5,10-Methylene-THF (BioDeep_00000004386)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


2-({4-[(6aR)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H,8H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid

化学式: C20H23N7O6 (457.1709738)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.8%

分子结构信息

SMILES: c12[nH]c(nc(=O)c1N1[C@H](CN2)CN(C1)c1ccc(cc1)C(=O)N[C@@H](CCC(=O)O)C(=O)O)N
InChI: InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)

描述信息

5,10-Methylene-THF is an intermediate in glycine, serine and threonine metabolism and one carbon metabolism. 5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase. 5,10-Methylene-THF is a substrate for Methylenetetrahydrofolate reductase. This enzyme converts 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate. This reaction is required for the multistep process that converts the amino acid homocysteine to methionine. The body uses methionine to make proteins and other important compounds. 5,10-CH2-THF is a substrate for many enzymes including Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), Aminomethyltransferase (mitochondrial), Serine hydroxymethyltransferase (mitochondrial), Methylenetetrahydrofolate reductase, C-1-tetrahydrofolate synthase (cytoplasmic), Serine hydroxymethyltransferase (cytosolic) and Thymidylate synthase.
5,10-Methylene-THF is an intermediate in the metabolism of Methane and the metabolism of Nitrogen. It is a substrate for Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), Aminomethyltransferase (mitochondrial), Serine hydroxymethyltransferase (mitochondrial), Methylenetetrahydrofolate reductase, C-1-tetrahydrofolate synthase (cytoplasmic), Serine hydroxymethyltransferase (cytosolic) and Thymidylate synthase. [HMDB]
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同义名列表

18 个代谢物同义名

2-({4-[(6aR)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H,8H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid; 2-({4-[(6aR)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid; 2-[[4-[(6aR)-3-amino-1-oxo-4,5,6,6a,7,9-hexahydroimidazo[1,5-f]pteridin-8-yl]benzoyl]amino]pentanedioic acid; 5,10-Methylenetetrahydrofolate monohydrochloride, (L-glu)-isomer; 5,10-Methylenetetrahydrofolate, (L-glu)-(S)-isomer; 5,10-Methylenetetrahydrofolate, (D-glu)-isomer; (6R)-5,10-Methylenetetrahydrofolic acid; 5,10-Methenyltetrahydropteroylglutamate; 5,10-Methylene-5,6,7,8-tetrahydrofolate; (6R)-5,10-Methylenetetrahydrofolate; 5,10-Methylenetetrahydrofolic acid; N5>,N10-methylenetetrahydrofolate; 5,10-Methylene-6-hydrofolic acid; 5,10-Methylenetetrahydrofolate; 5,10-Methylene-6-hydrofolate; Tetrahydromethylenefolate; 5,10-methylene-THF; CH2H4Folate



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(9)

PlantCyc(0)

代谢反应

144 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(16)

WikiPathways(6)

Plant Reactome(0)

INOH(6)

PlantCyc(13)

COVID-19 Disease Map(1)

PathBank(102)

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

  • Armelle Vigouroux, Thibault Meyer, Anaïs Naretto, Pierre Legrand, Magali Aumont-Nicaise, Aurélie Di Cicco, Sébastien Renoud, Jeanne Doré, Daniel Lévy, Ludovic Vial, Céline Lavire, Solange Moréra. Characterization of the first tetrameric transcription factor of the GntR superfamily with allosteric regulation from the bacterial pathogen Agrobacterium fabrum. Nucleic acids research. 2021 01; 49(1):529-546. doi: 10.1093/nar/gkaa1181. [PMID: 33313837]
  • Helena Taflin, Elisabeth Odin, Göran Carlsson, Roger Tell, Bengt Gustavsson, Yvonne Wettergren. Plasma deoxyuridine as a surrogate marker for toxicity and early clinical response in patients with metastatic colorectal cancer after 5-FU-based therapy in combination with arfolitixorin. Cancer chemotherapy and pharmacology. 2021 01; 87(1):31-41. doi: 10.1007/s00280-020-04173-2. [PMID: 33099678]
  • Aamod S Dekhne, Changwen Ning, Md Junayed Nayeen, Khushbu Shah, Hasini Kalpage, Josephine Frühauf, Adrianne Wallace-Povirk, Carrie O'Connor, Zhanjun Hou, Seongho Kim, Maik Hüttemann, Aleem Gangjee, Larry H Matherly. Cellular Pharmacodynamics of a Novel Pyrrolo[3,2-d]pyrimidine Inhibitor Targeting Mitochondrial and Cytosolic One-Carbon Metabolism. Molecular pharmacology. 2020 01; 97(1):9-22. doi: 10.1124/mol.119.117937. [PMID: 31707355]
  • Mehmet Serdar Kutuk, Asli Subasioglu, Semih Uludag, Nazife Tascioglu, Mahmut Tuncay Ozgun, Munis Dundar. The effect of parental 5,10-methylenetetrahydrofolate reductase 677C/T and 1298A/C gene polymorphisms on response to single-dose methotrexate in tubal ectopic pregnancy. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians. 2017 May; 30(10):1232-1237. doi: 10.1080/14767058.2016.1209652. [PMID: 27379466]
  • Natario L Couser, Julie McClure, Michael W Evans, Nathan R Haines, Susan K Burden, Joseph Muenzer. Homocysteinemia due to MTHFR deficiency in a young adult presenting with bilateral lens subluxations. Ophthalmic genetics. 2017 Jan; 38(1):91-94. doi: 10.3109/13816810.2016.1143017. [PMID: 27046515]
  • Martin Groth, Guillaume Moissiard, Markus Wirtz, Haifeng Wang, Carolina Garcia-Salinas, Perla A Ramos-Parra, Sylvain Bischof, Suhua Feng, Shawn J Cokus, Amala John, Danielle C Smith, Jixian Zhai, Christopher J Hale, Jeff A Long, Ruediger Hell, Rocío I Díaz de la Garza, Steven E Jacobsen. MTHFD1 controls DNA methylation in Arabidopsis. Nature communications. 2016 06; 7(?):11640. doi: 10.1038/ncomms11640. [PMID: 27291711]
  • José F Cascalheira, Mónica Gonçalves, Madalena Barroso, Rita Castro, Manuela Palmeira, André Serpa, Ana C Dias-Cabral, Fernanda C Domingues, Sofia Almeida. Association of the transcobalamin II gene 776C → G polymorphism with Alzheimer's type dementia: dependence on the 5, 10-methylenetetrahydrofolate reductase 1298A → C polymorphism genotype. Annals of clinical biochemistry. 2015 Jul; 52(Pt 4):448-55. doi: 10.1177/0004563214561770. [PMID: 25395544]
  • Yvonne Wettergren, Helena Taflin, Elisabeth Odin, Karl Kodeda, Kristoffer Derwinger. A pharmacokinetic and pharmacodynamic investigation of Modufolin® compared to Isovorin® after single dose intravenous administration to patients with colon cancer: a randomized study. Cancer chemotherapy and pharmacology. 2015 Jan; 75(1):37-47. doi: 10.1007/s00280-014-2611-9. [PMID: 25342290]
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  • Andrew H Ford, Leon Flicker, Helman Alfonso, Graeme J Hankey, Paul E Norman, Frank M van Bockxmeer, Osvaldo P Almeida. Plasma homocysteine and MTHFRC677T polymorphism as risk factors for incident dementia. Journal of neurology, neurosurgery, and psychiatry. 2012 Jan; 83(1):70-5. doi: 10.1136/jnnp.2011.242446. [PMID: 21746742]
  • Jian-Yuan Zhao, Jing-Wei Sun, Zhuo-Ya Gu, Jue Wang, Er-Li Wang, Xue-Yan Yang, Bin Qiao, Wen-Yuan Duan, Guo-Ying Huang, Hong-Yan Wang. Genetic polymorphisms of the TYMS gene are not associated with congenital cardiac septal defects in a Han Chinese population. PloS one. 2012; 7(2):e31644. doi: 10.1371/journal.pone.0031644. [PMID: 22384047]
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  • Michael Kube, Jelena Mitrovic, Bojan Duduk, Ralf Rabus, Erich Seemüller. Current view on phytoplasma genomes and encoded metabolism. TheScientificWorldJournal. 2012; 2012(?):185942. doi: 10.1100/2012/185942. [PMID: 22550465]
  • Ganesh Chauhan, Ismeet Kaur, Rubina Tabassum, Om Prakash Dwivedi, Saurabh Ghosh, Nikhil Tandon, Dwaipayan Bharadwaj. Common variants of homocysteine metabolism pathway genes and risk of type 2 diabetes and related traits in Indians. Experimental diabetes research. 2012; 2012(?):960318. doi: 10.1155/2012/960318. [PMID: 21960995]
  • Emel Ergul, Ali Sazci, Ihsan Kara. Methylenetetrahydrofolate reductase gene polymorphisms in Turkish children with attention-deficit/hyperactivity disorder. Genetic testing and molecular biomarkers. 2012 Jan; 16(1):67-9. doi: 10.1089/gtmb.2011.0062. [PMID: 21819229]
  • Asma Ezzaher, Dhouha Haj Mouhamed, Anwar Mechri, Asma Omezzine, Fadoua Neffati, Wahiba Douki, Ali Bouslama, Lotfi Gaha, Mohamed Fadhel Najjar. Hyperhomocysteinemia in Tunisian bipolar I patients. Psychiatry and clinical neurosciences. 2011 Dec; 65(7):664-71. doi: 10.1111/j.1440-1819.2011.02284.x. [PMID: 22176285]
  • Haruka Murakami, Motoyuki Iemitsu, Kiyoshi Sanada, Yuko Gando, Yumi Ohmori, Ryoko Kawakami, Satoshi Sasaki, Izumi Tabata, Motohiko Miyachi. Associations among objectively measured physical activity, fasting plasma homocysteine concentration, and MTHFR C677T genotype. European journal of applied physiology. 2011 Dec; 111(12):2997-3005. doi: 10.1007/s00421-011-1926-z. [PMID: 21451940]
  • Asuri N Prasad, Charles A Rupar, Chitra Prasad. Methylenetetrahydrofolate reductase (MTHFR) deficiency and infantile epilepsy. Brain & development. 2011 Oct; 33(9):758-69. doi: 10.1016/j.braindev.2011.05.014. [PMID: 21778025]
  • Erika R F Siqueira, Cláudia P M S Oliveira, Maria T C Muniz, Filipe Silva, Leila M M B Pereira, Flair J Carrilho. Methylenetetrahydrofolate reductase (MTHFR) C677T polymorphism and high plasma homocysteine in chronic hepatitis C (CHC) infected patients from the Northeast of Brazil. Nutrition journal. 2011 Aug; 10(?):86. doi: 10.1186/1475-2891-10-86. [PMID: 21854603]
  • Kyung Lim Yoon, Jin Hee Ko, Kye Shik Shim, Mi Young Han, Sung Ho Cha, Su Kang Kim, Joo Ho Jung. Polymorphisms of methylenetetrahydrofolate reductase are not a risk factor for Kawasaki disease in the Korean population. Korean journal of pediatrics. 2011 Aug; 54(8):335-9. doi: 10.3345/kjp.2011.54.8.335. [PMID: 22087200]
  • Roman Pavlik, Stephanie Hecht, Robert Ochsenkühn, Ulrich Noss, Peter Lohse, Christian J Thaler. Divergent effects of the 677C>T mutation of the 5,10-methylenetetrahydrofolate reductase (MTHFR) gene on ovarian responsiveness and anti-Müllerian hormone concentrations. Fertility and sterility. 2011 Jun; 95(7):2257-62. doi: 10.1016/j.fertnstert.2011.03.023. [PMID: 21481373]
  • Veronica E Ohrvik, Cornelia M Witthoft. Human folate bioavailability. Nutrients. 2011 04; 3(4):475-90. doi: 10.3390/nu3040475. [PMID: 22254106]
  • So-Young Lee, Hoe-Young Kim, Kyung Mi Park, Stephen Yon Gu Lee, Seong Geun Hong, Hyung-Jong Kim, Dong Ho Yang. MTHFR C677T polymorphism as a risk factor for vascular calcification in chronic hemodialysis patients. Journal of Korean medical science. 2011 Mar; 26(3):461-5. doi: 10.3346/jkms.2011.26.3.461. [PMID: 21394321]
  • Audrey Y Jung, Yvo Smulders, Petra Verhoef, Frans J Kok, Henk Blom, Robert M Kok, Ellen Kampman, Jane Durga. No effect of folic acid supplementation on global DNA methylation in men and women with moderately elevated homocysteine. PloS one. 2011; 6(9):e24976. doi: 10.1371/journal.pone.0024976. [PMID: 21966393]
  • Beata Sarecka-Hujar, Iwona Zak. [Role of the polymorphisms within genes encoding proteins related to endothelial dysfunction in coronary artery disease]. Wiadomosci lekarskie (Warsaw, Poland : 1960). 2011; 64(4):294-300. doi: . [PMID: 22533155]
  • Hui-Qi Low, Christopher P L H Chen, Katherine Kasiman, Anbupalam Thalamuthu, Seok-Shin Ng, Jia-Nee Foo, Hui-Meng Chang, Meng-Cheong Wong, E-Shyong Tai, Jianjun Liu. A comprehensive association analysis of homocysteine metabolic pathway genes in Singaporean Chinese with ischemic stroke. PloS one. 2011; 6(9):e24757. doi: 10.1371/journal.pone.0024757. [PMID: 21935458]
  • Shih-Jen Tsai, Chen-Jee Hong, Heng-Liang Yeh, Ying-Jay Liou, Albert C Yang, Mu-En Liu, Jen-Ping Hwang. Heterozygote advantage of the MTHFR C677T polymorphism on specific cognitive performance in elderly Chinese males without dementia. Dementia and geriatric cognitive disorders. 2011; 32(3):159-63. doi: 10.1159/000333074. [PMID: 21997345]
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  • Tomasz Wlodarski, Jan Kutner, Joanna Towpik, Lukasz Knizewski, Leszek Rychlewski, Andrzej Kudlicki, Maga Rowicka, Andrzej Dziembowski, Krzysztof Ginalski. Comprehensive structural and substrate specificity classification of the Saccharomyces cerevisiae methyltransferome. PloS one. 2011; 6(8):e23168. doi: 10.1371/journal.pone.0023168. [PMID: 21858014]
  • Linda M Liao, Paul Brennan, Dana M van Bemmel, David Zaridze, Vsevolod Matveev, Vladimir Janout, Hellena Kollarova, Vladimir Bencko, Marie Navratilova, Neonila Szeszenia-Dabrowska, Dana Mates, Nathaniel Rothman, Paolo Boffetta, Wong-Ho Chow, Lee E Moore. LINE-1 methylation levels in leukocyte DNA and risk of renal cell cancer. PloS one. 2011; 6(11):e27361. doi: 10.1371/journal.pone.0027361. [PMID: 22076155]
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