N6,N6,N6-Trimethyl-L-lysine (BioDeep_00001868880)
Main id: BioDeep_00000003910
代谢物信息卡片
N6,N6,N6-Trimethyl-L-lysine
化学式: C9H20N2O2 (188.1525)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C[N+](C)(C)CCCCC(C(=O)[O-])N
InChI: InChI=1S/C9H20N2O2/c1-11(2,3)7-5-4-6-8(10)9(12)13/h8H,4-7,10H2,1-3H3/t8-/m0/s1
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:165870
- KEGG: C03793
- PubChem: 440120
- CAS: 23284-33-5
- PubChem: 6542
- PDB-CCD: M3L
- 3DMET: B01691
- NIKKAJI: J839.325G
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
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)
0 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
- Haoran Wei, Mingming Zhao, Junfang Wu, Chenze Li, Man Huang, Jianing Gao, Qi Zhang, Liang Ji, Yan Wang, Chunxia Zhao, Erdan Dong, Lemin Zheng, Dao Wen Wang. Association of Systemic Trimethyllysine With Heart Failure With Preserved Ejection Fraction and Cardiovascular Events.
The Journal of clinical endocrinology and metabolism.
2022 11; 107(12):e4360-e4370. doi:
10.1210/clinem/dgac519. [PMID: 36062477] - Jie Xu, Mingming Zhao, Anxin Wang, Jing Xue, Si Cheng, Aichun Cheng, Jianing Gao, Qi Zhang, Rui Zhan, Xia Meng, Ming Xu, Hao Li, Lemin Zheng, Yongjun Wang. Association Between Plasma Trimethyllysine and Prognosis of Patients With Ischemic Stroke.
Journal of the American Heart Association.
2021 12; 10(23):e020979. doi:
10.1161/jaha.121.020979. [PMID: 34816729] - Edzard Schwedhelm, Mirjam von Lucadou, Sven Peine, Susanne Lezius, Götz Thomalla, Rainer Böger, Christian Gerloff, Chi-Un Choe. Trimethyllysine, vascular risk factors and outcome in acute ischemic stroke (MARK-STROKE).
Amino acids.
2021 Apr; 53(4):555-561. doi:
10.1007/s00726-021-02969-x. [PMID: 33788002] - E Ø Bjørnestad, H Olset, I Dhar, K Løland, E K R Pedersen, G F T Svingen, A Svardal, R K Berge, P M Ueland, G S Tell, D W T Nilsen, J E Nordrehaug, E Nygaard, O Nygård. Circulating trimethyllysine and risk of acute myocardial infarction in patients with suspected stable coronary heart disease.
Journal of internal medicine.
2020 10; 288(4):446-456. doi:
10.1111/joim.13067. [PMID: 32270523] - Xinmin S Li, Slayman Obeid, Zeneng Wang, Benjamin J Hazen, Lin Li, Yuping Wu, Alex G Hurd, Xiaodong Gu, Alan Pratt, Bruce S Levison, Yoon-Mi Chung, Steven E Nissen, Wai Hong Wilson Tang, François Mach, Lorenz Räber, David Nanchen, Christian M Matter, Thomas F Lüscher, Stanley L Hazen. Trimethyllysine, a trimethylamine N-oxide precursor, provides near- and long-term prognostic value in patients presenting with acute coronary syndromes.
European heart journal.
2019 08; 40(32):2700-2709. doi:
10.1093/eurheartj/ehz259. [PMID: 31049589] - Xinmin S Li, Zeneng Wang, Tomas Cajka, Jennifer A Buffa, Ina Nemet, Alex G Hurd, Xiaodong Gu, Sarah M Skye, Adam B Roberts, Yuping Wu, Lin Li, Christopher J Shahen, Matthew A Wagner, Jaana A Hartiala, Robert L Kerby, Kymberleigh A Romano, Yi Han, Slayman Obeid, Thomas F Lüscher, Hooman Allayee, Federico E Rey, Joseph A DiDonato, Oliver Fiehn, W H Wilson Tang, Stanley L Hazen. Untargeted metabolomics identifies trimethyllysine, a TMAO-producing nutrient precursor, as a predictor of incident cardiovascular disease risk.
JCI insight.
2018 03; 3(6):. doi:
10.1172/jci.insight.99096. [PMID: 29563342] - Elin Strand, Eirik W Rebnord, Malin R Flygel, Vegard Lysne, Gard F T Svingen, Grethe S Tell, Kjetil H Løland, Rolf K Berge, Asbjørn Svardal, Ottar Nygård, Eva R Pedersen. Serum Carnitine Metabolites and Incident Type 2 Diabetes Mellitus in Patients With Suspected Stable Angina Pectoris.
The Journal of clinical endocrinology and metabolism.
2018 03; 103(3):1033-1041. doi:
10.1210/jc.2017-02139. [PMID: 29325058] - Karolina Skagen, Marius Trøseid, Thor Ueland, Sverre Holm, Azhar Abbas, Ida Gregersen, Martin Kummen, Vigdis Bjerkeli, Frode Reier-Nilsen, David Russell, Asbjørn Svardal, Tom Hemming Karlsen, Pål Aukrust, Rolf K Berge, Johannes E R Hov, Bente Halvorsen, Mona Skjelland. The Carnitine-butyrobetaine-trimethylamine-N-oxide pathway and its association with cardiovascular mortality in patients with carotid atherosclerosis.
Atherosclerosis.
2016 Apr; 247(?):64-9. doi:
10.1016/j.atherosclerosis.2016.01.033. [PMID: 26868510] - Hillary F Allen, Kevin D Daze, Takashi Shimbo, Anne Lai, Catherine A Musselman, Jennifer K Sims, Paul A Wade, Fraser Hof, Tatiana G Kutateladze. Inhibition of histone binding by supramolecular hosts.
The Biochemical journal.
2014 May; 459(3):505-12. doi:
10.1042/bj20140145. [PMID: 24576085] - Luigi Servillo, Alfonso Giovane, Domenico Cautela, Domenico Castaldo, Maria Luisa Balestrieri. Where does N(ε)-trimethyllysine for the carnitine biosynthesis in mammals come from?.
PloS one.
2014; 9(1):e84589. doi:
10.1371/journal.pone.0084589. [PMID: 24454731] - Kjetil H Løland, Oyvind Bleie, Heidi Borgeraas, Elin Strand, Per M Ueland, Asbjørn Svardal, Jan E Nordrehaug, Ottar Nygård. The association between progression of atherosclerosis and the methylated amino acids asymmetric dimethylarginine and trimethyllysine.
PloS one.
2013; 8(5):e64774. doi:
10.1371/journal.pone.0064774. [PMID: 23734218] - Sonia Rippa, Yingjuan Zhao, Franck Merlier, Aurélie Charrier, Yolande Perrin. The carnitine biosynthetic pathway in Arabidopsis thaliana shares similar features with the pathway of mammals and fungi.
Plant physiology and biochemistry : PPB.
2012 Nov; 60(?):109-14. doi:
10.1016/j.plaphy.2012.08.001. [PMID: 22922110] - Robert Ringseis, Nicole Hanisch, Gregor Seliger, Klaus Eder. Low availability of carnitine precursors as a possible reason for the diminished plasma carnitine concentrations in pregnant women.
BMC pregnancy and childbirth.
2010 Apr; 10(?):17. doi:
10.1186/1471-2393-10-17. [PMID: 20416111] - Maren Fischer, Frank Hirche, Holger Kluge, Klaus Eder. A moderate excess of dietary lysine lowers plasma and tissue carnitine concentrations in pigs.
The British journal of nutrition.
2009 Jan; 101(2):190-6. doi:
10.1017/s0007114508994770. [PMID: 18492302] - Alexander Koch, Bettina König, Gabriele I Stangl, Klaus Eder. PPAR alpha mediates transcriptional upregulation of novel organic cation transporters-2 and -3 and enzymes involved in hepatic carnitine synthesis.
Experimental biology and medicine (Maywood, N.J.).
2008 Mar; 233(3):356-65. doi:
10.3181/0706-rm-168. [PMID: 18296741] - Robert Ringseis, Stefanie Pösel, Frank Hirche, Klaus Eder. Treatment with pharmacological peroxisome proliferator-activated receptor alpha agonist clofibrate causes upregulation of organic cation transporter 2 in liver and small intestine of rats.
Pharmacological research.
2007 Aug; 56(2):175-83. doi:
10.1016/j.phrs.2007.06.001. [PMID: 17644405] - Lynnette M A Dirk, E Megan Flynn, Kevin Dietzel, Jean-François Couture, Raymond C Trievel, Robert L Houtz. Kinetic manifestation of processivity during multiple methylations catalyzed by SET domain protein methyltransferases.
Biochemistry.
2007 Mar; 46(12):3905-15. doi:
10.1021/bi6023644. [PMID: 17338551] - Jean-François Couture, Glenn Hauk, Mark J Thompson, G Michael Blackburn, Raymond C Trievel. Catalytic roles for carbon-oxygen hydrogen bonding in SET domain lysine methyltransferases.
The Journal of biological chemistry.
2006 Jul; 281(28):19280-7. doi:
10.1074/jbc.m602257200. [PMID: 16682405] - Alan T Davis, Thomas J Monroe. Carnitine deficiency and supplementation do not affect the gene expression of carnitine biosynthetic enzymes in rats.
The Journal of nutrition.
2005 Apr; 135(4):761-4. doi:
10.1093/jn/135.4.761. [PMID: 15795431] - Frédéric M Vaz, Bela Melegh, Judit Bene, Dean Cuebas, Douglas A Gage, Albert Bootsma, Peter Vreken, Albert H van Gennip, Loran L Bieber, Ronald J A Wanders. Analysis of carnitine biosynthesis metabolites in urine by HPLC-electrospray tandem mass spectrometry.
Clinical chemistry.
2002 Jun; 48(6 Pt 1):826-34. doi:
. [PMID: 12028997] - S Krähenbühl, E P Brass, C L Hoppel. Decreased carnitine biosynthesis in rats with secondary biliary cirrhosis.
Hepatology (Baltimore, Md.).
2000 Jun; 31(6):1217-23. doi:
10.1053/jhep.2000.8105. [PMID: 10827145] - N Terada, F Inoue, M Okochi, H Nakajima, Z Kizaki, A Kinugasa, T Sawada. Measurement of carnitine precursors, epsilon-trimethyllysine and gamma-butyrobetaine in human serum by tandem mass spectrometry.
Journal of chromatography. B, Biomedical sciences and applications.
1999 Aug; 731(1):89-95. doi:
10.1016/s0378-4347(99)00112-7. [PMID: 10491993] - B Melegh, G Tóth, K Adamovich, G Szekely, D A Gage, L L Bieber. Labeled trimethyllysine load depletes unlabeled carnitine in premature infants without evidence of incorporation.
Biology of the neonate.
1999 Jul; 76(1):19-25. doi:
10.1159/000014127. [PMID: 10364635] - M L Katz. Decreased plasma carnitine and trimethyl-L-lysine levels associated with lysosomal accumulation of a trimethyl-L-lysine containing protein in Batten disease.
Biochimica et biophysica acta.
1996 Dec; 1317(3):192-8. doi:
10.1016/s0925-4439(96)00054-3. [PMID: 8988235] - B Melegh, R Hermann, I Bock. Generation of hydroxytrimethyllysine from trimethyllysine limits the carnitine biosynthesis in premature infants.
Acta paediatrica (Oslo, Norway : 1992).
1996 Mar; 85(3):345-50. doi:
10.1111/j.1651-2227.1996.tb14030.x. [PMID: 8695994] - M L Katz, A N Siakotos. Canine hereditary ceroid-lipofuscinosis: evidence for a defect in the carnitine biosynthetic pathway.
American journal of medical genetics.
1995 Jun; 57(2):266-71. doi:
10.1002/ajmg.1320570231. [PMID: 7668343] - M L Katz, J S Christianson, N E Norbury, C L Gao, A N Siakotos, N Koppang. Lysine methylation of mitochondrial ATP synthase subunit c stored in tissues of dogs with hereditary ceroid lipofuscinosis.
The Journal of biological chemistry.
1994 Apr; 269(13):9906-11. doi:
10.1016/s0021-9258(17)36968-5. [PMID: 8144584] - B Melegh, M Pap, I Bock, C J Rebouche. Relationship of carnitine and carnitine precursors lysine, epsilon-N-trimethyllysine, and gamma-butyrobetaine in drug-induced carnitine depletion.
Pediatric research.
1993 Oct; 34(4):460-4. doi:
10.1203/00006450-199310000-00015. [PMID: 8255678] - A T Davis, E M Kruggel, S Randall. Excess dietary lysine increases skeletal muscle and plasma trimethyllysine in rats.
The Journal of nutrition.
1993 Jun; 123(6):1109-16. doi:
10.1093/jn/123.6.1109. [PMID: 8505672] - M Mizobuchi, M Miyake, A Sano, Y Kakimoto. High concentration of free trimethyllysine in red blood cells.
Biochimica et biophysica acta.
1990 Feb; 1033(2):119-23. doi:
10.1016/0304-4165(90)90001-d. [PMID: 2106342] - C J Rebouche, E P Bosch, C A Chenard, K J Schabold, S E Nelson. Utilization of dietary precursors for carnitine synthesis in human adults.
The Journal of nutrition.
1989 Dec; 119(12):1907-13. doi:
10.1093/jn/119.12.1907. [PMID: 2516120] - C Vijayasarathy, L Khan-Siddiqui, S N Murthy, M S Bamji. Rise in plasma trimethyllysine levels in humans after oral lysine load.
The American journal of clinical nutrition.
1987 Nov; 46(5):772-7. doi:
10.1093/ajcn/46.5.772. [PMID: 3118695] - K P Kohse, T A Graser, P Fürst, H E Franz. Plasma levels of carnitine precursor 6-N-trimethyllysine and maintenance hemodialysis.
Kidney international. Supplement.
1987 Oct; 22(?):S128-31. doi:
NULL. [PMID: 3123762] - A L Olson, C J Rebouche. gamma-Butyrobetaine hydroxylase activity is not rate limiting for carnitine biosynthesis in the human infant.
The Journal of nutrition.
1987 Jun; 117(6):1024-31. doi:
10.1093/jn/117.6.1024. [PMID: 3110383] - L J Lehman, A L Olson, C J Rebouche. Measurement of epsilon-N-trimethyllysine in human blood plasma and urine.
Analytical biochemistry.
1987 Apr; 162(1):137-42. doi:
10.1016/0003-2697(87)90018-2. [PMID: 3111294] - H S Paul, C E Gleditsch, S A Adibi. Mechanism of increased hepatic concentration of carnitine by clofibrate.
The American journal of physiology.
1986 Sep; 251(3 Pt 1):E311-5. doi:
10.1152/ajpendo.1986.251.3.e311. [PMID: 3092678] - P E Minkler, E A Erdos, S T Ingalls, R L Griffin, C L Hoppel. Improved high-performance liquid chromatographic method for the determination of 6-N,N,N-trimethyllysine in plasma and urine: biomedical application of chromatographic figures of merit and amine mobile phase modifiers.
Journal of chromatography.
1986 Aug; 380(2):285-99. doi:
10.1016/s0378-4347(00)83657-9. [PMID: 3093513] - C L Hoppel, A T Davis. Inter-tissue relationships in the synthesis and distribution of carnitine.
Biochemical Society transactions.
1986 Aug; 14(4):673-4. doi:
10.1042/bst0140673. [PMID: 3091422] - C Wanner, W H Hörl. Potential role of carnitine in patients with renal insufficiency.
Klinische Wochenschrift.
1986 Jul; 64(13):579-86. doi:
10.1007/bf01735259. [PMID: 3091903] - A T Davis, C L Hoppel. Effect of starvation on the disposition of free and peptide-linked trimethyllysine in the rat.
The Journal of nutrition.
1986 May; 116(5):760-7. doi:
10.1093/jn/116.5.760. [PMID: 3084727] - C J Rebouche, L J Lehman, L Olson. epsilon-N-trimethyllysine availability regulates the rate of carnitine biosynthesis in the growing rat.
The Journal of nutrition.
1986 May; 116(5):751-9. doi:
10.1093/jn/116.5.751. [PMID: 3084726] - K P Kohse, T A Graser, H G Godel, C Rössle, H E Franz, P Fürst. High-performance liquid chromatographic determination of plasma free trimethyllysine in humans.
Journal of chromatography.
1985 Nov; 344(?):319-24. doi:
10.1016/s0378-4347(00)82034-4. [PMID: 3936857] - W A Dunn, G Rettura, E Seifter, S Englard. Carnitine biosynthesis from gamma-butyrobetaine and from exogenous protein-bound 6-N-trimethyl-L-lysine by the perfused guinea pig liver. Effect of ascorbate deficiency on the in situ activity of gamma-butyrobetaine hydroxylase.
The Journal of biological chemistry.
1984 Sep; 259(17):10764-70. doi:
10.1016/s0021-9258(18)90577-6. [PMID: 6432788] - A T Davis, S T Ingalls, C L Hoppel. Determination of free trimethyllysine in plasma and tissue specimens by high-performance liquid chromatography.
Journal of chromatography.
1984 Mar; 306(?):79-87. doi:
10.1016/s0378-4347(00)80871-3. [PMID: 6425353] - A T Davis, C L Hoppel. Effect of starvation in the rat on trimethyllysine in peptide linkage.
The Journal of nutrition.
1983 May; 113(5):979-85. doi:
10.1093/jn/113.5.979. [PMID: 6405021] - C L Hoppel, D E Weir, A P Gibbons, S T Ingalls, A T Brittain, F M Brown. Determination of 6-N-trimethyllysine in urine by high-performance liquid chromatography.
Journal of chromatography.
1983 Jan; 272(1):43-50. doi:
10.1016/s0378-4347(00)86101-0. [PMID: 6404917] - L M Henderson, P J Nelson, L Henderson. Mammalian enzymes of trimethyllysine conversion to trimethylaminobutyrate.
Federation proceedings.
1982 Oct; 41(12):2843-7. doi:
. [PMID: 6813145] - C J Rebouche. Sites and regulation of carnitine biosynthesis in mammals.
Federation proceedings.
1982 Oct; 41(12):2848-52. doi:
NULL. [PMID: 6813146] - R Stein, S Englard. Properties of rat 6-N-trimethyl-L-lysine hydroxylases: similarities among the kidney, liver, heart, and skeletal muscle activities.
Archives of biochemistry and biophysics.
1982 Aug; 217(1):324-31. doi:
10.1016/0003-9861(82)90508-2. [PMID: 6812504] - H P Broquist, P R Borum. Carnitine biosynthesis: nutritional implications.
Advances in nutritional research.
1982; 4(?):181-204. doi:
10.1007/978-1-4613-9934-6_7. [PMID: 6801934] - R Stein, S Englard. The use of a tritium release assay to measure 6-N-trimethyl-L-lysine hydroxylase activity: synthesis of 6-N-[3-3H]trimethyl-DL-lysine.
Analytical biochemistry.
1981 Sep; 116(1):230-6. doi:
10.1016/0003-2697(81)90349-3. [PMID: 6795966] - C J Rebouche, A G Engel. Primary systemic carnitine deficiency: I. Carnitine biosynthesis.
Neurology.
1981 Jul; 31(7):813-8. doi:
10.1212/wnl.31.7.813. [PMID: 6787460] - P J Nelson, R E Pruitt, L L Henderson, R Jenness, L M Henderson. Effect of ascorbic acid deficiency on the in vivo synthesis of carnitine.
Biochimica et biophysica acta.
1981 Jan; 672(1):123-7. doi:
10.1016/0304-4165(81)90286-5. [PMID: 6783120] - C J Rebouche, A G Engel. Significance of renal gamma-butyrobetaine hydroxylase for carnitine biosynthesis in man.
The Journal of biological chemistry.
1980 Sep; 255(18):8700-5. doi:
10.1016/s0021-9258(18)43556-9. [PMID: 6773946] - C J Rebouche, A G Engel. Tissue distribution of carnitine biosynthetic enzymes in man.
Biochimica et biophysica acta.
1980 Jun; 630(1):22-9. doi:
10.1016/0304-4165(80)90133-6. [PMID: 6770910] - D S Sachan, C L Hoppel. Carnitine biosynthesis. Hydroxylation of N6-trimethyl-lysine to 3-hydroxy-N6-trimethyl-lysine.
The Biochemical journal.
1980 May; 188(2):529-34. doi:
10.1042/bj1880529. [PMID: 6772170] - C L Hoppel, R A Cox, R F Novak. N6-Trimethyl-lysine metabolism. 3-Hydroxy-N6-trimethyl-lysine and carnitine biosynthesis.
The Biochemical journal.
1980 May; 188(2):509-19. doi:
10.1042/bj1880509. [PMID: 6772168] - Y S Kim, M F Lou, M K Paik, S Kim, W K Paik. Methylation of nuclear proteins of Novikoff hepatoma.
Carcinogenesis.
1980 Feb; 1(2):129-34. doi:
10.1093/carcin/1.2.129. [PMID: 22282991] - A L Carter, R Frenkel. The role of the kidney in the biosynthesis of carnitine in the rat.
The Journal of biological chemistry.
1979 Nov; 254(21):10670-4. doi:
10.1016/s0021-9258(19)86572-9. [PMID: 500604]
