3-Deoxyfructose (BioDeep_00000028162)

   

human metabolite Endogenous Chemicals and Drugs


代谢物信息卡片


(4S,5R)-1,4,5,6-Tetrahydroxyhexan-2-one

化学式: C6H12O5 (164.0685)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(not specific) 3.71%

分子结构信息

SMILES: C(C(C(CO)O)O)C(=O)CO
InChI: InChI=1S/C6H12O5/c7-2-4(9)1-5(10)6(11)3-8/h5-8,10-11H,1-3H2/t5-,6+/m0/s1

描述信息

3-Deoxyglucosone (3DG) is a dicarbonyl sugar used as a marker of hyperglycemia in diabetic patients (PMID: 10491986). 3DG is naturally synthesized from the Maillard reaction. It forms after glucose reacts with primary amino groups of lysine and arginine, found in proteins. 3DG also arises via the degradation of fructose 3-phsophate (PMID: 2300805). 3DG is highly reactive toward amine groups. It reacts with amino groups of proteins and forms advanced glycation end-products (AGEs). 3DG as well as AGEs play a role in the modification and cross-linking of long-lived proteins such as crystallin and collagen, contributing to diseases such as the vascular complications of diabetes, atherosclerosis, hypertension, Alzheimers disease, inflammation, and aging (PMID: 27164965, 10491986, 9836531, 9430981). 3DG inactivates aldehyde reductase (PMID: 7827091). Aldehyde reductase is the cellular enzyme that protects the body from 3DG. Detoxification of 3DG to 3-deoxyfructose (3DF) is impaired in diabetics. Aminoguanidine (AG) is an investigational drug used to deactivate 3-DG (PMID: 8194672).

同义名列表

5 个代谢物同义名

(4S,5R)-1,4,5,6-Tetrahydroxyhexan-2-one; 3-Deoxy-D-erythro-2-hexulose; 3-Deoxy-D-erythro-hexulose; 3-Deoxyhexulose; 3-Deoxyfructose



数据库引用编号

5 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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


文献列表

  • Julia Degen, Helene Beyer, Björn Heymann, Michael Hellwig, Thomas Henle. Dietary influence on urinary excretion of 3-deoxyglucosone and its metabolite 3-deoxyfructose. Journal of agricultural and food chemistry. 2014 Mar; 62(11):2449-56. doi: 10.1021/jf405546q. [PMID: 24579887]
  • Claus Peter Schmitt, Dorothee von Heyl, Susanne Rieger, Klaus Arbeiter, Klaus Eugen Bonzel, Michel Fischbach, Joachim Misselwitz, Ann-Kathrin Pieper, Franz Schaefer. Reduced systemic advanced glycation end products in children receiving peritoneal dialysis with low glucose degradation product content. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2007 Jul; 22(7):2038-44. doi: 10.1093/ndt/gfm148. [PMID: 17420168]
  • Theeraporn Puntheeranurak, Barbara Wimmer, Francisco Castaneda, Hermann J Gruber, Peter Hinterdorfer, Rolf K H Kinne. Substrate specificity of sugar transport by rabbit SGLT1: single-molecule atomic force microscopy versus transport studies. Biochemistry. 2007 Mar; 46(10):2797-804. doi: 10.1021/bi061917z. [PMID: 17302432]
  • Gerard T Berry, John W Baynes, Kevin J Wells-Knecht, Benjamin S Szwergold, René Santer. Elements of diabetic nephropathy in a patient with GLUT 2 deficiency. Molecular genetics and metabolism. 2005 Dec; 86(4):473-7. doi: 10.1016/j.ymgme.2005.09.010. [PMID: 16288895]
  • Naila Ahmed, Paul J Thornalley. Chromatographic assay of glycation adducts in human serum albumin glycated in vitro by derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl-carbamate and intrinsic fluorescence. The Biochemical journal. 2002 May; 364(Pt 1):15-24. doi: 10.1042/bj3640015. [PMID: 11988071]
  • E D Schleicher, A Bierhaus, H U Häring, P P Nawroth, R Lehmann. Chemistry and pathobiology of advanced glycation end products. Contributions to nephrology. 2001; ?(131):1-9. doi: 10.1159/000060056. [PMID: 11125554]
  • K J Wells-Knecht, T J Lyons, D R McCance, S R Thorpe, M S Feather, J W Baynes. 3-Deoxyfructose concentrations are increased in human plasma and urine in diabetes. Diabetes. 1994 Sep; 43(9):1152-6. doi: 10.2337/diab.43.9.1152. [PMID: 8070616]
  • K J Knecht, M S Feather, J W Baynes. Detection of 3-deoxyfructose and 3-deoxyglucosone in human urine and plasma: evidence for intermediate stages of the Maillard reaction in vivo. Archives of biochemistry and biophysics. 1992 Apr; 294(1):130-7. doi: 10.1016/0003-9861(92)90146-n. [PMID: 1550339]