3,7-Dimethyluric acid (BioDeep_00000001228)

 

Secondary id: BioDeep_00000405493

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


3,7-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

化学式: C7H8N4O3 (196.0596)
中文名称: 3,7-二甲基尿酸
谱图信息: 最多检出来源 Homo sapiens(blood) 20.39%

分子结构信息

SMILES: CN1C(=O)NC2=C1C(=O)NC(=O)N2C
InChI: InChI=1S/C7H8N4O3/c1-10-3-4(8-6(10)13)11(2)7(14)9-5(3)12/h1-2H3,(H,8,13)(H,9,12,14)

描述信息

3,7-Dimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 3,7-Dimethyluric is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316, 15833286, 3506820, 15013152) [HMDB]
3,7-Dimethyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 3,7-Dimethyluric is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis (PMID:11712316, 15833286, 3506820, 15013152).

同义名列表

13 个代谢物同义名

3,7-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione; 3,7-Dimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione; 3,7-Dimethyl-2,6,8-trihydroxypurine; 3,7-dimethyl-9H-purine-2,6,8-trione; 3,7-Dimethyluric acid; 37-Dimethyluric acid; 3,7-Dimethylic acid; 37-Dimethylic acid; 3,7-Dimethylate; 37-Dimethylate; 3,7-DMU; 3,7-Dimethyluric acid; 3,7-Dimethyluric acid



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

7 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(5)

  • Caffeine Metabolism: Oxygen + Paraxanthine + Water ⟶ 1,7-Dimethyluric acid + Hydrogen peroxide
  • Caffeine Metabolism: Oxygen + Paraxanthine + Water ⟶ 1,7-Dimethyluric acid + Hydrogen peroxide
  • Caffeine Metabolism: Oxygen + Paraxanthine + Water ⟶ 1,7-Dimethyluric acid + Hydrogen peroxide
  • Caffeine Metabolism: Oxygen + Paraxanthine + Water ⟶ 1,7-Dimethyluric acid + Hydrogen peroxide
  • Caffeine Metabolism: Oxygen + Paraxanthine + Water ⟶ 1,7-Dimethyluric acid + Hydrogen peroxide

PharmGKB(0)

16 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。

亚细胞结构定位 关联基因列表
Cytoplasm 2 CYP2E1, XDH
Peripheral membrane protein 1 CYP2E1
Endoplasmic reticulum membrane 3 CYP1A2, CYP2E1, TMX1
Mitochondrion membrane 1 TMX1
Nucleus 2 CBX4, ERH
cytosol 1 XDH
mitochondrial membrane 1 TMX1
nuclear body 1 CBX4
nucleoplasm 1 CBX4
Cell membrane 1 TNF
cell surface 1 TNF
Golgi membrane 1 INS
mitochondrial inner membrane 1 CYP2E1
neuronal cell body 1 TNF
plasma membrane 1 TNF
Membrane 1 TMX1
endoplasmic reticulum 1 TMX1
extracellular space 4 IL10, INS, TNF, XDH
intracellular membrane-bounded organelle 2 CYP1A2, CYP2E1
Microsome membrane 2 CYP1A2, CYP2E1
Single-pass type I membrane protein 1 TMX1
Secreted 3 IL10, INS, TMX1
extracellular region 4 IL10, INS, TMX1, TNF
external side of plasma membrane 1 TNF
midbody 1 ERH
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Mitochondrion inner membrane 1 CYP2E1
Membrane raft 1 TNF
Peroxisome 1 XDH
sarcoplasmic reticulum 1 XDH
nuclear speck 1 CBX4
phagocytic cup 1 TNF
Endomembrane system 1 TMX1
endosome lumen 1 INS
mitochondria-associated endoplasmic reticulum membrane contact site 1 TMX1
Nucleus speckle 1 CBX4
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
PcG protein complex 1 CBX4
PRC1 complex 1 CBX4
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
methylosome 1 ERH
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Miquel Rojas-Cherto, Julio E Peironcely, Piotr T Kasper, Justin J J van der Hooft, Ric C H de Vos, Rob Vreeken, Thomas Hankemeier, Theo Reijmers. Metabolite identification using automated comparison of high-resolution multistage mass spectral trees. Analytical chemistry. 2012 Jul; 84(13):5524-34. doi: 10.1021/ac2034216. [PMID: 22612383]
  • Hideo Nakabayashi, Takashi Hashimoto, Hitoshi Ashida, Shin Nishiumi, Kazuki Kanazawa. Inhibitory effects of caffeine and its metabolites on intracellular lipid accumulation in murine 3T3-L1 adipocytes. BioFactors (Oxford, England). 2008; 34(4):293-302. doi: 10.3233/bio-2009-1083. [PMID: 19850984]
  • O O Akinyinka, A Sowunmi, R Honeywell, A G Renwick. Urinary recovery of caffeine and its metabolites in healthy African children. African journal of medicine and medical sciences. 2001 Mar; 30(1-2):1-4. doi: . [PMID: 14510139]
  • S Gates, J O Miners. Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism. British journal of clinical pharmacology. 1999 Mar; 47(3):299-305. doi: 10.1046/j.1365-2125.1999.00890.x. [PMID: 10215755]
  • L Fraisse, J B Verlhac, B Roche, M C Rascle, A Rabion, J L Seris. Long-chain-substituted uric acid and 5,6-diaminouracil derivatives as novel agents against free radical processes: synthesis and in vitro activity. Journal of medicinal chemistry. 1993 May; 36(10):1465-73. doi: 10.1021/jm00062a020. [PMID: 8496914]