(6S)-5,6,7,8-Tetrahydrofolate (BioDeep_00001868885)
Main id: BioDeep_00000229169
BioNovoGene_Lab2019
代谢物信息卡片
(6S)-5,6,7,8-Tetrahydrofolate
化学式: C19H23N7O6 (445.171)
中文名称: 四氢叶酸
谱图信息:
最多检出来源 () 0%
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)/t11-,12-/m0/s1
分类词条
相关代谢途径
Reactome(9)
- Metabolism
- Metabolism of vitamins and cofactors
- Metabolism of proteins
- Amino acid and derivative metabolism
- Glyoxylate metabolism and glycine degradation
- Histidine, lysine, phenylalanine, tyrosine, proline and tryptophan catabolism
- Metabolism of water-soluble vitamins and cofactors
- Glycine degradation
- Metabolism of folate and pterines
BioCyc(15)
- purine nucleotides de novo biosynthesis I
- superpathway of histidine, purine, and pyrimidine biosynthesis
- purine nucleotides de novo biosynthesis II
- methionine biosynthesis
- superpathway of threonine degradation
- glycine cleavage complex
- glycine degradation III
- superpathway of lysine, threonine and methionine biosynthesis I
- formylTHF biosynthesis II
- formylTHF biosynthesis I
- methionine biosynthesis I
- tetrahydrofolate biosynthesis I
- folate polyglutamylation I
- folate metabolism
- threonine degradation I
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)
1 个相关的物种来源信息
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
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
- 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] - 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] - 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] - 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] - Jeong-hwa Choi, Zoe Yates, Charlotte Martin, Lyndell Boyd, Xiaowei Ng, Virginia Skinner, Ron Wai, Martin Veysey, Mark Lucock. Gene-Nutrient Interaction between Folate and Dihydrofolate Reductase in Risk for Adenomatous Polyp Occurrence: A Preliminary Report.
Journal of nutritional science and vitaminology.
2015; 61(6):455-9. doi:
10.3177/jnsv.61.455. [PMID: 26875486] - Fabiola Castorena-Torres, Perla A Ramos-Parra, Rogelio V Hernández-Méndez, Andrés Vargas-García, Gerardo García-Rivas, Rocío I Díaz de la Garza. Natural folates from biofortified tomato and synthetic 5-methyl-tetrahydrofolate display equivalent bioavailability in a murine model.
Plant foods for human nutrition (Dordrecht, Netherlands).
2014 Mar; 69(1):57-64. doi:
10.1007/s11130-013-0402-9. [PMID: 24445671] - Susanne H Kirsch, Wolfgang Herrmann, Jürgen Geisel, Rima Obeid. Assay of whole blood (6S)-5-CH3-H4folate using ultra performance liquid chromatography tandem mass spectrometry.
Analytical and bioanalytical chemistry.
2012 Aug; 404(3):895-902. doi:
10.1007/s00216-012-6180-7. [PMID: 22729356] - 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] - 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] - Steven W Bailey, June E Ayling. The extremely slow and variable activity of dihydrofolate reductase in human liver and its implications for high folic acid intake.
Proceedings of the National Academy of Sciences of the United States of America.
2009 Sep; 106(36):15424-9. doi:
10.1073/pnas.0902072106. [PMID: 19706381] - Yong Wang, Hong-Yang Zhang, Qiong-Lin Liang, Hui-Hua Yang, Yi-Ming Wang, Qing-Fei Liu, Ping Hu, Xiao-Ying Zheng, Xin-Ming Song, Gong Chen, Ting Zhang, Jian-Xin Wu, Guo-An Luo. Simultaneous quantification of 11 pivotal metabolites in neural tube defects by HPLC-electrospray tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2008 Feb; 863(1):94-100. doi:
10.1016/j.jchromb.2008.01.010. [PMID: 18243823] - M Righetti. [Folate metabolism dysfunction].
Giornale italiano di nefrologia : organo ufficiale della Societa italiana di nefrologia.
2008 Jan; 25(1):32-41. doi:
NULL. [PMID: 18264916] - Jong-Sik Jin, Yu-Feng Zhao, Norio Nakamura, Teruaki Akao, Nobuko Kakiuchi, Masao Hattori. Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone.
Biological & pharmaceutical bulletin.
2007 May; 30(5):904-11. doi:
10.1248/bpb.30.904. [PMID: 17473433] - Johan D M Patring, Jelena A Jastrebova, Sofia B Hjortmo, Thomas A Andlid, I Margaretha Jägerstad. Development of a simplified method for the determination of folates in baker's yeast by HPLC with ultraviolet and fluorescence detection.
Journal of agricultural and food chemistry.
2005 Apr; 53(7):2406-11. doi:
10.1021/jf048083g. [PMID: 15796570] - Marlies K Ozias, Kevin L Schalinske. All-trans-retinoic acid rapidly induces glycine N-methyltransferase in a dose-dependent manner and reduces circulating methionine and homocysteine levels in rats.
The Journal of nutrition.
2003 Dec; 133(12):4090-4. doi:
10.1093/jn/133.12.4090. [PMID: 14652353] - A F Harper, J W Knight, E Kokue, J L Usry. Plasma reduced folates, reproductive performance, and conceptus development in sows in response to supplementation with oxidized and reduced sources of folic acid.
Journal of animal science.
2003 Mar; 81(3):735-44. doi:
10.2527/2003.813735x. [PMID: 12661654] - J L Vallet, R K Christenson, H G Klemcke, P L Pearson. Intravenous infusion of iron and tetrahydrofolate does not influence intrauterine uteroferrin and secreted folate-binding protein content in swine.
Journal of animal science.
2001 Jan; 79(1):188-92. doi:
10.2527/2001.791188x. [PMID: 11204699] - K Nilsson, L Gustafson, B Hultberg. Plasma homocysteine is a sensitive marker for tissue deficiency of both cobalamines and folates in a psychogeriatric population.
Dementia and geriatric cognitive disorders.
1999 Nov; 10(6):476-82. doi:
10.1159/000017193. [PMID: 10559563] - E J Kim, N S Kim, G M Lee. Development of a serum-free medium for the production of humanized antibody from Chinese hamster ovary cells using a statistical design.
In vitro cellular & developmental biology. Animal.
1998 Nov; 34(10):757-61. doi:
10.1007/s11626-998-0029-6. [PMID: 9870524] - L Hullán, L Trézl, T Szarvas, A Csiba. The hydrazine derivative aminoguanidine inhibits the reaction of tetrahydrofolic acid with hydroxymethylarginine biomolecule.
Acta biologica Hungarica.
1998; 49(2-4):265-73. doi:
NULL. [PMID: 10526969] - E Odin, G Carlsson, R Frösing, B Gustavsson, C P Spears, P A Larsson. Chemical stability and human plasma pharmacokinetics of reduced folates.
Cancer investigation.
1998; 16(7):447-55. doi:
10.3109/07357909809011698. [PMID: 9774951] - D W Kim, S Delle Fratte, S S Jeong, V Schirch. Determination of serine hydroxymethyltransferase and reduced folate pools in tissue extracts.
Analytical biochemistry.
1997 Nov; 253(2):201-9. doi:
10.1006/abio.1997.2388. [PMID: 9367504] - L T Vahteristo, V Ollilainen, P Varo. Liquid chromatographic determination of folate monoglutamates in fish, meat, egg, and dairy products consumed in Finland.
Journal of AOAC International.
1997 Mar; 80(2):373-8. doi:
10.1093/jaoac/80.2.373. [PMID: 9086593] - M Natsuhori, M Shimoda, E Kokue. Alteration of plasma folates in gestating sows and newborn piglets.
The American journal of physiology.
1996 Jan; 270(1 Pt 2):R99-104. doi:
10.1152/ajpregu.1996.270.1.r99. [PMID: 8769790] - K Sasaki, M Natsuhori, M Shimoda, Y Saima, E Kokue. Role of high-affinity folate-binding protein in the plasma distribution of tetrahydrofolate in pigs.
The American journal of physiology.
1996 Jan; 270(1 Pt 2):R105-10. doi:
10.1152/ajpregu.1996.270.1.r105. [PMID: 8769791] - T Hashimoto, K Omura, T Sunohara, A Osari, T Yasuda, K Kawakami, T Matsu, F Ishida, Y Watanabe, M Fukushima. [Pharmacokinetics and changes of reduced folate levels in tumor after administration of cisplatin].
Gan to kagaku ryoho. Cancer & chemotherapy.
1994 May; 21(6):859-64. doi:
NULL. [PMID: 8185345] - H Müller. [The determination of the folic acid content of foods of animal origin using high performance liquid chromatography (HPLC)].
Zeitschrift fur Lebensmittel-Untersuchung und -Forschung.
1993 Jun; 196(6):518-21. doi:
10.1007/bf01201330. [PMID: 8328216] - K Sasaki, M Shimoda, Y Aoki, M Natsuhori, E Kokue. Contribution of plasma protein binding to the stability of tetrahydrofolate in pig plasma.
Advances in experimental medicine and biology.
1993; 338(?):749-52. doi:
10.1007/978-1-4615-2960-6_156. [PMID: 8304221] - M Natsuhori, E Kokue, M Shimoda. Influence of gestation and lactation on the levels of plasma folates in sows.
Advances in experimental medicine and biology.
1993; 338(?):733-6. doi:
10.1007/978-1-4615-2960-6_152. [PMID: 8304217] - L H Matherly, S M Angeles, C A Czajkowski. Characterization of transport-mediated methotrexate resistance in human tumor cells with antibodies to the membrane carrier for methotrexate and tetrahydrofolate cofactors.
The Journal of biological chemistry.
1992 Nov; 267(32):23253-60. doi:
10.1016/s0021-9258(18)50084-3. [PMID: 1429671] - M Shimoda. Simultaneous determination of tetrahydrofolate and N5-methyltetrahydrofolate in pig plasma by high-performance liquid chromatography with electrochemical detection.
The Journal of veterinary medical science.
1992 Apr; 54(2):249-53. doi:
10.1292/jvms.54.249. [PMID: 1606254] - D G Priest, J C Schmitz, M A Bunni, R K Stuart. Pharmacokinetics of leucovorin metabolites in human plasma as a function of dose administered orally and intravenously.
Journal of the National Cancer Institute.
1991 Dec; 83(24):1806-12. doi:
10.1093/jnci/83.24.1806. [PMID: 1744924] - M Natsuhori, M Shimoda, E Kokue, T Hayama, Y Takahashi. Tetrahydrofolic acid as the principal congener of plasma folates in pigs.
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10.1152/ajpregu.1991.261.1.r82. [PMID: 1858958] - M Marchetti. [Folate determination in serum for clinical use (author's transl)].
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