Pseudouridine 5'-phosphate (BioDeep_00000004601)

 

Secondary id: BioDeep_00001869288

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


{[(2R,3S,4R,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

化学式: C9H13N2O9P (324.0359)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(feces) 9.38%

分子结构信息

SMILES: C1=C(C(=O)NC(=O)N1)C2C(C(C(O2)COP(=O)(O)O)O)O
InChI: InChI=1S/C9H13N2O9P/c12-5-4(2-19-21(16,17)18)20-7(6(5)13)3-1-10-9(15)11-8(3)14/h1,4-7,12-13H,2H2,(H2,16,17,18)(H2,10,11,14,15)/t4-,5-,6-,7+/m1/s1

描述信息

Pseudouridine (5-ribosyluracil) is a ubiquitous yet enigmatic constituent of structural RNAs (transfer, ribosomal, small nuclear, and small nucleolar). Although pseudouridine (psi) was the first modified nucleoside to be discovered in RNA, and is the most abundant, its biosynthesis and biological roles have remained poorly understood since its identification as a "fifth nucleoside" in RNA. Recently, a combination of biochemical, biophysical, and genetic approaches has helped to illuminate the structural consequences of psi in polyribonucleotides, the biochemical mechanism of U-->psi isomerization in RNA, and the role of modification enzymes (psi synthases) and box H/ACA snoRNAs, a class of eukaryotic small nucleolar RNAs, in the site-specific biosynthesis of psi. Through its unique ability to coordinate a structural water molecule via its free N1-H, psi exerts a subtle but significant "rigidifying" influence on the nearby sugar-phosphate backbone and also enhances base stacking. These effects may underlie the biological role of most (but perhaps not all) of the psi residues in RNA. Certain genetic mutants lacking specific psi residues in tRNA or rRNA exhibit difficulties in translation, display slow growth rates, and fail to compete effectively with wild-type strains in mixed culture. In particular, normal growth is severely compromised in an Escherichia coli mutant deficient in a pseudouridine synthase responsible for the formation of three closely spaced psi residues in the mRNA decoding region of the 23S rRNA. Such studies demonstrate that pseudouridylation of RNA confers an important selective advantage in a natural biological context. PMID: 10902565 [HMDB]. Pseudouridine 5-phosphate is found in many foods, some of which are garland chrysanthemum, chives, broad bean, and green bell pepper.
Pseudouridine (5-ribosyluracil) is a ubiquitous yet enigmatic constituent of structural RNAs (transfer, ribosomal, small nuclear, and small nucleolar). Although pseudouridine (psi) was the first modified nucleoside to be discovered in RNA, and is the most abundant, its biosynthesis and biological roles have remained poorly understood since its identification as a "fifth nucleoside" in RNA. Recently, a combination of biochemical, biophysical, and genetic approaches has helped to illuminate the structural consequences of psi in polyribonucleotides, the biochemical mechanism of U-->psi isomerization in RNA, and the role of modification enzymes (psi synthases) and box H/ACA snoRNAs, a class of eukaryotic small nucleolar RNAs, in the site-specific biosynthesis of psi. Through its unique ability to coordinate a structural water molecule via its free N1-H, psi exerts a subtle but significant "rigidifying" influence on the nearby sugar-phosphate backbone and also enhances base stacking. These effects may underlie the biological role of most (but perhaps not all) of the psi residues in RNA. Certain genetic mutants lacking specific psi residues in tRNA or rRNA exhibit difficulties in translation, display slow growth rates, and fail to compete effectively with wild-type strains in mixed culture. In particular, normal growth is severely compromised in an Escherichia coli mutant deficient in a pseudouridine synthase responsible for the formation of three closely spaced psi residues in the mRNA decoding region of the 23S rRNA. Such studies demonstrate that pseudouridylation of RNA confers an important selective advantage in a natural biological context. PMID: 10902565.

同义名列表

15 个代谢物同义名

{[(2R,3S,4R,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid; (1S)-1,4-Anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-5-O-phosphono-D-ribitol; 5-(5-O-Phosphono-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione; 5-(5-O-Phosphono-beta-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione; 5-(5-O-Phosphono-b-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione; 5-(5-O-Phosphono-β-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione; 5-(5-O-Phosphono-β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione; Pseudouridine 5-phosphoric acid; Pseudouridine 5-phosphic acid; Pseudouridine 5-monophosphate; Pseudouridine monophosphate; Pseudouridine 5’-phosphate; Pseudouridine 5-phosphate; Pseudouridylic acid; Pseudouridine 5'-phosphate



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(2)

BioCyc(0)

PlantCyc(0)

代谢反应

65 个相关的代谢反应过程信息。

Reactome(64)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

  • Purine Degradation: Adenosine triphosphate + Pseudouridine ⟶ Adenosine diphosphate + Hydrogen Ion + Pseudouridine 5'-phosphate

PharmGKB(0)

2 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

  • Xavier Darzacq, Beáta E Jády, Céline Verheggen, Arnold M Kiss, Edouard Bertrand, Tamás Kiss. Cajal body-specific small nuclear RNAs: a novel class of 2'-O-methylation and pseudouridylation guide RNAs. The EMBO journal. 2002 Jun; 21(11):2746-56. doi: 10.1093/emboj/21.11.2746. [PMID: 12032087]