Dyspropterin (BioDeep_00000005282)

 

Secondary id: BioDeep_00000840879, BioDeep_00001869217, BioDeep_00001872771

human metabolite Endogenous


代谢物信息卡片


1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione

化学式: C9H11N5O3 (237.0862)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(natural_products) 20.41%

分子结构信息

SMILES: CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(=N2)N
InChI: InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17)

描述信息

Dyspropterin, an intermediate formed from dihydroneopterin triphosphate in the biosynthetic pathway of tetrahydrobiopterin. [HMDB]
Dyspropterin, an intermediate formed from dihydroneopterin triphosphate in the biosynthetic pathway of tetrahydrobiopterin.

同义名列表

9 个代谢物同义名

1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione; 1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione; 6-(1,2-Dioxopropyl)-5,6,7,8-tetrahydropterin; 6-Pyruvoyl-5,6,7,8-tetrahydropterin; 6-Pyruvoyl tetrahydropteridine; 6-Pyruvoyl-tetrahydropterin; 6-Pyruvoyltetrahydropterin; Pyruvoyl-H4-pterin; Dyspropterin



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(1)

PlantCyc(0)

代谢反应

58 个相关的代谢反应过程信息。

Reactome(56)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

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

  • Yi-Chen Liao, Ying-Ho Lee, Lea-Yea Chuang, Jinn-Yuh Guh, Ming-Der Shi, Jau-Shyang Huang. Advanced glycation end products-mediated hypertrophy is negatively regulated by tetrahydrobiopterin in renal tubular cells. Molecular and cellular endocrinology. 2012 May; 355(1):71-7. doi: 10.1016/j.mce.2012.01.018. [PMID: 22326994]
  • Cheul Ho Park, Jae Woo Kim. Effect of advanced glycation end products on oxidative stress and senescence of trabecular meshwork cells. Korean journal of ophthalmology : KJO. 2012 Apr; 26(2):123-31. doi: 10.3341/kjo.2012.26.2.123. [PMID: 22511839]
  • Lena A Basile, Dolph Ellefson, Zoya Gluzman-Poltorak, Katiana Junes-Gill, Vernon Mar, Sarita Mendonca, Joseph D Miller, Jamie Tom, Alice Trinh, Timothy K Gallaher. HemaMax™, a recombinant human interleukin-12, is a potent mitigator of acute radiation injury in mice and non-human primates. PloS one. 2012; 7(2):e30434. doi: 10.1371/journal.pone.0030434. [PMID: 22383962]
  • Hongchao Wang, Bo Yang, Guangfei Hao, Yun Feng, Haiqin Chen, Lu Feng, Jianxin Zhao, Hao Zhang, Yong Q Chen, Lei Wang, Wei Chen. Biochemical characterization of the tetrahydrobiopterin synthesis pathway in the oleaginous fungus Mortierella alpina. Microbiology (Reading, England). 2011 Nov; 157(Pt 11):3059-3070. doi: 10.1099/mic.0.051847-0. [PMID: 21852350]
  • Rio P Juni, An L Moens. Role of sepiapterin on endothelial nitric oxide synthase in acute kidney injury: an enigmatic story. Journal of cardiovascular pharmacology. 2011 Sep; 58(3):335; author reply 335-336. doi: 10.1097/fjc.0b013e31822ba174. [PMID: 21897153]
  • Hiromi Jo, Hajime Otani, Fusakazu Jo, Takayuki Shimazu, Toru Okazaki, Kei Yoshioka, Masanori Fujita, Atsushi Kosaki, Toshiji Iwasaka. Inhibition of nitric oxide synthase uncoupling by sepiapterin improves left ventricular function in streptozotocin-induced diabetic mice. Clinical and experimental pharmacology & physiology. 2011 Aug; 38(8):485-93. doi: 10.1111/j.1440-1681.2011.05535.x. [PMID: 21554376]
  • Matthieu Legrand, Asli Kandil, Didier Payen, Can Ince. Effects of sepiapterin infusion on renal oxygenation and early acute renal injury after suprarenal aortic clamping in rats. Journal of cardiovascular pharmacology. 2011 Aug; 58(2):192-8. doi: 10.1097/fjc.0b013e31821f8ec3. [PMID: 21562427]
  • Amy L Sindler, Bradley S Fleenor, John W Calvert, Kurt D Marshall, Melanie L Zigler, David J Lefer, Douglas R Seals. Nitrite supplementation reverses vascular endothelial dysfunction and large elastic artery stiffness with aging. Aging cell. 2011 Jun; 10(3):429-37. doi: 10.1111/j.1474-9726.2011.00679.x. [PMID: 21276184]
  • Catherine A Lemarié, Layla Shbat, Chiara Marchesi, Orlando J Angulo, Marie-Eve Deschênes, Mark D Blostein, Pierre Paradis, Ernesto L Schiffrin. Mthfr deficiency induces endothelial progenitor cell senescence via uncoupling of eNOS and downregulation of SIRT1. American journal of physiology. Heart and circulatory physiology. 2011 Mar; 300(3):H745-53. doi: 10.1152/ajpheart.00321.2010. [PMID: 21169404]
  • Manju A Kurian, Yan Li, Juan Zhen, Esther Meyer, Nebula Hai, Hans-Jürgen Christen, Georg F Hoffmann, Philip Jardine, Arpad von Moers, Santosh R Mordekar, Finbar O'Callaghan, Evangeline Wassmer, Elizabeth Wraige, Christa Dietrich, Timothy Lewis, Keith Hyland, Simon Heales, Terence Sanger, Paul Gissen, Birgit E Assmann, Maarten E A Reith, Eamonn R Maher. Clinical and molecular characterisation of hereditary dopamine transporter deficiency syndrome: an observational cohort and experimental study. The Lancet. Neurology. 2011 Jan; 10(1):54-62. doi: 10.1016/s1474-4422(10)70269-6. [PMID: 21112253]
  • Akiko Ohashi, Yuko Sugawara, Kaori Mamada, Yoshinori Harada, Tomomi Sumi, Naohiko Anzai, Shin Aizawa, Hiroyuki Hasegawa. Membrane transport of sepiapterin and dihydrobiopterin by equilibrative nucleoside transporters: a plausible gateway for the salvage pathway of tetrahydrobiopterin biosynthesis. Molecular genetics and metabolism. 2011 Jan; 102(1):18-28. doi: 10.1016/j.ymgme.2010.09.005. [PMID: 20956085]
  • Yoon-Jung Moon, Eun-Mi Lee, Young Mok Park, Young Shik Park, Won-Il Chung, Young-Ho Chung. The role of cyanopterin in UV/blue light signal transduction of cyanobacterium Synechocystis sp. PCC 6803 phototaxis. Plant & cell physiology. 2010 Jun; 51(6):969-80. doi: 10.1093/pcp/pcq059. [PMID: 20418333]
  • Mya Thida, John Earl, Yan Zhao, Hans Wang, Chi S Tse, Janine J Vickers, Matthew Sutton, Sharon L H Ong, Trevor A Mori, Kevin D Croft, Judith A Whitworth, Yi Zhang. Effects of sepiapterin supplementation and NOS inhibition on glucocorticoid-induced hypertension. American journal of hypertension. 2010 May; 23(5):569-74. doi: 10.1038/ajh.2010.27. [PMID: 20186125]
  • Smaranda Leu-Semenescu, Isabelle Arnulf, Caroline Decaix, Fathi Moussa, Fabienne Clot, Camille Boniol, Yvan Touitou, Richard Levy, Marie Vidailhet, Emmanuel Roze. Sleep and rhythm consequences of a genetically induced loss of serotonin. Sleep. 2010 Mar; 33(3):307-14. doi: 10.1093/sleep/33.3.307. [PMID: 20337188]
  • Richard E Frye. Central tetrahydrobiopterin concentration in neurodevelopmental disorders. Frontiers in neuroscience. 2010; 4(?):52. doi: 10.3389/fnins.2010.00052. [PMID: 20661295]
  • Haruka Hirakawa, Hiroshi Sawada, Yumi Yamahama, Shin-Ichiro Takikawa, Haruo Shintaku, Akira Hara, Keisuke Mase, Tomoyoshi Kondo, Teruhiko Iino. Expression analysis of the aldo-keto reductases involved in the novel biosynthetic pathway of tetrahydrobiopterin in human and mouse tissues. Journal of biochemistry. 2009 Jul; 146(1):51-60. doi: 10.1093/jb/mvp042. [PMID: 19273550]
  • Nicola Longo. Disorders of biopterin metabolism. Journal of inherited metabolic disease. 2009 Jun; 32(3):333-42. doi: 10.1007/s10545-009-1067-2. [PMID: 19234759]
  • Galen M Pieper, Irina A Ionova, Brian C Cooley, Raymond Q Migrino, Ashwani K Khanna, Jennifer Whitsett, Jeannette Vásquez-Vivar. Sepiapterin decreases acute rejection and apoptosis in cardiac transplants independently of changes in nitric oxide and inducible nitric-oxide synthase dimerization. The Journal of pharmacology and experimental therapeutics. 2009 Jun; 329(3):890-9. doi: 10.1124/jpet.108.148569. [PMID: 19307452]
  • Shubhangi K Pingle, Rajani G Tumane, Aruna A Jawade. Neopterin: Biomarker of cell-mediated immunity and potent usage as biomarker in silicosis and other occupational diseases. Indian journal of occupational and environmental medicine. 2008 Dec; 12(3):107-11. doi: 10.4103/0019-5278.44690. [PMID: 20040967]
  • Marcel M Verbeek, Michel A A P Willemsen, Ron A Wevers, Aart J Lagerwerf, Nico G G M Abeling, Nenad Blau, Beat Thöny, Euthymia Vargiami, Dimitrios I Zafeiriou. Two Greek siblings with sepiapterin reductase deficiency. Molecular genetics and metabolism. 2008 Aug; 94(4):403-409. doi: 10.1016/j.ymgme.2008.04.003. [PMID: 18502672]
  • Shi Meng, Soojin Ryu, Bin Zhao, Dao-Qi Zhang, Wolfgang Driever, Douglas G McMahon. Targeting retinal dopaminergic neurons in tyrosine hydroxylase-driven green fluorescent protein transgenic zebrafish. Molecular vision. 2008; 14(?):2475-83. doi: NULL. [PMID: 19112533]
  • Jennifer Whitsett, Matthew J Picklo, Jeannette Vasquez-Vivar. 4-Hydroxy-2-nonenal increases superoxide anion radical in endothelial cells via stimulated GTP cyclohydrolase proteasomal degradation. Arteriosclerosis, thrombosis, and vascular biology. 2007 Nov; 27(11):2340-7. doi: 10.1161/atvbaha.107.153742. [PMID: 17872449]
  • Phillip L Pearl, Jacob L Taylor, Stacey Trzcinski, Alex Sokohl. The pediatric neurotransmitter disorders. Journal of child neurology. 2007 May; 22(5):606-16. doi: 10.1177/0883073807302619. [PMID: 17690069]
  • John W Elrod, Mark R Duranski, Will Langston, James J M Greer, Ling Tao, Tammy R Dugas, Christopher G Kevil, Hunter C Champion, David J Lefer. eNOS gene therapy exacerbates hepatic ischemia-reperfusion injury in diabetes: a role for eNOS uncoupling. Circulation research. 2006 Jul; 99(1):78-85. doi: 10.1161/01.res.0000231306.03510.77. [PMID: 16763164]
  • Jan-Zhong Sheng, Dianna Wang, Andrew P Braun. DAF-FM (4-amino-5-methylamino-2',7'-difluorofluorescein) diacetate detects impairment of agonist-stimulated nitric oxide synthesis by elevated glucose in human vascular endothelial cells: reversal by vitamin C and L-sepiapterin. The Journal of pharmacology and experimental therapeutics. 2005 Nov; 315(2):931-40. doi: 10.1124/jpet.105.087932. [PMID: 16093274]
  • Gregory F Oxenkrug, Pura J Requintina. N-acetyldopamine inhibits rat brain lipid peroxidation induced by lipopolysaccharide. Annals of the New York Academy of Sciences. 2005 Aug; 1053(?):394-9. doi: 10.1111/j.1749-6632.2005.tb00047.x. [PMID: 16179545]
  • Gregory Oxenkrug. Antioxidant effects of N-acetylserotonin: possible mechanisms and clinical implications. Annals of the New York Academy of Sciences. 2005 Aug; 1053(?):334-47. doi: 10.1196/annals.1344.029. [PMID: 16179540]
  • Xiao-Wu Qu, Larry G Thaete, Ranna A Rozenfeld, Yaqin Zhu, Isabelle G De Plaen, Michael S Caplan, Wei Hsueh. Tetrahydrobiopterin prevents platelet-activating factor-induced intestinal hypoperfusion and necrosis: Role of neuronal nitric oxide synthase. Critical care medicine. 2005 May; 33(5):1050-6. doi: 10.1097/01.ccm.0000162908.14887.36. [PMID: 15891335]
  • Malarvannan Pannirselvam, William B Wiehler, Todd Anderson, Chris R Triggle. Enhanced vascular reactivity of small mesenteric arteries from diabetic mice is associated with enhanced oxidative stress and cyclooxygenase products. British journal of pharmacology. 2005 Apr; 144(7):953-60. doi: 10.1038/sj.bjp.0706121. [PMID: 15685205]
  • Greg J Dusting, Chris Triggle. Are we over oxidized? Oxidative stress, cardiovascular disease, and the future of intervention studies with antioxidants. Vascular health and risk management. 2005; 1(2):93-7. doi: 10.2147/vhrm.1.2.93.64080. [PMID: 17315394]
  • Denise M McDonald, Nicholas J Alp, Keith M Channon. Functional comparison of the endothelial nitric oxide synthase Glu298Asp polymorphic variants in human endothelial cells. Pharmacogenetics. 2004 Dec; 14(12):831-9. doi: 10.1097/00008571-200412000-00006. [PMID: 15608562]
  • Qing Xu, David A Wink, Carol A Colton. Nitric oxide production and regulation of neuronal NOS in tyrosine hydroxylase containing neurons. Experimental neurology. 2004 Aug; 188(2):341-50. doi: 10.1016/j.expneurol.2004.04.016. [PMID: 15246834]
  • Lina Elzaouk, Stephanie Laufs, Dirk Heerklotz, Walter Leimbacher, Nenad Blau, Annette Résibois, Beat Thöny. Nuclear localization of tetrahydrobiopterin biosynthetic enzymes. Biochimica et biophysica acta. 2004 Jan; 1670(1):56-68. doi: 10.1016/j.bbagen.2003.10.015. [PMID: 14729142]
  • Christiane P Tiefenbacher, Ching-Hua Lee, Jolanthe Kapitza, Volker Dietz, Feraydoon Niroomand. Sepiapterin reduces postischemic injury in the rat heart. Pflugers Archiv : European journal of physiology. 2003 Oct; 447(1):1-7. doi: 10.1007/s00424-003-1131-y. [PMID: 12905031]
  • Malarvannan Pannirselvam, Valerie Simon, Subodh Verma, Todd Anderson, Chris R Triggle. Chronic oral supplementation with sepiapterin prevents endothelial dysfunction and oxidative stress in small mesenteric arteries from diabetic (db/db) mice. British journal of pharmacology. 2003 Oct; 140(4):701-6. doi: 10.1038/sj.bjp.0705476. [PMID: 14534153]
  • Nenad Blau, Beat Thöny. Possible impact of tetrahydrobiopterin and sepiapterin on endothelial dysfunction. Arteriosclerosis, thrombosis, and vascular biology. 2003 May; 23(5):913-4; author reply 914. doi: 10.1161/01.atv.0000068647.92130.0d. [PMID: 12740227]
  • Zsolt Bagi, Akos Koller. Lack of nitric oxide mediation of flow-dependent arteriolar dilation in type I diabetes is restored by sepiapterin. Journal of vascular research. 2003 Jan; 40(1):47-57. doi: 10.1159/000068938. [PMID: 12644725]
  • Janet Rowe, Suzanne Campbell, Eileen D M Gallery. Nitric oxide production by decidual endothelial cells is not reduced in preeclampsia. Hypertension in pregnancy. 2003; 22(1):63-75. doi: 10.1081/prg-120017005. [PMID: 12648444]
  • Nada Tomic-Carruthers, Robert Mangan, Raymond Carruthers. Age estimation of Mexican fruit fly (Diptera: Tephritidae) based on accumulation of pterins. Journal of economic entomology. 2002 Dec; 95(6):1319-25. doi: 10.1603/0022-0493-95.6.1319. [PMID: 12539849]
  • Albert Huisman, Ingrid Vos, Ernst E van Faassen, Jaap A Joles, Hermann-Josef Gröne, Pavel Martasek, Anton-Jan van Zonneveld, Anatoly F Vanin, Ton J Rabelink. Anti-inflammatory effects of tetrahydrobiopterin on early rejection in renal allografts: modulation of inducible nitric oxide synthase. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2002 Jul; 16(9):1135-7. doi: 10.1096/fj.01-0890fje. [PMID: 12039851]
  • H Shintaku. Disorders of tetrahydrobiopterin metabolism and their treatment. Current drug metabolism. 2002 Apr; 3(2):123-31. doi: 10.2174/1389200024605145. [PMID: 12003346]
  • N Blau, L Bonafé, B Thöny. Tetrahydrobiopterin deficiencies without hyperphenylalaninemia: diagnosis and genetics of dopa-responsive dystonia and sepiapterin reductase deficiency. Molecular genetics and metabolism. 2001 Sep; 74(1-2):172-85. doi: 10.1006/mgme.2001.3213. [PMID: 11592814]
  • L Bonafé, B Thöny, J M Penzien, B Czarnecki, N Blau. Mutations in the sepiapterin reductase gene cause a novel tetrahydrobiopterin-dependent monoamine-neurotransmitter deficiency without hyperphenylalaninemia. American journal of human genetics. 2001 Aug; 69(2):269-77. doi: 10.1086/321970. [PMID: 11443547]
  • J Pietz, U K Meyding-Lamadé, H Schmidt. Magnetic resonance imaging of the brain in adolescents with phenylketonuria and in one case of 6-pyruvoyl tetrahydropteridine synthase deficiency. European journal of pediatrics. 1996 Jul; 155 Suppl 1(?):S69-73. doi: 10.1007/pl00014255. [PMID: 8828614]
  • A Niederwieser, H Shintaku, W Leimbacher, H C Curtius, J Hyànek, J Zeman, W Endres. "Peripheral" tetrahydrobiopterin deficiency with hyperphenylalaninaemia due to incomplete 6-pyruvoyl tetrahydropterin synthase deficiency or heterozygosity. European journal of pediatrics. 1987 May; 146(3):228-32. doi: 10.1007/bf00716465. [PMID: 3297709]
  • . . . . doi: . [PMID: 19130291]