5,10-Methenyltetrahydrofolic acid (BioDeep_00000019503)
Main id: BioDeep_00000004430
human metabolite Endogenous Chemicals and Drugs
代谢物信息卡片
化学式: C20H21N7O6 (455.1553)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1C2CN(C=[N+]2C3=C(N1)N=C(NC3=O)N)C4=CC=C(C=C4)C(=O)NC(CCC(=O)O)C(=O)[O-]
InChI: InChI=1S/C20H21N7O6/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/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1
描述信息
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. 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. Low concentrations of folate, vitamin B12, or vitamin B6 may increase your level of homocysteine, an amino acid normally found in your 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. Methylene tetrahydrofolate (CH2FH4) is formed from tetrahydrofolate by the addition of methylene groups from one of three carbon donors: formaldehyde, serine, or glycine. Methyl tetrahydrofolate(CH3FH4) can be made from methylene tetrahydrofolate by reduction of the methylene group, and formyl tetrahydrofolate (CHOFH4, folinic acid) is made by oxidation of methylene tetrahydrofolate. In the form of a series of tetrahydrofolate compounds, folate derivatives are substrates in a number of single-carbon-transfer reactions, and also are involved in the synthesis of dTMP (2-deoxythymidine-5-phosphate) from dUMP (2-deoxyuridine-5-phosphate). It helps convert vitamin B12 to one of its coenzyme forms and helps synthesize the DNA required for all rapidly growing cells.
同义名列表
18 个代谢物同义名
(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium; (6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium; 5,10-Methenyltetrahydropteroylglutamate; 5,10-Methenyltetrahydrofolic acid; N5,N10-Methenyl tetrahydrofolate; N5-N10-Methenyltetrahydrofolate; 5,10-Methenyltetrahydrofolate; Methenyltetrahydrofolic acid; Methenyl-tetrahydrofolate; Methenyltetrahydrofolate; Anhydro-leucovorin a; Anhydroleucovorin a; Anhydro-leucovorin; 5,10-Methenyl-THF; Anhydroleucovorin; N5-N10-CH-THF; Methenyl-THF; CH-THF
数据库引用编号
10 个数据库交叉引用编号
- PubChem: 135450599
- HMDB: HMDB0001354
- Wikipedia: 5,10-Methenyltetrahydrofolate
- KNApSAcK: C00019687
- foodb: FDB022573
- chemspider: 559356
- CAS: 7444-29-3
- PMhub: MS000016874
- RefMet: 5,10-Methenyl-THF
- RefMet: Methenyl-THF
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(2)
- Folate metabolism:
Thromboxane A2 ⟶ Thromboxane B2
- Folate metabolism:
Thromboxane A2 ⟶ Thromboxane B2
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
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。
亚细胞结构定位 | 关联基因列表 |
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文献列表
- Tanja Göbel, Stefan Reisbacher, Alfred Batschauer, Richard Pokorny. Flavin Adenine Dinucleotide and N5 ,N10 -Methenyltetrahydrofolate are the in planta Cofactors of Arabidopsis thaliana Cryptochrome 3.
Photochemistry and photobiology.
2017 01; 93(1):355-362. doi:
10.1111/php.12622
. [PMID: 27463507] - Christine M Pfeiffer, Maya R Sternberg, Zia Fazili, David A Lacher, Mindy Zhang, Clifford L Johnson, Heather C Hamner, Regan L Bailey, Jeanne I Rader, Sedigheh Yamini, R J Berry, Elizabeth A Yetley. Folate status and concentrations of serum folate forms in the US population: National Health and Nutrition Examination Survey 2011-2.
The British journal of nutrition.
2015 Jun; 113(12):1965-77. doi:
10.1017/s0007114515001142
. [PMID: 25917925] - Patrick Scheerer, Fan Zhang, Jacqueline Kalms, David von Stetten, Norbert Krauß, Inga Oberpichler, Tilman Lamparter. The class III cyclobutane pyrimidine dimer photolyase structure reveals a new antenna chromophore binding site and alternative photoreduction pathways.
The Journal of biological chemistry.
2015 May; 290(18):11504-14. doi:
10.1074/jbc.m115.637868
. [PMID: 25784552] - Zia Fazili, Ralph D Whitehead, Neelima Paladugula, Christine M Pfeiffer. A high-throughput LC-MS/MS method suitable for population biomonitoring measures five serum folate vitamers and one oxidation product.
Analytical and bioanalytical chemistry.
2013 May; 405(13):4549-60. doi:
10.1007/s00216-013-6854-9
. [PMID: 23462981] - Mara L Becker, Leon van Haandel, Roger Gaedigk, Bradley Thomas, Mark F Hoeltzel, Andrew Lasky, Hongying Dai, John Stobaugh, James S Leeder. Red blood cell folate concentrations and polyglutamate distribution in juvenile arthritis: predictors of folate variability.
Pharmacogenetics and genomics.
2012 Apr; 22(4):236-46. doi:
10.1097/fpc.0b013e3283500202
. [PMID: 22344247] - Julia Moldt, Richard Pokorny, Christian Orth, Uwe Linne, Yann Geisselbrecht, Mohamed A Marahiel, Lars-Oliver Essen, Alfred Batschauer. Photoreduction of the folate cofactor in members of the photolyase family.
The Journal of biological chemistry.
2009 Aug; 284(32):21670-83. doi:
10.1074/jbc.m109.018697
. [PMID: 19531478] - Aymeric Goyer, Eva Collakova, Rocío Díaz de la Garza, Eoin P Quinlivan, Jerry Williamson, Jesse F Gregory, Yair Shachar-Hill, Andrew D Hanson. 5-Formyltetrahydrofolate is an inhibitory but well tolerated metabolite in Arabidopsis leaves.
The Journal of biological chemistry.
2005 Jul; 280(28):26137-42. doi:
10.1074/jbc.m503106200
. [PMID: 15888445] - J E Baggott, T Tamura. Bioactivity of orally administered unnatural isomers, [6R]-5-formyltetrahydrofolate and [6S]-5,10-methenyltetrahydrofolate, in humans.
Biochimica et biophysica acta.
1999 Oct; 1472(1-2):323-32. doi:
10.1016/s0304-4165(99)00135-x
. [PMID: 10572954] - R Ghosh, S Biswas, S Roy. An apyrase from Mimosa pudica contains N5,N10-methenyl tetrahydrofolate and is stimulated by light.
European journal of biochemistry.
1998 Dec; 258(3):1009-13. doi:
10.1046/j.1432-1327.1998.2581009.x
. [PMID: 9990319] - J A Houghton, L G Williams, S K Loftin, P J Cheshire, C L Morton, P J Houghton, A Dayan, J Jolivet. Factors that influence the therapeutic activity of 5-fluorouracil [6RS]leucovorin combinations in colon adenocarcinoma xenografts.
Cancer chemotherapy and pharmacology.
1992; 30(6):423-32. doi:
10.1007/bf00685592
. [PMID: 1394798] - J L Johnson, S Hamm-Alvarez, G Payne, G B Sancar, K V Rajagopalan, A Sancar. Identification of the second chromophore of Escherichia coli and yeast DNA photolyases as 5,10-methenyltetrahydrofolate.
Proceedings of the National Academy of Sciences of the United States of America.
1988 Apr; 85(7):2046-50. doi:
10.1073/pnas.85.7.2046
. [PMID: 2895469]