDB]
L-Dihydroorotic acid can reversibly hydrolyze to yield the acyclic L-ureidosuccinic acid by dihydrowhey enzyme[1].

同义名列表

35 个代谢物同义名

(S)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid; (R)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid; (+)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid; (R)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate; 2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid; (+)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate; (S)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate; (4S)-2,6-dioxo-1,3-diazinane-4-carboxylic acid; 2,6-Dioxohexahydro-4-pyrimidinecarboxylic acid; 2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate; 2,6-dioxo-1,3-diazinane-4-carboxylic acid; 4,5-Dihydroorotic acid, (DL)-isomer; 4,5-Dihydroorotic acid, (D)-isomer; 4,5-Dihydroorotic acid, (L)-isomer; 5,6-Dihydro-orotic acid; (S)-4,5-Dihydroorotate; 4,5-Dihydroorotic acid; DL-Dihydroortotic acid; DL-Dihydroorotic acid; Dihydro-L-orotic acid; L-Dihydroorotic acid; 5,6-Dihydro-orotate; (S)-Dihydroorotate; L-Hydroorotic acid; 4,5-Dihydroorotate; DL-Dihydroortotate; 5,6-Dihydroorotate; dihydroorotic acid; hydroorotic acid; R,S-Hydroorotate; L-Dihydroorotate; Dihydroorotate; L-Hydroorotate; Hydroorotate; 4,5-Dihydroorotic acid



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(1)

BioCyc(0)

PlantCyc(0)

代谢反应

37 个相关的代谢反应过程信息。

Reactome(13)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(3)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(21)

PharmGKB(0)

5 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

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