Palmitoylcarnitine (BioDeep_00000003254)

Main id: BioDeep_00000641215

Secondary id: BioDeep_00000405221, BioDeep_00001891269

human metabolite blood metabolite LipidSearch natural product


代谢物信息卡片


O-hexadecanoyl-R-carnitine

化学式: C23H45NO4 (399.33484100000004)
中文名称: 棕榈酰左旋肉碱, 棕榈酰-L-肉碱
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 0.1%

分子结构信息

SMILES: CCCCCCCCCCCCCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C
InChI: InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3

描述信息

D018977 - Micronutrients > D014815 - Vitamins
CONFIDENCE standard compound; INTERNAL_ID 250

同义名列表

8 个代谢物同义名

O-hexadecanoyl-R-carnitine; Palmitoyl-L-carnitine; L-Palmitoylcarnitine; PALMITOYLCARNITINE; CAR 16:0; Palmitoylcarnitine; L-Palmitoylcarnitine; Palmitoyl-L-carnitine



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(7)

BioCyc(0)

PlantCyc(0)

代谢反应

120 个相关的代谢反应过程信息。

Reactome(84)

BioCyc(2)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(32)

PharmGKB(0)

21 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

  • Ruirui Dong, Ningzhen Ye, Shaojie Zhao, Gaoying Wang, Yan Zhang, Tiejun Wang, Ping Zou, Jing Wang, Tingting Yao, Minjian Chen, Conghua Zhou, Ting Zhang, Liang Luo. Studies on Novel Diagnostic and Predictive Biomarkers of Intrahepatic Cholestasis of Pregnancy Through Metabolomics and Proteomics. Frontiers in immunology. 2021; 12(?):733225. doi: 10.3389/fimmu.2021.733225. [PMID: 34721396]
  • YueTao Liu, XinQi Li, AiPing Li, Ke Li, XueMei Qin. UHPLC Q-Exactive MS-based spleen metabolomics and lipidomics to explore the effect mechanisms of Danggui Buxue Decoction in anemia mice. Journal of pharmaceutical and biomedical analysis. 2020 Jun; 185(?):113234. doi: 10.1016/j.jpba.2020.113234. [PMID: 32171146]
  • Khalil Mallah, Jusal Quanico, Antonella Raffo-Romero, Tristan Cardon, Soulaimane Aboulouard, David Devos, Firas Kobeissy, Kazem Zibara, Michel Salzet, Isabelle Fournier. Matrix-Assisted Laser Desorption/Ionization-Mass Spectrometry Imaging of Lipids in Experimental Model of Traumatic Brain Injury Detecting Acylcarnitines as Injury Related Markers. Analytical chemistry. 2019 09; 91(18):11879-11887. doi: 10.1021/acs.analchem.9b02633. [PMID: 31412203]
  • Larissa Menezes Dos Reis, Douglas Adamoski, Rodolpho Ornitz Oliveira Souza, Carolline Fernanda Rodrigues Ascenção, Krishina Ratna Sousa de Oliveira, Felipe Corrêa-da-Silva, Fábio Malta de Sá Patroni, Marília Meira Dias, Sílvio Roberto Consonni, Pedro Manoel Mendes de Moraes-Vieira, Ariel Mariano Silber, Sandra Martha Gomes Dias. Dual inhibition of glutaminase and carnitine palmitoyltransferase decreases growth and migration of glutaminase inhibition-resistant triple-negative breast cancer cells. The Journal of biological chemistry. 2019 06; 294(24):9342-9357. doi: 10.1074/jbc.ra119.008180. [PMID: 31040181]
  • Shannon N Mostyn, Tristan Rawling, Sarasa Mohammadi, Susan Shimmon, Zachary J Frangos, Subhodeep Sarker, Arsalan Yousuf, Irina Vetter, Renae M Ryan, Macdonald J Christie, Robert J Vandenberg. Development of an N-Acyl Amino Acid That Selectively Inhibits the Glycine Transporter 2 To Produce Analgesia in a Rat Model of Chronic Pain. Journal of medicinal chemistry. 2019 03; 62(5):2466-2484. doi: 10.1021/acs.jmedchem.8b01775. [PMID: 30714733]
  • Takashi Tsuji, Morio Matsumoto, Masaya Nakamura, Takeshi Miyamoto, Mitsuru Yagi, Nobuyuki Fujita, Eijiro Okada, Narihito Nagoshi, Osahiko Tsuji, Kota Watanabe. Metabolite profiling of plasma in patients with ossification of the posterior longitudinal ligament. Journal of orthopaedic science : official journal of the Japanese Orthopaedic Association. 2018 Nov; 23(6):878-883. doi: 10.1016/j.jos.2018.07.001. [PMID: 30075996]
  • Sree V Chintapalli, Andriy Anishkin, Sean H Adams. Exploring the entry route of palmitic acid and palmitoylcarnitine into myoglobin. Archives of biochemistry and biophysics. 2018 10; 655(?):56-66. doi: 10.1016/j.abb.2018.07.024. [PMID: 30092229]
  • Margot Riggi, Karolina Niewola-Staszkowska, Nicolas Chiaruttini, Adai Colom, Beata Kusmider, Vincent Mercier, Saeideh Soleimanpour, Michael Stahl, Stefan Matile, Aurélien Roux, Robbie Loewith. Decrease in plasma membrane tension triggers PtdIns(4,5)P2 phase separation to inactivate TORC2. Nature cell biology. 2018 09; 20(9):1043-1051. doi: 10.1038/s41556-018-0150-z. [PMID: 30154550]
  • Fatima-Zahra Bouchouirab, Mélanie Fortin, Christophe Noll, Jean Dubé, André C Carpentier. Plasma Palmitoyl-Carnitine (AC16:0) Is a Marker of Increased Postprandial Nonesterified Incomplete Fatty Acid Oxidation Rate in Adults With Type 2 Diabetes. Canadian journal of diabetes. 2018 Aug; 42(4):382-388.e1. doi: 10.1016/j.jcjd.2017.09.002. [PMID: 29129455]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Yuiko Kamei, Daigo Kamei, Ken Tsuchiya, Michio Mineshima, Kosaku Nitta. Association between 4-year all-cause mortality and carnitine profile in maintenance hemodialysis patients. PloS one. 2018; 13(8):e0201591. doi: 10.1371/journal.pone.0201591. [PMID: 30133480]
  • Jie Liu, Gang Zhan, Dewei Chen, Jian Chen, Zhi-Bin Yuan, Er-Long Zhang, Yi-Xing Gao, Gang Xu, Bing-Da Sun, Wenting Liao, Yu-Qi Gao. UPLC‑QTOFMS‑based metabolomic analysis of the serum of hypoxic preconditioning mice. Molecular medicine reports. 2017 Nov; 16(5):6828-6836. doi: 10.3892/mmr.2017.7493. [PMID: 28901489]
  • Maria Chondronikola, Rabia Asghar, Xiaojun Zhang, Edgar L Dillon, William J Durham, Zhanpin Wu, Craig Porter, Maria Camacho-Hughes, Yingxin Zhao, Allan R Brasier, Elena Volpi, Melinda Sheffield-Moore, Nicola Abate, Labros Sidossis, Demidmaa Tuvdendorj. Palmitoyl-carnitine production by blood cells associates with the concentration of circulating acyl-carnitines in healthy overweight women. Clinical nutrition (Edinburgh, Scotland). 2017 10; 36(5):1310-1319. doi: 10.1016/j.clnu.2016.08.019. [PMID: 27624997]
  • Edgars Liepinsh, Marina Makrecka-Kuka, Elina Makarova, Kristine Volska, Karlis Vilks, Eduards Sevostjanovs, Unigunde Antone, Janis Kuka, Reinis Vilskersts, Daina Lola, Einars Loza, Solveiga Grinberga, Maija Dambrova. Acute and long-term administration of palmitoylcarnitine induces muscle-specific insulin resistance in mice. BioFactors (Oxford, England). 2017 Sep; 43(5):718-730. doi: 10.1002/biof.1378. [PMID: 28759135]
  • Paula M Miotto, Gregory R Steinberg, Graham P Holloway. Controlling skeletal muscle CPT-I malonyl-CoA sensitivity: the importance of AMPK-independent regulation of intermediate filaments during exercise. The Biochemical journal. 2017 02; 474(4):557-569. doi: 10.1042/bcj20160913. [PMID: 27941154]
  • Kenji Yamada, Hironori Kobayashi, Ryosuke Bo, Jamiyan Purevsuren, Yuichi Mushimoto, Tomoo Takahashi, Yuki Hasegawa, Takeshi Taketani, Seiji Fukuda, Seiji Yamaguchi. Efficacy of bezafibrate on fibroblasts of glutaric acidemia type II patients evaluated using an in vitro probe acylcarnitine assay. Brain & development. 2017 Jan; 39(1):48-57. doi: 10.1016/j.braindev.2016.08.004. [PMID: 27591119]
  • Gaokun Qiu, Yan Zheng, Hao Wang, Jie Sun, Hongxia Ma, Yang Xiao, Yizhun Li, Yu Yuan, Handong Yang, Xiulou Li, Xinwen Min, Ce Zhang, Chengwei Xu, Yue Jiang, Xiaomin Zhang, Meian He, Ming Yang, Zhibin Hu, Huiru Tang, Hongbing Shen, Frank B Hu, An Pan, Tangchun Wu. Plasma metabolomics identified novel metabolites associated with risk of type 2 diabetes in two prospective cohorts of Chinese adults. International journal of epidemiology. 2016 10; 45(5):1507-1516. doi: 10.1093/ije/dyw221. [PMID: 27694567]
  • Marieke G Schooneman, Gabriella A M Ten Have, Naomi van Vlies, Sander M Houten, Nicolaas E P Deutz, Maarten R Soeters. Transorgan fluxes in a porcine model reveal a central role for liver in acylcarnitine metabolism. American journal of physiology. Endocrinology and metabolism. 2015 Aug; 309(3):E256-64. doi: 10.1152/ajpendo.00503.2014. [PMID: 26037250]
  • Marina Makrecka, Janis Kuka, Kristine Volska, Unigunde Antone, Eduards Sevostjanovs, Helena Cirule, Solveiga Grinberga, Osvalds Pugovics, Maija Dambrova, Edgars Liepinsh. Long-chain acylcarnitine content determines the pattern of energy metabolism in cardiac mitochondria. Molecular and cellular biochemistry. 2014 Oct; 395(1-2):1-10. doi: 10.1007/s11010-014-2106-3. [PMID: 24878991]
  • Yangzhen Shao, Bjorn Redfors, David Benoist, Sigfus Gizurarson, Elmir Omerovic. Lipid metabolites and their differential pro-arrhythmic profiles: of importance in the development of a new anti-arrhythmic pharmacology. Molecular and cellular biochemistry. 2014 Aug; 393(1-2):191-7. doi: 10.1007/s11010-014-2060-0. [PMID: 24771065]
  • Huawei Zhang, Peng Fu, Beilei Ke, Shuping Wang, Min Li, Lin Han, Chengcheng Peng, Weidong Zhang, Runhui Liu. Metabolomic analysis of biochemical changes in the plasma and urine of collagen-induced arthritis in rats after treatment with Huang-Lian-Jie-Du-Tang. Journal of ethnopharmacology. 2014 May; 154(1):55-64. doi: 10.1016/j.jep.2014.03.007. [PMID: 24709313]
  • Réjane Morand, Massimiliano Donzelli, Manuel Haschke, Stephan Krähenbühl. Quantification of plasma carnitine and acylcarnitines by high-performance liquid chromatography-tandem mass spectrometry using online solid-phase extraction. Analytical and bioanalytical chemistry. 2013 Nov; 405(27):8829-36. doi: 10.1007/s00216-013-7309-z. [PMID: 23995505]
  • Thor Ueland, Asbjørn Svardal, Erik Øie, Erik T Askevold, Ståle H Nymoen, Bodil Bjørndal, Christen P Dahl, Lars Gullestad, Rolf K Berge, Pål Aukrust. Disturbed carnitine regulation in chronic heart failure--increased plasma levels of palmitoyl-carnitine are associated with poor prognosis. International journal of cardiology. 2013 Sep; 167(5):1892-9. doi: 10.1016/j.ijcard.2012.04.150. [PMID: 22622056]
  • Jill A Kanaley, Samyah Shadid, Michael T Sheehan, ZengKui Guo, Michael D Jensen. Hyperinsulinemia and skeletal muscle fatty acid trafficking. American journal of physiology. Endocrinology and metabolism. 2013 Aug; 305(4):E540-8. doi: 10.1152/ajpendo.00143.2013. [PMID: 23820622]
  • Karolina Tułodziecka, Magdalena Czeredys, Katarzyna A Nałęcz. Palmitoylcarnitine affects localization of growth associated protein GAP-43 in plasma membrane subdomains and its interaction with Gα(o) in neuroblastoma NB-2a cells. Neurochemical research. 2013 Mar; 38(3):519-29. doi: 10.1007/s11064-012-0944-5. [PMID: 23224819]
  • Karen Dixen, Astrid L Basse, Maria Murholm, Marie S Isidor, Lillian H L Hansen, M Christine H Petersen, Lise Madsen, Natasa Petrovic, Jan Nedergaard, Bjørn Quistorff, Jacob B Hansen. ERRγ enhances UCP1 expression and fatty acid oxidation in brown adipocytes. Obesity (Silver Spring, Md.). 2013 Mar; 21(3):516-24. doi: 10.1002/oby.20067. [PMID: 23404793]
  • Ulrikke Voss, Elin Sand, Björn Olde, Eva Ekblad. Enteric neuropathy can be induced by high fat diet in vivo and palmitic acid exposure in vitro. PloS one. 2013; 8(12):e81413. doi: 10.1371/journal.pone.0081413. [PMID: 24312551]
  • Xiaolei Shi, Dan Yao, Blake A Gosnell, Chi Chen. Lipidomic profiling reveals protective function of fatty acid oxidation in cocaine-induced hepatotoxicity. Journal of lipid research. 2012 Nov; 53(11):2318-30. doi: 10.1194/jlr.m027656. [PMID: 22904346]
  • Wenche Jørgensen, Peter Jelnes, Kasper A Rud, Lillian L Hansen, Niels Grunnet, Bjørn Quistorff. Progression of type 2 diabetes in GK rats affects muscle and liver mitochondria differently: pronounced reduction of complex II flux is observed in liver only. American journal of physiology. Endocrinology and metabolism. 2012 Aug; 303(4):E515-23. doi: 10.1152/ajpendo.00103.2012. [PMID: 22713504]
  • Xiao-Jun Zhang, Noe A Rodriguez, Lijian Wang, Demidmaa Tuvdendorj, Zhanpin Wu, Alai Tan, David N Herndon, Robert R Wolfe. Measurement of precursor enrichment for calculating intramuscular triglyceride fractional synthetic rate. Journal of lipid research. 2012 Jan; 53(1):119-25. doi: 10.1194/jlr.m019901. [PMID: 21934122]
  • Xudong Wang, Gail J Mick, Edmund Maser, Kenneth McCormick. Manifold effects of palmitoylcarnitine on endoplasmic reticulum metabolism: 11β-hydroxysteroid dehydrogenase 1, flux through hexose-6-phosphate dehydrogenase and NADPH concentration. The Biochemical journal. 2011 Jul; 437(1):109-15. doi: 10.1042/bj20102069. [PMID: 21492096]
  • Nolwenn Brandhonneur, Gilles Dollo, Maja Ratajczak-Enselme, Anne Laure Deniau, François Chevanne, Jean Pierre Estèbe, Alain Legrand, Pascal Le Corre. Ex vivo and in vivo diffusion of ropivacaine through spinal meninges: influence of absorption enhancers. International journal of pharmaceutics. 2011 Feb; 404(1-2):36-41. doi: 10.1016/j.ijpharm.2010.10.049. [PMID: 21056096]
  • Nobuyuki Doi, Mikio Tomita, Masahiro Hayashi. Absorption enhancement effect of acylcarnitines through changes in tight junction protein in Caco-2 cell monolayers. Drug metabolism and pharmacokinetics. 2011; 26(2):162-70. doi: 10.2133/dmpk.dmpk-10-rg-071. [PMID: 21206134]
  • Jean-Paul Bonnefont, Jean Bastin, Anthony Behin, Fatima Djouadi. Bezafibrate for an inborn mitochondrial beta-oxidation defect. The New England journal of medicine. 2009 Feb; 360(8):838-40. doi: 10.1056/nejmc0806334. [PMID: 19228633]
  • Zhi Liu, Abdul E Mutlib, Jianyao Wang, Rasmy E Talaat. Liquid chromatography/mass spectrometry determination of endogenous plasma acetyl and palmitoyl carnitines as potential biomarkers of beta-oxidation in mice. Rapid communications in mass spectrometry : RCM. 2008 Nov; 22(21):3434-42. doi: 10.1002/rcm.3755. [PMID: 18837479]
  • Muhammad A Abdul-Ghani, Florian L Muller, Yuhong Liu, Alberto O Chavez, Bogdan Balas, Pengou Zuo, Zhi Chang, Devjit Tripathy, Rucha Jani, Marjorie Molina-Carrion, Adriana Monroy, Franco Folli, Holly Van Remmen, Ralph A DeFronzo. Deleterious action of FA metabolites on ATP synthesis: possible link between lipotoxicity, mitochondrial dysfunction, and insulin resistance. American journal of physiology. Endocrinology and metabolism. 2008 Sep; 295(3):E678-85. doi: 10.1152/ajpendo.90287.2008. [PMID: 18593850]
  • John J Lehman, Sihem Boudina, Natasha Hausler Banke, Nandakumar Sambandam, Xianlin Han, Deanna M Young, Teresa C Leone, Richard W Gross, E Douglas Lewandowski, E Dale Abel, Daniel P Kelly. The transcriptional coactivator PGC-1alpha is essential for maximal and efficient cardiac mitochondrial fatty acid oxidation and lipid homeostasis. American journal of physiology. Heart and circulatory physiology. 2008 Jul; 295(1):H185-96. doi: 10.1152/ajpheart.00081.2008. [PMID: 18487436]
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  • 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]
  • Timothy K Tippin, Dhiren R Thakker. Biorelevant refinement of the Caco-2 cell culture model to assess efficacy of paracellular permeability enhancers. Journal of pharmaceutical sciences. 2008 May; 97(5):1977-92. doi: 10.1002/jps.21118. [PMID: 17724658]
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