Isoxanthopterin (BioDeep_00000001360)

 

Secondary id: BioDeep_00000405874

human metabolite Endogenous


代谢物信息卡片


2-amino-1,4,7,8-tetrahydropteridine-4,7-dione

化学式: C6H5N5O2 (179.04432300000002)
中文名称: 异黄蝶呤
谱图信息: 最多检出来源 Homo sapiens(blood) 1.14%

分子结构信息

SMILES: C1=NC2=C(NC1=O)N=C(NC2=O)N
InChI: InChI=1S/C6H5N5O2/c7-6-10-4-3(5(13)11-6)8-1-2(12)9-4/h1H,(H4,7,9,10,11,12,13)

描述信息

Isoxanthopterin is a pteridine normally present in plasma, urine, and other bodily fluids also vary from normal concentrations in some disease states and also have diagnostic value. Pteridines urinary concentrations seem to vary independently from each other and from normal values to yield a pattern of excreted pteridines that is diagnostic for different species, tissues, and tumor types. Intravenous or intramuscular administration of isoxanthopterin inhibits the growth rates of animal tumor models. ; Pteridin derivatives are a family of organic compound with very similar chemical structures which play an important biochemistry role. Pteridines metabolism and its regulation in normal and pathological conditions have not been extensively investigated due to the difficulty of their quantification. A significant decrease of isoxanthopterin has been determined in cancer patients. (PMID 15837549, 9800651); Xanthine dehydrogenase (XDH) is the enzymes responsible for the conversion of xanthine to uric acid. It requires the presence of the molybdenum cofactor for its proper functioning. XDH is reported to have additional functions, i.e., the conversion of pterin to isoxanthopterin, one of the steps the degradation pathway of 5,6,7,8-tetrahydrobiopterin (BH4). Isoxanthopterin is very low in some cases of hereditary xanthinuria (OMIM 278300) and molybdenum cofactor deficiency (OMIM 252150). (PMID: 8812740). Isoxanthopterin is found in soy bean.
Isoxanthopterin is a pteridine normally present in plasma, urine, and other bodily fluids also vary from normal concentrations in some disease states and also have diagnostic value. Pteridines urinary concentrations seem to vary independently from each other and from normal values to yield a pattern of excreted pteridines that is diagnostic for different species, tissues, and tumor types. Intravenous or intramuscular administration of isoxanthopterin inhibits the growth rates of animal tumor models. Pteridin derivatives are a family of organic compound with very similar chemical structures which play an important biochemistry role. Pteridines metabolism and its regulation in normal and pathological conditions have not been extensively investigated due to the difficulty of their quantification. A significant decrease of isoxanthopterin has been determined in cancer patients. (PMID 15837549, 9800651). Xanthine dehydrogenase (XDH) is the enzymes responsible for the conversion of xanthine to uric acid. It requires the presence of the molybdenum cofactor for its proper functioning. XDH is reported to have additional functions, i.e., the conversion of pterin to isoxanthopterin, one of the steps the degradation pathway of 5,6,7,8-tetrahydrobiopterin (BH4). Isoxanthopterin is very low in some cases of hereditary xanthinuria (OMIM 278300) and molybdenum cofactor deficiency (OMIM 252150). (PMID: 8812740).
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同义名列表

6 个代谢物同义名

2-amino-1,4,7,8-tetrahydropteridine-4,7-dione; 2-amino-1,8-dihydropteridine-4,7-dione; 2-Amino-3H,8H-pteridine-4,7-dione; 2-Amino-4,7-dihydroxypteridine; 2-Aminopteridine-4,7-diol; Isoxanthopterin



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

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PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 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

  • Pei-Zhong Bao, Jun Ye, Lian-Shu Han, Wen-Juan Qiu, Hui-Wen Zhang, Yong-Guo Yu, Jian-Guo Wang, Xue-Fan Gu. Application of isoxanthopterin as a new pterin marker in the differential diagnosis of hyperphenylalaninemia. World journal of pediatrics : WJP. 2019 Feb; 15(1):66-71. doi: 10.1007/s12519-018-0202-2. [PMID: 30443829]
  • Angus Lindsay, Preston M McCourt, Peter Karachunski, Dawn A Lowe, James M Ervasti. Xanthine oxidase is hyper-active in Duchenne muscular dystrophy. Free radical biology & medicine. 2018 12; 129(?):364-371. doi: 10.1016/j.freeradbiomed.2018.10.404. [PMID: 30312761]
  • Lingling Huang, Lan Guo, Yiqun Wan, Pingping Pan, Lei Feng. Simultaneous determination of three potential cancer biomarkers in rat urine by synchronous fluorescence spectroscopy. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2014; 120(?):595-601. doi: 10.1016/j.saa.2013.12.001. [PMID: 24365397]
  • Gabriella Allegri, Heleno José Bezerra Costa Netto, Luiz Nelson Lopes Ferreira Gomes, Maria Lúcia Costa de Oliveira, Fernanda Bertão Scalco, Francisco Radler de Aquino Neto. Determination of six pterins in urine by LC-MS/MS. Bioanalysis. 2012 Jul; 4(14):1739-46. doi: 10.4155/bio.12.131. [PMID: 22877220]
  • M J Culzoni, A Mancha de Llanos, M M De Zan, A Espinosa-Mansilla, F Cañada-Cañada, A Muñoz de la Peña, H C Goicoechea. Enhanced MCR-ALS modeling of HPLC with fast scan fluorimetric detection second-order data for quantitation of metabolic disorder marker pteridines in urine. Talanta. 2011 Oct; 85(5):2368-74. doi: 10.1016/j.talanta.2011.07.086. [PMID: 21962655]
  • Megan S Plank, Teleka C Calderon, Yayesh Asmerom, Danilo S Boskovic, Danilyn M Angeles. Biochemical measurement of neonatal hypoxia. Journal of visualized experiments : JoVE. 2011 Aug; ?(54):. doi: 10.3791/2948. [PMID: 21897351]
  • A Mancha de Llanos, M M De Zan, M J Culzoni, A Espinosa-Mansilla, F Cañada-Cañada, A Muñoz de la Peña, H C Goicoechea. Determination of marker pteridines in urine by HPLC with fluorimetric detection and second-order multivariate calibration using MCR-ALS. Analytical and bioanalytical chemistry. 2011 Feb; 399(6):2123-35. doi: 10.1007/s00216-010-4071-3. [PMID: 20711774]
  • Sanjeewa Gamagedara, Stephen Gibbons, Yinfa Ma. Investigation of urinary pteridine levels as potential biomarkers for noninvasive diagnosis of cancer. Clinica chimica acta; international journal of clinical chemistry. 2011 Jan; 412(1-2):120-8. doi: 10.1016/j.cca.2010.09.015. [PMID: 20869359]
  • Yi-Qun Wan, Li-Juan Tang, Ting Tan. Simultaneous determination of xanthopterin and isoxanthopterin in human urine by synchronous fluorescence spectroscopy. Journal of fluorescence. 2010 Nov; 20(6):1191-8. doi: 10.1007/s10895-010-0667-4. [PMID: 20419340]
  • Lei Feng, Aiping Yan, Lin Chen, Yiqun Wan. [Determination of isoxanthopterin in human urine by solid phase extraction-high performance anion-exchange chromatography coupled with integrated pulsed amperometric detection]. Se pu = Chinese journal of chromatography. 2010 Apr; 28(4):408-12. doi: 10.3724/sp.j.1123.2010.00408. [PMID: 20712126]
  • Jan Trnka, Frances H Blaikie, Angela Logan, Robin A J Smith, Michael P Murphy. Antioxidant properties of MitoTEMPOL and its hydroxylamine. Free radical research. 2009 Jan; 43(1):4-12. doi: 10.1080/10715760802582183. [PMID: 19058062]
  • Susana Granell, Oriol Bulbena, Meritxell Genesca, Luis Sabater, Juan Sastre, Emilio Gelpi, Daniel Closa. Mobilization of xanthine oxidase from the gastrointestinal tract in acute pancreatitis. BMC gastroenterology. 2004 Jan; 4(?):1. doi: 10.1186/1471-230x-4-1. [PMID: 14728722]
  • R Walter, N Blau, A Schaffner, M Schneemann, R Speich, R Stocker, B Naujeck, G Schoedon. Inhalation of the nitric oxide synthase cofactor tetrahydrobiopterin in healthy volunteers. American journal of respiratory and critical care medicine. 1997 Dec; 156(6):2006-10. doi: 10.1164/ajrccm.156.6.96-12084. [PMID: 9412588]
  • N Blau, J B de Klerk, B Thöny, C W Heizmann, L Kierat, J A Smeitink, M Duran. Tetrahydrobiopterin loading test in xanthine dehydrogenase and molybdenum cofactor deficiencies. Biochemical and molecular medicine. 1996 Aug; 58(2):199-203. doi: 10.1006/bmme.1996.0049. [PMID: 8812740]
  • T Yamamoto, Y Moriwaki, S Takahashi, Z Tsutsumi, J Yamakita, Y Nasako, K Hiroishi, K Higashino. Determination of human plasma xanthine oxidase activity by high-performance liquid chromatography. Journal of chromatography. B, Biomedical applications. 1996 Jun; 681(2):395-400. doi: 10.1016/0378-4347(96)00071-0. [PMID: 8811453]
  • M Goldberg, H Eichinger, W Otten, M Merkenschlager. [Pteridine pattern in the urine of swine of different breeds and halothane genotypes in relation to nutrition and stress]. Tierarztliche Praxis. 1991 Oct; 19(5):493-6. doi: NULL. [PMID: 1759264]
  • T Sasaoka, N Kaneda, T Nagatsu. Highly sensitive assay for xanthine oxidase activity by high-performance liquid chromatography with fluorescence detection. Journal of chromatography. 1988 Feb; 424(2):392-7. doi: 10.1016/s0378-4347(00)81118-4. [PMID: 3372632]
  • J H Woolf, C A Nichol, D S Duch. Determination of biopterin and other pterins in tissues and body fluids by high-performance liquid chromatography. Journal of chromatography. 1983 May; 274(?):398-402. doi: 10.1016/s0378-4347(00)84451-5. [PMID: 6874847]
  • B Stea, R M Halpern, B C Halpern, R A Smith. Urinary excretion levels of unconjugated pterins in cancer patients and normal individuals. Clinica chimica acta; international journal of clinical chemistry. 1981 Jul; 113(3):231-42. doi: 10.1016/0009-8981(81)90277-1. [PMID: 7261396]
  • J A BLAIR. Isolation of isoxanthopterin from human urine. The Biochemical journal. 1958 Mar; 68(3):385-7. doi: 10.1042/bj0680385a. [PMID: 13522634]