7,8-Dihydroneopterin (BioDeep_00000017784)

 

Secondary id: BioDeep_00000001274, BioDeep_00001868732

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2-Amino-4-hydroxy-6-(D-erythro-1’,2’,3’-trihydroxypropyl)-7,8-dihydropteridine

化学式: C9H13N5O4 (255.0967498)
中文名称: 7,8-二氢-D-新蝶呤
谱图信息: 最多检出来源 Homo sapiens(blood) 6.28%

分子结构信息

SMILES: C1C(=NC2=C(N1)N=C(NC2=O)N)C(C(CO)O)O
InChI: InChI=1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)

描述信息

7,8-Dihydroneopterin, also known as dihydroneopterin, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are synthesized in several parts of the body, including the pineal gland. 7,8-Dihydroneopterin is a strong basic compound (based on its pKa). Within humans, 7,8-dihydroneopterin participates in a number of enzymatic reactions. In particular, 7,8-dihydroneopterin can be biosynthesized from sepiapterin; which is catalyzed by the enzyme sepiapterin reductase or carbonyl reductase [NADPH] 1. In humans, 7,8-dihydroneopterin is involved in the metabolic disorder called hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase (PTPS) deficiency. 7,8-Dihydroneopterin is produced by human monocyte-derived macrophages upon stimulation with interferon-gamma. Increased amounts of 7,8-dihydroneopterin in human body fluids are found in many disorders, including viral infections and autoimmune diseases (PMID: 12804528).
7,8-dihydroneopterin, also known as npr, belongs to biopterins and derivatives class of compounds. Those are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland. 7,8-dihydroneopterin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 7,8-dihydroneopterin can be found in a number of food items such as prickly pear, star anise, cocoa bean, and black salsify, which makes 7,8-dihydroneopterin a potential biomarker for the consumption of these food products. 7,8-dihydroneopterin exists in all living organisms, ranging from bacteria to humans. In humans, 7,8-dihydroneopterin is involved in the pterine biosynthesis. 7,8-dihydroneopterin is also involved in several metabolic disorders, some of which include hyperphenylalaninemia due to dhpr-deficiency, sepiapterin reductase deficiency, dopa-responsive dystonia, and hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiency.
7,8-Dihydroneopterin, an inflammation marker, induces cellular apoptosis in astrocytes and neurons via enhancement of nitric oxide synthase (iNOS) expression. 7,8-Dihydroneopterin can be used in the research of neurodegenerative diseases[1].

同义名列表

12 个代谢物同义名

2-Amino-4-hydroxy-6-(D-erythro-1’,2’,3’-trihydroxypropyl)-7,8-dihydropteridine; 2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one; 2-Amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine; 2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydro-1H-pteridin-4-one; 2-Amino-7,8-dihydro-6-[(1S,2R)-1,2,3-trihydroxypropyl]-4(3H)-pteridinone; 2-AMINO-7,8-dihydro-6-(1,2,3-trihydroxypropyl)-4(1H)-pteridinone; 7,8-Dihydro-D-erythro-neopterin; D-Erythro-7,8-dihydroneopterin; 7,8-dihydro-D-neopterin; 7,8-Dihydro-neopterin; 7,8-Dihydroneopterin; Dihydroneopterin



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(4)

PlantCyc(0)

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)

3 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

  • Nooshin Ghodsian, Anthony Yeandle, Barry D Hock, Steven P Gieseg. CD36 down regulation by the macrophage antioxidant 7,8-dihydroneopterin through modulation of PPAR-γ activity. Free radical research. 2022 May; 56(5-6):366-377. doi: 10.1080/10715762.2022.2114904. [PMID: 36017639]
  • Nooshin Ghodsian, Anthony Yeandle, Steven P Gieseg. Foam cell formation but not oxLDL cytotoxicity is inhibited by CD36 down regulation by the macrophage antioxidant 7,8-dihydroneopterin. The international journal of biochemistry & cell biology. 2021 04; 133(?):105918. doi: 10.1016/j.biocel.2021.105918. [PMID: 33421634]
  • Brian J Koos, Jeffrey A Gornbein. Early pregnancy metabolites predict gestational diabetes mellitus: implications for fetal programming. American journal of obstetrics and gynecology. 2021 02; 224(2):215.e1-215.e7. doi: 10.1016/j.ajog.2020.07.050. [PMID: 32739399]
  • Gregory Baxter-Parker, Lloyd Roffe, Sean Cross, Chris Frampton, Gary J Hooper, Steven P Gieseg. Knee replacement surgery significantly elevates the urinary inflammatory biomarkers neopterin and 7,8-dihydroneopterin. Clinical biochemistry. 2019 Jan; 63(?):39-45. doi: 10.1016/j.clinbiochem.2018.11.002. [PMID: 30399370]
  • Angus Lindsay, Alexandra Schmiechen, Christopher M Chamberlain, James M Ervasti, Dawn A Lowe. Neopterin/7,8-dihydroneopterin is elevated in Duchenne muscular dystrophy patients and protects mdx skeletal muscle function. Experimental physiology. 2018 07; 103(7):995-1009. doi: 10.1113/ep087031. [PMID: 29791760]
  • Angus Lindsay, Mohd Izani Othman, Hannah Prebble, Sian Davies, Steven P Gieseg. Repetitive cryotherapy attenuates the in vitro and in vivo mononuclear cell activation response. Experimental physiology. 2016 07; 101(7):851-65. doi: 10.1113/ep085795. [PMID: 27094349]
  • A Lindsay, J Healy, W Mills, J Lewis, N Gill, N Draper, S P Gieseg. Impact-induced muscle damage and urinary pterins in professional rugby: 7,8-dihydroneopterin oxidation by myoglobin. Scandinavian journal of medicine & science in sports. 2016 Mar; 26(3):329-37. doi: 10.1111/sms.12436. [PMID: 25772829]
  • A Lindsay, J G Lewis, C Scarrott, N Gill, S P Gieseg, N Draper. Assessing the Effectiveness of Selected Biomarkers in the Acute and Cumulative Physiological Stress Response in Professional Rugby Union through Non-invasive Assessment. International journal of sports medicine. 2015 Jun; 36(6):446-54. doi: 10.1055/s-0034-1398528. [PMID: 25760150]
  • Krasimira Aleksandrova, Shu-Chun Chuang, Heiner Boeing, Hui Zuo, Grethe S Tell, Tobias Pischon, Mazda Jenab, Bas Bueno-de-Mesquita, Stein Emil Vollset, Øivind Midttun, Per Magne Ueland, Veronika Fedirko, Mattias Johansson, Elisabete Weiderpass, Gianluca Severi, Antoine Racine, Marie-Christine Boutron-Ruault, Rudolf Kaaks, Tilman Kühn, Anne Tjønneland, Kim Overvad, J Ramón Quirós, Paula Jakszyn, María-José Sánchez, Miren Dorronsoro, Maria-Dolores Chirlaque, Eva Ardanaz, Kay-Tee Khaw, Nicholas J Wareham, Ruth C Travis, Antonia Trichopoulou, Pagona Lagiou, Dimitrios Trichopoulos, Domenico Palli, Sabina Sieri, Rosario Tumino, Salvatore Panico, Anne M May, Richard Palmqvist, Ingrid Ljuslinder, So Yeon J Kong, Heinz Freisling, Marc J Gunter, Yunxia Lu, Amanda J Cross, Elio Riboli, Paolo Vineis. A prospective study of the immune system activation biomarker neopterin and colorectal cancer risk. Journal of the National Cancer Institute. 2015 Apr; 107(4):. doi: 10.1093/jnci/djv010. [PMID: 25713165]
  • Steven P Gieseg, Zunika Amit, Ya-Ting Yang, Anastasia Shchepetkina, Hanadi Katouah. Oxidant production, oxLDL uptake, and CD36 levels in human monocyte–derived macrophages are downregulated by the macrophage-generated antioxidant 7,8-dihydroneopterin. Antioxidants & redox signaling. 2010 Nov; 13(10):1525-34. doi: 10.1089/ars.2009.3065. [PMID: 20408759]
  • Carole A Firth, Andrew D Laing, Sarah K Baird, Joseph Pearson, Steven P Gieseg. Inflammatory sites as a source of plasma neopterin: measurement of high levels of neopterin and markers of oxidative stress in pus drained from human abscesses. Clinical biochemistry. 2008 Sep; 41(13):1078-83. doi: 10.1016/j.clinbiochem.2008.06.008. [PMID: 18619433]
  • Carole A Firth, Elizabeth M Crone, Elizabeth A Flavall, Justin A Roake, Steven P Gieseg. Macrophage mediated protein hydroperoxide formation and lipid oxidation in low density lipoprotein are inhibited by the inflammation marker 7,8-dihydroneopterin. Biochimica et biophysica acta. 2008 Jun; 1783(6):1095-101. doi: 10.1016/j.bbamcr.2008.02.010. [PMID: 18342632]
  • Elizabeth A Flavall, Elizabeth M Crone, Grant A Moore, Steven P Gieseg. Dissociation of neopterin and 7,8-dihydroneopterin from plasma components before HPLC analysis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Feb; 863(1):167-71. doi: 10.1016/j.jchromb.2007.12.019. [PMID: 18234568]
  • S P Gieseg, E M Crone, E A Flavall, Z Amit. Potential to inhibit growth of atherosclerotic plaque development through modulation of macrophage neopterin/7,8-dihydroneopterin synthesis. British journal of pharmacology. 2008 Feb; 153(4):627-35. doi: 10.1038/sj.bjp.0707408. [PMID: 17700723]
  • Olga Bratslavska, Diana Platace, Edvīns Miklasevics, Dietmar Fuchs, Agris Martinsons. Influence of neopterin and 7,8-dihydroneopterin on the replication of Coxsackie type B5 and influenza A viruses. Medical microbiology and immunology. 2007 Mar; 196(1):23-9. doi: 10.1007/s00430-006-0025-y. [PMID: 16868770]
  • Sarah K Baird, Linzi Reid, Mark B Hampton, Steven P Gieseg. OxLDL induced cell death is inhibited by the macrophage synthesised pterin, 7,8-dihydroneopterin, in U937 cells but not THP-1 cells. Biochimica et biophysica acta. 2005 Sep; 1745(3):361-9. doi: 10.1016/j.bbamcr.2005.07.001. [PMID: 16084608]
  • Steven P Gieseg, Joseph Pearson, Carole A Firth. Protein hydroperoxides are a major product of low density lipoprotein oxidation during copper, peroxyl radical and macrophage-mediated oxidation. Free radical research. 2003 Sep; 37(9):983-91. doi: 10.1080/10715760310001603612. [PMID: 14670006]
  • Steven P Gieseg, Sara Cato. Inhibition of THP-1 cell-mediated low-density lipoprotein oxidation by the macrophage-synthesised pterin, 7,8-dihydroneopterin. Redox report : communications in free radical research. 2003; 8(2):113-5. doi: 10.1179/135100003125001396. [PMID: 12804014]
  • Sean Duggan, Christopher Rait, Aaron Platt, Steven Gieseg. Protein and thiol oxidation in cells exposed to peroxyl radicals is inhibited by the macrophage synthesised pterin 7,8-dihydroneopterin. Biochimica et biophysica acta. 2002 Aug; 1591(1-3):139-145. doi: 10.1016/s0167-4889(02)00272-0. [PMID: 12183064]
  • Inga Herpfer, Joachim Greilberger, Gerhard Ledinski, Bernhard Widner, Dietmar Fuchs, Günther Jürgens. Neopterin and 7,8-dihydroneopterin interfere with low density lipoprotein oxidation mediated by peroxynitrite and/or copper. Free radical research. 2002 May; 36(5):509-20. doi: 10.1080/10715760290025898. [PMID: 12150539]
  • S P Gieseg, J Whybrow, D Glubb, C Rait. Protection of U937 cells from free radical damage by the macrophage synthesized antioxidant 7,8-dihydroneopterin. Free radical research. 2001 Sep; 35(3):311-8. doi: 10.1080/10715760100300841. [PMID: 11697129]
  • S P Gieseg, G Maghzal, D Glubb. Protection of erythrocytes by the macrophage synthesized antioxidant 7,8 dihydroneopterin. Free radical research. 2001 Feb; 34(2):123-36. doi: 10.1080/10715760100300121. [PMID: 11264890]
  • S Duggan, C Rait, J M Gebicki, S P Gieseg. Inhibition of protein oxidation by the macrophage-synthesised antioxidant 7,8-dihydroneopterin. Redox report : communications in free radical research. 2001; 6(3):188-90. doi: 10.1179/135100001101536175. [PMID: 11523596]
  • H Pagel, J Fandrey, W Schobersberger, D Fuchs, W Jelkmann. Effects of neopterin and 7,8-dihydroneopterin on hypoxia-induced renal erythropoietin production. European journal of haematology. 1999 May; 62(5):341-5. doi: 10.1111/j.1600-0609.1999.tb01913.x. [PMID: 10359064]
  • C Murr, L C Fuith, B Widner, B Wirleitner, G Baier-Bitterlich, D Fuchs. Increased neopterin concentrations in patients with cancer: indicator of oxidative stress?. Anticancer research. 1999 May; 19(3A):1721-8. doi: NULL. [PMID: 10470106]
  • S P Gieseg, G Reibnegger, H Wachter, H Esterbauer. 7,8 Dihydroneopterin inhibits low density lipoprotein oxidation in vitro. Evidence that this macrophage secreted pteridine is an anti-oxidant. Free radical research. 1995 Aug; 23(2):123-36. doi: 10.3109/10715769509064027. [PMID: 7581810]
  • G Weiss, D Fuchs, A Hausen, G Reibnegger, E R Werner, G Werner-Felmayer, E Semenitz, M P Dierich, H Wachter. Neopterin modulates toxicity mediated by reactive oxygen and chloride species. FEBS letters. 1993 Apr; 321(1):89-92. doi: 10.1016/0014-5793(93)80627-7. [PMID: 8385632]
  • D Fuchs, S Milstien, A Krämer, G Reibnegger, E R Werner, J J Goedert, S Kaufman, H Wachter. Urinary neopterin concentrations vs total neopterins for clinical utility. Clinical chemistry. 1989 Dec; 35(12):2305-7. doi: . [PMID: 2591046]
  • E R Werner, D Fuchs, A Hausen, G Reibnegger, H Wachter. Simultaneous determination of neopterin and creatinine in serum with solid-phase extraction and on-line elution liquid chromatography. Clinical chemistry. 1987 Nov; 33(11):2028-33. doi: . [PMID: 3119253]
  • J L Dhondt, J P Farriaux, A Boudha, C Largillière, J Ringel, M M Roger, R J Leeming. Neonatal hyperphenylalaninemia presumably caused by guanosine triphosphate-cyclohydrolase deficiency. The Journal of pediatrics. 1985 Jun; 106(6):954-6. doi: 10.1016/s0022-3476(85)80251-1. [PMID: 3873535]