Glucosamine 6-phosphate (BioDeep_00000002694)

 

Secondary id: BioDeep_00000400039, BioDeep_00000400212

natural product human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester

化学式: C6H14NO8P (259.04570140000004)
中文名称: D-氨基葡萄糖6-磷酸, D-氨基葡萄糖6-磷酸, D-葡糖胺-6-磷酸
谱图信息: 最多检出来源 Viridiplantae(plant) 0.37%

分子结构信息

SMILES: C(C1C(C(C(C(O1)O)N)O)O)OP(=O)(O)O
InChI: InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1

描述信息

Glucosamine 6-phosphate (CAS: 3616-42-0) is normally produced in endothelial cells via de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals.It is a member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus (PMID:11270676, 11842094).
Glucosamine 6-phosphate is normally produced in endothelial cells via the de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals. A member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus. (PMID 11270676, 11842094) [HMDB]
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID G021; [MS2] KO008968
KEIO_ID G021

同义名列表

29 个代谢物同义名

Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester; {[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid; 2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranose; alpha-D-Glucosamine 6-(dihydrogen phosphoric acid); 2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranose; 2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranose; a-D-Glucosamine 6-(dihydrogen phosphoric acid); α-D-Glucosamine 6-(dihydrogen phosphoric acid); alpha-D-Glucosamine 6-(dihydrogen phosphate); 2-amino-2-deoxy-D-glucopyranose 6-phosphate; α-D-Glucosamine 6-(dihydrogen phosphate); a-D-Glucosamine 6-(dihydrogen phosphate); D-Glucosamine-6-phosphate sodium salt; 2-Amino-2-deoxy-D-glucose 6-phosphate; 2-Amino-2-deoxyglucose 6-phosphate; 2-Amino-D-glucose-6-phosphate; Glucosamine 6-phosphoric acid; α-D-glucosamine 6-phosphate; D-glucosamine 6-phosphate; Glucose-6-phosphoric acid; D-glucosamine-6-phosphate; Glucosamine 6 -phosphate; D-Glucosamine phosphate; Glucosamine 6-phosphate; Glucosamine-6-phosphate; Glucose-6-phosphorate; Glucosamine-6-P; GLCN-6-P; Glucosamine 6-phosphate



数据库引用编号

37 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(9)

BioCyc(17)

PlantCyc(0)

代谢反应

650 个相关的代谢反应过程信息。

Reactome(160)

BioCyc(124)

WikiPathways(0)

Plant Reactome(210)

INOH(3)

PlantCyc(97)

COVID-19 Disease Map(0)

PathBank(56)

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。



文献列表

  • Wongsakorn Suchaoin, Arshad Mahmood, Kesinee Netsomboon, Andreas Bernkop-Schnürch. Zeta-potential-changing nanoparticles conjugated with cell-penetrating peptides for enhanced transfection efficiency. Nanomedicine (London, England). 2017 May; 12(9):963-975. doi: 10.2217/nnm-2016-0345. [PMID: 28440703]
  • Mamoru Nozaki, Munetaka Sugiyama, Jun Duan, Hiroshi Uematsu, Tatsuya Genda, Yasushi Sato. A missense mutation in the glucosamine-6-phosphate N-acetyltransferase-encoding gene causes temperature-dependent growth defects and ectopic lignin deposition in Arabidopsis. The Plant cell. 2012 Aug; 24(8):3366-79. doi: 10.1105/tpc.112.102806. [PMID: 22932674]
  • Chang-Suk Kong, Jung-Ae Kim, Tae Kil Eom, Se-Kwon Kim. Phosphorylated glucosamine inhibits adipogenesis in 3T3-L1 adipocytes. The Journal of nutritional biochemistry. 2010 May; 21(5):438-43. doi: 10.1016/j.jnutbio.2009.01.018. [PMID: 19427183]
  • Juan Wang, Xiang Liu, Yu-He Liang, Lan-Fen Li, Xiao-Dong Su. Acceptor substrate binding revealed by crystal structure of human glucosamine-6-phosphate N-acetyltransferase 1. FEBS letters. 2008 Sep; 582(20):2973-8. doi: 10.1016/j.febslet.2008.07.040. [PMID: 18675810]
  • Cong Liu, Dan Li, Yu-He Liang, Lan-Fen Li, Xiao-Dong Su. Ring-opening mechanism revealed by crystal structures of NagB and its ES intermediate complex. Journal of molecular biology. 2008 May; 379(1):73-81. doi: 10.1016/j.jmb.2008.03.031. [PMID: 18436239]
  • Davis W Cheng, Yan Jiang, Anath Shalev, Renu Kowluru, Errol D Crook, Lalit P Singh. An analysis of high glucose and glucosamine-induced gene expression and oxidative stress in renal mesangial cells. Archives of physiology and biochemistry. 2006 Oct; 112(4-5):189-218. doi: 10.1080/13813450601093518. [PMID: 17178593]
  • Lalit P Singh, Kenneith Green, Michelle Alexander, Shira Bassly, Errol D Crook. Hexosamines and TGF-beta1 use similar signaling pathways to mediate matrix protein synthesis in mesangial cells. American journal of physiology. Renal physiology. 2004 Feb; 286(2):F409-16. doi: 10.1152/ajprenal.00007.2003. [PMID: 14559714]
  • E D Crook, S T Simmons, M Daniels, L P Singh. Regulation of glutamine:fructose-6-phosphate amidotransferase activity by high glucose and transforming growth factor beta in rat mesangial cells. Journal of investigative medicine : the official publication of the American Federation for Clinical Research. 2000 Nov; 48(6):427-34. doi: NULL. [PMID: 11094865]
  • R Lara-Lemus, M L Calcagno. Glucosamine-6-phosphate deaminase from beef kidney is an allosteric system of the V-type. Biochimica et biophysica acta. 1998 Oct; 1388(1):1-9. doi: 10.1016/s0167-4838(98)00141-1. [PMID: 9774701]
  • J K Roberts, N Wade-Jardetzky, O Jardetzky. Intracellular pH measurements by 31P nuclear magnetic resonance. Influence of factors other than pH on 31P chemical shifts. Biochemistry. 1981 Sep; 20(19):5389-94. doi: 10.1021/bi00522a006. [PMID: 7295683]