Tetrahydrofolic acid (BioDeep_00000004381)

Main id: BioDeep_00000229169

 

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Chemicals and Drugs natural product BioNovoGene_Lab2019


代谢物信息卡片


2-{[4-({[(6S)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid

化学式: C19H23N7O6 (445.1709738)
中文名称: 四氢叶酸, 四氢叶酸, 四氢叶酸, 四氢叶酸
谱图信息: 最多检出来源 Homo sapiens(feces) 50%

分子结构信息

SMILES: C1C(NC2=C(N1)N=C(NC2=O)N)CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
InChI: InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)

描述信息

Tetrahydrofolate is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593). Folate is important for cells and tissues that rapidly divide. Cancer cells divide rapidly, and drugs that interfere with folate metabolism are used to treat cancer. Methotrexate is a drug often used to treat cancer because it inhibits the production of the active form, tetrahydrofolate. Unfortunately, methotrexate can be toxic, producing side effects such as inflammation in the digestive tract that make it difficult to eat normally. -- Wikipedia; Signs of folic acid deficiency are often subtle. Diarrhea, loss of appetite, and weight loss can occur. Additional signs are weakness, sore tongue, headaches, heart palpitations, irritability, and behavioral disorders. Women with folate deficiency who become pregnant are more likely to give birth to low birth weight and premature infants, and infants with neural tube defects. In adults, anemia is a sign of advanced folate deficiency. In infants and children, folate deficiency can slow growth rate. Some of these symptoms can also result from a variety of medical conditions other than folate deficiency. It is important to have a physician evaluate these symptoms so that appropriate medical care can be given. -- Wikipedia; Folinic acid is a form of folate that can help rescue or reverse the toxic effects of methotrexate. Folinic acid is not the same as folic acid. Folic acid supplements have little established role in cancer chemotherapy. There have been cases of severe adverse effects of accidental substitution of folic acid for folinic acid in patients receiving methotrexate cancer chemotherapy. It is important for anyone receiving methotrexate to follow medical advice on the use of folic or folinic acid supplements. -- Wikipedia. Low concentrations of folate, vitamin B12, or vitamin B6 may increase the level of homocysteine, an amino acid normally found in blood. There is evidence that an elevated homocysteine level is an independent risk factor for heart disease and stroke. The evidence suggests that high levels of homocysteine may damage coronary arteries or make it easier for blood clotting cells called platelets to clump together and form a clot. However, there is currently no evidence available to suggest that lowering homocysteine with vitamins will reduce your risk of heart disease. Clinical intervention trials are needed to determine whether supplementation with folic acid, vitamin B12 or vitamin B6 can lower your risk of developing coronary heart disease. -- Wikipedia.
Tetrahydrofolate is a soluble coenzyme (vitamin B9) that is synthesized de novo by plants and microorganisms, and absorbed from the diet by animals. It is composed of three distinct parts: a pterin ring, a p-ABA (p-aminobenzoic acid) and a polyglutamate chain with a number of residues varying between 1 and 8. Only the tetra-reduced form of the molecule serves as a coenzyme for C1 transfer reactions. In biological systems, the C1-units exist under various oxidation states and the different tetrahydrofolate derivatives constitute a family of related molecules named indistinctly under the generic term folate. (PMID 16042593)

同义名列表

14 个代谢物同义名

2-{[4-({[(6S)-4-hydroxy-2-imino-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid; 2-{[4-({[(6S)-4-hydroxy-2-imino-1,2,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid; Tetrahydropteroyl mono-L-glutamate; L-5,6,7,8-Tetrahydrofolic acid; (6S)-5,6,7,8-Tetrahydrofolate; 5,6,7,8-Tetrahydrofolic acid; Tetrahydropteroylglutamate; (6S)-Tetrahydrofolic acid; 5,6,7,8-Tetrahydrofolate; (6S)-Tetrahydrofolate; tetrahydrofolic acid; Tetrahydrafolate; Tetrahydrofolate; Tetra-H-folate



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(9)

BioCyc(15)

PlantCyc(0)

代谢反应

1044 个相关的代谢反应过程信息。

Reactome(151)

BioCyc(24)

WikiPathways(0)

Plant Reactome(861)

INOH(8)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

7 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

  • Minmin Zhang, Guangfeng Liu, Yunlong Zhang, Ting Chen, Shanshan Feng, Rujie Cai, Changrui Lu. The Second Class of Tetrahydrofolate (THF-II) Riboswitches Recognizes the Tetrahydrofolic Acid Ligand via Local Conformation Changes. International journal of molecular sciences. 2022 May; 23(11):. doi: 10.3390/ijms23115903. [PMID: 35682583]
  • Naveen Kr Dubey. Sensitive and rapid simultaneous quantitation of leucovorin and its major active metabolite 5-methyl-tetrahydrofolate in human plasma using a liquid chromatography coupled with triple quadruple mass spectrometry. Biomedical chromatography : BMC. 2022 Apr; 36(4):e5299. doi: 10.1002/bmc.5299. [PMID: 34913177]
  • Shaimaa M Sallam, Eman Shawky, Samah M El Sohafy. Determination of the effect of germination on the folate content of the seeds of some legumes using HPTLC-mass spectrometry-multivariate image analysis. Food chemistry. 2021 Nov; 362(?):130206. doi: 10.1016/j.foodchem.2021.130206. [PMID: 34082289]
  • Natalia I Krupenko, Jaspreet Sharma, Peter Pediaditakis, Kristi L Helke, Madeline S Hall, Xiuxia Du, Susan Sumner, Sergey A Krupenko. Aldh1l2 knockout mouse metabolomics links the loss of the mitochondrial folate enzyme to deregulation of a lipid metabolism observed in rare human disorder. Human genomics. 2020 11; 14(1):41. doi: 10.1186/s40246-020-00291-3. [PMID: 33168096]
  • Weimin Wang, Haibo Wang, Liangliang Xiang, Tengyang Ni, Feng Jin, Jianliang Deng, Yunlei Zhang, Ishikawa Shintaro, Yan Zhou, Yanqing Liu. DJ‑1 is a new prognostic marker and predicts chemotherapy efficacy in colorectal cancer. Oncology reports. 2020 07; 44(1):77-90. doi: 10.3892/or.2020.7593. [PMID: 32627002]
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  • David A Korasick, Pramod K Kandoth, John J Tanner, Melissa G Mitchum, Lesa J Beamer. Impaired folate binding of serine hydroxymethyltransferase 8 from soybean underlies resistance to the soybean cyst nematode. The Journal of biological chemistry. 2020 03; 295(11):3708-3718. doi: 10.1074/jbc.ra119.012256. [PMID: 32014996]
  • Petra Ložnjak, Carolina García-Salinas, Rocío Isabel Díaz de la Garza, Anette Bysted, Jette Jakobsen. The use of a plant enzyme for rapid and sensitive analysis of naturally-occurring folates in food by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2019 Jun; 1594(?):34-44. doi: 10.1016/j.chroma.2019.02.037. [PMID: 30799066]
  • Wenzhu Guo, Tong Lian, Baobao Wang, Jiantao Guan, Dong Yuan, Huan Wang, Fardous Mohammad Safiul Azam, Xing Wan, Weixuan Wang, Qiuju Liang, Haiyang Wang, Jinxing Tu, Chunyi Zhang, Ling Jiang. Genetic mapping of folate QTLs using a segregated population in maize. Journal of integrative plant biology. 2019 Jun; 61(6):675-690. doi: 10.1111/jipb.12811. [PMID: 30938052]
  • Judy R Rees, Carolyn B Morris, Janet L Peacock, Per M Ueland, Elizabeth L Barry, Gail E McKeown-Eyssen, Jane C Figueiredo, Dale C Snover, John A Baron. Unmetabolized Folic Acid, Tetrahydrofolate, and Colorectal Adenoma Risk. Cancer prevention research (Philadelphia, Pa.). 2017 Aug; 10(8):451-458. doi: 10.1158/1940-6207.capr-16-0278. [PMID: 28600398]
  • Noelia Foresi, Martín L Mayta, Anabella F Lodeyro, Denise Scuffi, Natalia Correa-Aragunde, Carlos García-Mata, Claudia Casalongué, Néstor Carrillo, Lorenzo Lamattina. Expression of the tetrahydrofolate-dependent nitric oxide synthase from the green alga Ostreococcus tauri increases tolerance to abiotic stresses and influences stomatal development in Arabidopsis. The Plant journal : for cell and molecular biology. 2015 Jun; 82(5):806-21. doi: 10.1111/tpj.12852. [PMID: 25880454]
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  • Rima Obeid, Susanne H Kirsch, Mariz Kasoha, Rudolf Eckert, Wolfgang Herrmann. Concentrations of unmetabolized folic acid and primary folate forms in plasma after folic acid treatment in older adults. Metabolism: clinical and experimental. 2011 May; 60(5):673-80. doi: 10.1016/j.metabol.2010.06.020. [PMID: 20727555]
  • Avinash C Srivastava, Perla A Ramos-Parra, Mohamed Bedair, Ana L Robledo-Hernández, Yuhong Tang, Lloyd W Sumner, Rocío I Díaz de la Garza, Elison B Blancaflor. The folylpolyglutamate synthetase plastidial isoform is required for postembryonic root development in Arabidopsis. Plant physiology. 2011 Mar; 155(3):1237-51. doi: 10.1104/pp.110.168278. [PMID: 21233333]
  • Hiroki Matsui, Saori Yoneda, Tomomi Ban-Tokuda, Masaaki Wakita. Diversity of the formyltetrahydrofolate synthetase (FTHFS) gene in the proximal and mid ostrich colon. Current microbiology. 2011 Jan; 62(1):1-6. doi: 10.1007/s00284-010-9661-y. [PMID: 20458481]
  • Carolyn M Summers, Laura E Mitchell, Anna Stanislawska-Sachadyn, Shirley F Baido, Ian A Blair, Joan M Von Feldt, Alexander S Whitehead. Genetic and lifestyle variables associated with homocysteine concentrations and the distribution of folate derivatives in healthy premenopausal women. Birth defects research. Part A, Clinical and molecular teratology. 2010 Aug; 88(8):679-88. doi: 10.1002/bdra.20683. [PMID: 20544798]
  • Cullen K T Pang, Joshua H Hunter, Ramesh Gujjar, Ramulu Podutoori, Julie Bowman, Devaraja G Mudeppa, Pradipsinh K Rathod. Catalytic and ligand-binding characteristics of Plasmodium falciparum serine hydroxymethyltransferase. Molecular and biochemical parasitology. 2009 Nov; 168(1):74-83. doi: 10.1016/j.molbiopara.2009.06.011. [PMID: 19591883]
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  • Valérie de Crécy-Lagard, Basma El Yacoubi, Rocío Díaz de la Garza, Alexandre Noiriel, Andrew D Hanson. Comparative genomics of bacterial and plant folate synthesis and salvage: predictions and validations. BMC genomics. 2007 Jul; 8(?):245. doi: 10.1186/1471-2164-8-245. [PMID: 17645794]
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