4-Trimethylammoniobutanoate (BioDeep_00000002995)
BioNovoGene_Lab2019
代谢物信息卡片
化学式: C7H16NO2+ (146.1181)
中文名称: 海葵碱, (3-羧丙基)三甲基氯化铵
谱图信息:
最多检出来源 Homo sapiens(lipidsearch) 7.8%
分子结构信息
SMILES: C[N+](C)(C)CCCC(=O)O
InChI: InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3/p+1
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:1941
- KEGG: C01181
- PubChem: 134
- CAS: 10329-41-6
- PubChem: 4408
- PDB-CCD: NM2
- 3DMET: B00256
- NIKKAJI: J38.536K
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-194
分类词条
相关代谢途径
Reactome()
BioCyc()
PlantCyc()
代谢反应
7 个相关的代谢反应过程信息。
Reactome()
BioCyc()
WikiPathways()
Plant Reactome()
INOH(3)
- Lysine degradation ( Lysine degradation ):
2-Oxo-glutaric acid + L-Lysine + NADH ⟶ H2O + L-Saccharopine + NAD+ - NAD+ + 4-Trimethyl-ammonio-butanal + H2O = NADH + 4-Trimethyl-ammonio-butanoic acid ( Lysine degradation ):
4-Trimethyl-ammonio-butanal + H2O + NAD+ ⟶ 4-Trimethyl-ammonio-butanoic acid + NADH - NAD+ + 4-Trimethyl-ammonio-butanal + H2O = NADH + 4-Trimethyl-ammonio-butanoic acid ( Lysine degradation ):
4-Trimethyl-ammonio-butanal + H2O + NAD+ ⟶ 4-Trimethyl-ammonio-butanoic acid + NADH
PlantCyc()
COVID-19 Disease Map()
PathBank(4)
- Carnitine Synthesis:
4-Trimethylammoniobutanoic acid + Oxoglutaric acid + Oxygen ⟶ Carbon dioxide + L-Carnitine + Succinic acid - Carnitine Synthesis:
4-Trimethylammoniobutanoic acid + Oxoglutaric acid + Oxygen ⟶ Carbon dioxide + L-Carnitine + Succinic acid - Carnitine Synthesis:
4-Trimethylammoniobutanoic acid + Oxoglutaric acid + Oxygen ⟶ Carbon dioxide + L-Carnitine + Succinic acid - Carnitine Synthesis:
4-Trimethylammoniobutanoic acid + Oxoglutaric acid + Oxygen ⟶ Carbon dioxide + L-Carnitine + Succinic acid
PharmGKB()
1 个相关的物种来源信息
- 4896 - Schizosaccharomyces pombe: 10.1039/C4MB00346B
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 | |
|---|---|---|
| plasma membrane | 1 | BCHE |
| extracellular space | 1 | BCHE |
| Secreted | 1 | BCHE |
| extracellular region | 1 | BCHE |
| blood microparticle | 1 | BCHE |
| endoplasmic reticulum lumen | 1 | BCHE |
| nuclear envelope lumen | 1 | BCHE |
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] - Florian Jacques, Yingjuan Zhao, Martina Kopečná, Radka Končitíková, David Kopečný, Sonia Rippa, Yolande Perrin. Roles for ALDH10 enzymes in γ-butyrobetaine synthesis, seed development, germination, and salt tolerance in Arabidopsis.
Journal of experimental botany.
2020 12; 71(22):7088-7102. doi:
10.1093/jxb/eraa394. [PMID: 32845293] - Pascal Bazire, Nadia Perchat, Ekaterina Darii, Christophe Lechaplais, Marcel Salanoubat, Alain Perret. Characterization of l-Carnitine Metabolism in Sinorhizobium meliloti.
Journal of bacteriology.
2019 04; 201(7):. doi:
10.1128/jb.00772-18. [PMID: 30670548] - Aarti Gautam, Seid Muhie, Nabarun Chakraborty, Allison Hoke, Duncan Donohue, Stacy Ann Miller, Rasha Hammamieh, Marti Jett. Metabolomic analyses reveal lipid abnormalities and hepatic dysfunction in non-human primate model for Yersinia pestis.
Metabolomics : Official journal of the Metabolomic Society.
2018 12; 15(1):2. doi:
10.1007/s11306-018-1457-2. [PMID: 30830480] - Bridget M Stroup, Nivedita Nair, Sangita G Murali, Katarzyna Broniowska, Fran Rohr, Harvey L Levy, Denise M Ney. Metabolomic Markers of Essential Fatty Acids, Carnitine, and Cholesterol Metabolism in Adults and Adolescents with Phenylketonuria.
The Journal of nutrition.
2018 02; 148(2):194-201. doi:
10.1093/jn/nxx039. [PMID: 29490096] - Paul E Minkler, Maria S K Stoll, Stephen T Ingalls, Janos Kerner, Charles L Hoppel. Quantitative acylcarnitine determination by UHPLC-MS/MS--Going beyond tandem MS acylcarnitine "profiles".
Molecular genetics and metabolism.
2015 Dec; 116(4):231-41. doi:
10.1016/j.ymgme.2015.10.002. [PMID: 26458767] - Reinis Vilskersts, Janis Kuka, Edgars Liepinsh, Marina Makrecka-Kuka, Kristine Volska, Elina Makarova, Eduards Sevostjanovs, Helena Cirule, Solveiga Grinberga, Maija Dambrova. Methyl-γ-butyrobetaine decreases levels of acylcarnitines and attenuates the development of atherosclerosis.
Vascular pharmacology.
2015 Sep; 72(?):101-7. doi:
10.1016/j.vph.2015.05.005. [PMID: 25989106] - Jenna Pekkinen, Kaisa Olli, Anne Huotari, Kirsti Tiihonen, Pekka Keski-Rahkonen, Marko Lehtonen, Seppo Auriola, Marjukka Kolehmainen, Hannu Mykkänen, Kaisa Poutanen, Kati Hanhineva. Betaine supplementation causes increase in carnitine metabolites in the muscle and liver of mice fed a high-fat diet as studied by nontargeted LC-MS metabolomics approach.
Molecular nutrition & food research.
2013 Nov; 57(11):1959-68. doi:
10.1002/mnfr.201300142. [PMID: 23868375] - 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:
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Therapeutic drug monitoring.
2012 Aug; 34(4):406-14. doi:
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PloS one.
2012; 7(2):e32557. doi:
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Postepy higieny i medycyny doswiadczalnej (Online).
2011 Oct; 65(?):645-53. doi:
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The Journal of pharmacy and pharmacology.
2011 Sep; 63(9):1195-201. doi:
10.1111/j.2042-7158.2011.01325.x. [PMID: 21827492] - Takeo Nakanishi, Yoko Fukuyama, Masaharu Fujita, Yoshiyuki Shirasaka, Ikumi Tamai. Carnitine precursor γ-butyrobetaine is a novel substrate of the Na(+)- and Cl(-)-dependent GABA transporter Gat2.
Drug metabolism and pharmacokinetics.
2011; 26(6):632-6. doi:
10.2133/dmpk.dmpk-11-nt-053. [PMID: 21997971] - Sonja Primassin, Ute Spiekerkoetter. ESI-MS/MS measurement of free carnitine and its precursor γ-butyrobetaine in plasma and dried blood spots from patients with organic acidurias and fatty acid oxidation disorders.
Molecular genetics and metabolism.
2010 Oct; 101(2-3):141-5. doi:
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Nature.
2010 Sep; 467(7312):233-6. doi:
10.1038/nature09310. [PMID: 20829798] - 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] - Martina Tylichová, David Kopecný, Solange Moréra, Pierre Briozzo, René Lenobel, Jacques Snégaroff, Marek Sebela. Structural and functional characterization of plant aminoaldehyde dehydrogenase from Pisum sativum with a broad specificity for natural and synthetic aminoaldehydes.
Journal of molecular biology.
2010 Mar; 396(4):870-82. doi:
10.1016/j.jmb.2009.12.015. [PMID: 20026072] - Edgars Liepinsh, Janis Kuka, Baiba Svalbe, Reinis Vilskersts, Elina Skapare, Helena Cirule, Osvalds Pugovics, Ivars Kalvinsh, Maija Dambrova. Effects of long-term mildronate treatment on cardiac and liver functions in rats.
Basic & clinical pharmacology & toxicology.
2009 Dec; 105(6):387-94. doi:
10.1111/j.1742-7843.2009.00461.x. [PMID: 19663820] - Masaharu Fujita, Takeo Nakanishi, Yuta Shibue, Daisuke Kobayashi, Richard H Moseley, Yoshiyuki Shirasaka, Ikumi Tamai. Hepatic uptake of gamma-butyrobetaine, a precursor of carnitine biosynthesis, in rats.
American journal of physiology. Gastrointestinal and liver physiology.
2009 Oct; 297(4):G681-6. doi:
10.1152/ajpgi.00238.2009. [PMID: 19679820] - U Keller, C van der Wal, G Seliger, C Scheler, F Röpke, K Eder. Carnitine status of pregnant women: effect of carnitine supplementation and correlation between iron status and plasma carnitine concentration.
European journal of clinical nutrition.
2009 Sep; 63(9):1098-105. doi:
10.1038/ejcn.2009.36. [PMID: 19491916] - Maren Fischer, Janine Keller, Frank Hirche, Holger Kluge, Robert Ringseis, Klaus Eder. Activities of gamma-butyrobetaine dioxygenase and concentrations of carnitine in tissues of pigs.
Comparative biochemistry and physiology. Part A, Molecular & integrative physiology.
2009 Jul; 153(3):324-31. doi:
10.1016/j.cbpa.2009.03.005. [PMID: 19285565] - Lida Bagdoniene, Danute Labeikyte, Ivars Kalviņs, Veronika Borutinskaite, Aleksandrs Prokofjevs, Pēteris Trapencieris, Benediktas Juodka, Nikolajs Sjakste. Rat serum carboxylesterase partly hydrolyses gamma-butyrobetaine esters.
Arhiv za higijenu rada i toksikologiju.
2009 Jun; 60(2):147-56. doi:
10.2478/10004-1254-60-2009-1915. [PMID: 19581207] - Marta García-Delgado, María J Peral, Juan M Durán, Pablo García-Miranda, Maria L Calonge, Anunciación A Ilundáin. Ontogeny of Na(+)/L-carnitine transporter and of gamma-trimethylaminobutyraldehyde dehydrogenase and gamma-butyrobetaine hydroxylase genes expression in rat kidney.
Mechanisms of ageing and development.
2009 Apr; 130(4):227-33. doi:
10.1016/j.mad.2008.12.002. [PMID: 19150623] - Reinis Vilskersts, Edgars Liepinsh, Lukasz Mateuszuk, Solveiga Grinberga, Ivars Kalvinsh, Stefan Chlopicki, Maija Dambrova. Mildronate, a regulator of energy metabolism, reduces atherosclerosis in apoE/LDLR-/- mice.
Pharmacology.
2009; 83(5):287-93. doi:
10.1159/000210015. [PMID: 19325254] - 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] - Edgars Liepinsh, Reinis Vilskersts, Elina Skapare, Baiba Svalbe, Janis Kuka, Helena Cirule, Osvalds Pugovics, Ivars Kalvinsh, Maija Dambrova. Mildronate decreases carnitine availability and up-regulates glucose uptake and related gene expression in the mouse heart.
Life sciences.
2008 Oct; 83(17-18):613-9. doi:
10.1016/j.lfs.2008.08.008. [PMID: 18801379] - Maija Dambrova, Helena Cirule, Baiba Svalbe, Liga Zvejniece, Osvalds Pugovichs, Tatjana Zorenko, Ivars Kalvinsh, Edgars Liepinsh, Irina Belozertseva. Effect of inhibiting carnitine biosynthesis on male rat sexual performance.
Physiology & behavior.
2008 Oct; 95(3):341-7. doi:
10.1016/j.physbeh.2008.06.012. [PMID: 18640137] - Sonja Primassin, Frank Ter Veld, Ertan Mayatepek, Ute Spiekerkoetter. Carnitine supplementation induces acylcarnitine production in tissues of very long-chain acyl-CoA dehydrogenase-deficient mice, without replenishing low free carnitine.
Pediatric research.
2008 Jun; 63(6):632-7. doi:
10.1203/pdr.0b013e31816ff6f0. [PMID: 18317232] - Robert Ringseis, Sebastian Luci, Julia Spielmann, Holger Kluge, Maren Fischer, Stefanie Geissler, Gaiping Wen, Frank Hirche, Klaus Eder. Clofibrate treatment up-regulates novel organic cation transporter (OCTN)-2 in tissues of pigs as a model of non-proliferating species.
European journal of pharmacology.
2008 Mar; 583(1):11-7. doi:
10.1016/j.ejphar.2008.01.008. [PMID: 18258227] - 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] - William R Wikoff, Jon A Gangoiti, Bruce A Barshop, Gary Siuzdak. Metabolomics identifies perturbations in human disorders of propionate metabolism.
Clinical chemistry.
2007 Dec; 53(12):2169-76. doi:
10.1373/clinchem.2007.089011. [PMID: 17951291] - E M Sharipova, E V Salna, M I Dzintare, L I Lauberte, N I Sjakste, V S Gordiushina, I I Kalvinsh. [The effect of mildronate and related substances on levels of thyroid hormones and some intermediates of lipid and carbohidrate metabolism in the hyperthyroid and hypothyroid rats].
Biomeditsinskaia khimiia.
2007 Nov; 53(6):672-82. doi:
NULL. [PMID: 18323152] - 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] - Qing-Ri Cao, Shan Ren, Mi-Jin Park, Yun-Jaie Choi, Beom-Jin Lee. Determination of highly soluble L-carnitine in biological samples by reverse phase high performance liquid chromatography with fluorescent derivatization.
Archives of pharmacal research.
2007 Aug; 30(8):1041-6. doi:
10.1007/bf02993974. [PMID: 17879759] - Edgars Liepinsh, Reinis Vilskersts, Dagnija Loca, Olga Kirjanova, Osvalds Pugovichs, Ivars Kalvinsh, Maija Dambrova. Mildronate, an inhibitor of carnitine biosynthesis, induces an increase in gamma-butyrobetaine contents and cardioprotection in isolated rat heart infarction.
Journal of cardiovascular pharmacology.
2006 Dec; 48(6):314-9. doi:
10.1097/01.fjc.0000250077.07702.23. [PMID: 17204911] - Caroline Rigault, Françoise Le Borgne, Jean Demarquoy. Genomic structure, alternative maturation and tissue expression of the human BBOX1 gene.
Biochimica et biophysica acta.
2006 Dec; 1761(12):1469-81. doi:
10.1016/j.bbalip.2006.09.014. [PMID: 17110165] - H H Huidekoper, J Schneider, T Westphal, F M Vaz, M Duran, F A Wijburg. Prolonged moderate-intensity exercise without and with L-carnitine supplementation in patients with MCAD deficiency.
Journal of inherited metabolic disease.
2006 Oct; 29(5):631-6. doi:
10.1007/s10545-006-0355-3. [PMID: 16972171] - Yun-peng Zhao, Xiao-yun Wang, Zhi-can Wang, Yin Lu, Cheng-xin Fu, Shao-yuan Chen. Essential oil of Actinidia macrosperma, a catnip response kiwi endemic to China.
Journal of Zhejiang University. Science. B.
2006 Sep; 7(9):708-12. doi:
10.1631/jzus.2006.b0708. [PMID: 16909471] - Laurence Vernez, Michael Dickenmann, Jürg Steiger, Markus Wenk, Stephan Krähenbühl. Effect of L-carnitine on the kinetics of carnitine, acylcarnitines and butyrobetaine in long-term haemodialysis.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2006 Feb; 21(2):450-8. doi:
10.1093/ndt/gfi257. [PMID: 16286428] - Alessandro Peschechera, Maurizio Scalibastri, Francesco Russo, Mauro Giorgio Giarrizzo, Paolo Carminati, Fabio Giannessi, Arduino Arduini, Rita Ricciolini. Carnitine depletion in rat pups from mothers given mildronate: a model of carnitine deficiency in late fetal and neonatal life.
Life sciences.
2005 Oct; 77(24):3078-91. doi:
10.1016/j.lfs.2005.03.029. [PMID: 15979102] - Laurence Vernez, Markus Wenk, Stephan Krähenbühl. Determination of carnitine and acylcarnitines in plasma by high-performance liquid chromatography/electrospray ionization ion trap tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2004; 18(11):1233-8. doi:
10.1002/rcm.1470. [PMID: 15164354] - Nikolajs Sjakste, Larisa Baumane, Jean-Luc Boucher, Maija Dzintare, Dainuvite Meirena, Jelizaveta Sjakste, Lasma Lauberte, Ivars Kalvinsh. Effects of gamma-butyrobetaine and mildronate on nitric oxide production in lipopolysaccharide-treated rats.
Basic & clinical pharmacology & toxicology.
2004 Jan; 94(1):46-50. doi:
NULL. [PMID: 14725614] - Piyasena Hewawasam, Min Ding, Nathan Chen, Dalton King, Jay Knipe, Lorraine Pajor, Astrid Ortiz, Valentin K Gribkoff, John Starrett. Synthesis of water-soluble prodrugs of BMS-191011: a maxi-K channel opener targeted for post-stroke neuroprotection.
Bioorganic & medicinal chemistry letters.
2003 May; 13(10):1695-8. doi:
10.1016/s0960-894x(03)00296-8. [PMID: 12729644] - 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:
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Cellular and molecular life sciences : CMLS.
2002 Mar; 59(3):540-5. doi:
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The Journal of pharmacy and pharmacology.
2001 Apr; 53(4):527-33. doi:
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European journal of biochemistry.
2001 Mar; 268(6):1876-87. doi:
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Biochimica et biophysica acta.
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Eksperimental'naia i klinicheskaia farmakologiia.
1997 May; 60(3):54-7. doi:
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