DL-Acetylcarnitine (BioDeep_00000170090)

Main id: BioDeep_00000018395

 

human metabolite PANOMIX_OTCML-2023 Chemicals and Drugs BioNovoGene_Lab2019


代谢物信息卡片


3-(Acetyloxy)-4-(trimethylammonio)butanoic acid

化学式: C9H17NO4 (203.1157522)
中文名称: 乙酰基左旋肉碱, 乙酰基肉碱, 乙酰肉碱, 乙酰肉碱, 乙酰肉碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 42.19%

分子结构信息

SMILES: CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C
InChI: InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3

描述信息

DL-Acetylcarnitine is an acylcarnitine. More specifically, it is an acetic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review [Dambrova et al. 2021, Physiological Reviews], acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. DL-Acetylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine DL-Acetylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. In particular DL-Acetylcarnitine is elevated in the blood or plasma of individuals with very long chain acyl-CoA dehydrogenase deficiency (PMID: 9034211), colorectal cancer (PMID: 25105552), short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (PMID: 11489939), paclitaxel induced neuropathy (PMID: 29946863), type 2 diabetes Mellitus (PMID: 28726959; PMID: 25964024, PMID: 28726959, PMID: 19369366, PMID: 24358186), chronic heart failure (PMID: 22622056), ornithine transcarbamylase (PMID: 3346778), pre-diabetes (PMID: 23010998, PMID: 24358186), type 1 diabetes mellitus (PMID: 16789638), methylmalonic acidemia (PMID: 8214594), myeloma (PMID: 30096165), and diastolic heart failure (PMID: 26010610). It is also decreased in the blood or plasma of individuals with 3-methyl-crotonyl-glycinuria (PMID: 25732994), antiviral drug induced neuropathy (PMID: 9030365, PMID: 11364244), Alzheimer Disease (PMID: 27196316), major depressive disorder (PMID: 30061399), carnitine palmitoyltransferase 2 deficiency (PMID: 20543534), Familial Mediterranean Fever (PMID: 29900937), chronic fatigue syndrome (PMID: 9854142), methylmalonic acidemia (PMID: 15164354), hepatocellular carcinoma (PMID: 26976432, PMID: 31662827), and coronary artery disease (PMID: 20173117). DL-Acetylcarnitine is elevated in the urine of individuals with colorectal cancer (25105552), uterine fibroids (32590215), heart failure (8070147), diabetes mellitus (10221661), and hepatocellular carcinoma (24923488). It is also decreased in the urine of individuals with carnitine palmitoyltransferase 2 deficiency (20543534). Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulins inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903). In healthy subjects, incre...
An acetic acid ester of carnitine that facilitates movement of acetyl CoA into the matrices of mammalian mitochondria during the oxidation of fatty acids. In addition to his metabolic role, acetyl-L-carnitine (ALC) posses unique neuroprotective, neuromodulatory, and neurotrophic properties this may play an important role in counteracting various disease processes. (PubMed ID 15363640) [HMDB]
N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics
D002491 - Central Nervous System Agents > D018697 - Nootropic Agents
D018977 - Micronutrients > D014815 - Vitamins

同义名列表

32 个代谢物同义名

3-(Acetyloxy)-4-(trimethylammonio)butanoic acid; 3-(acetyloxy)-4-(trimethylazaniumyl)butanoate; 3-(Acetyloxy)-4-(trimethylammonio)butanoate; Sigma-tau brand OF acetyl L-carnitine; Sigma tau brand OF acetyl L carnitine; Glaxo brand OF acetyl L-carnitine; Glaxo brand OF acetyl L carnitine; Acetylcarnitine, (R)-isomer; L-Carnitine acetyl ester; Acetyl-L-(-)-carnitine; Levocarnitine acetyl; (+-)-Acetylcarnitine; O-Acetyl-L-carnitine; DL-O-Acetylcarnitine; L-O-Acetylcarnitine; (-)-Acetylcarnitine; Acetyl-DL-carnitine; (R)-Acetylcarnitine; Acetyl-L-carnitine; Acetyl L carnitine; DL-Acetylcarnitine; Carnitine, acetyl; O-Acetylcarnitine; L-Acetylcarnitine; Acetyl-carnitine; Acetyllcarnitine; Acetyl carnitine; Acetylcarnitine; Branigen; Nicetile; Medosan; Alcar



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

18 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(18)

PharmGKB(0)

7 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

  • Jennifer K Frediani, Asim A Lal, Esther Kim, Sharon L Leslie, David W Boorman, Vinita Singh. The role of diet and non-pharmacologic supplements in the treatment of chronic neuropathic pain: A systematic review. Pain practice : the official journal of World Institute of Pain. 2023 Aug; ?(?):. doi: 10.1111/papr.13291. [PMID: 37654090]
  • Hyo-Suk Ahn, Eun Young Cho, Keun-Sang Yum. Efficacy of γ-linolenic acid, Vitis vinifera extract, and acetyl-L-carnitine combination therapy for improving arterial stiffness in Korean adults: Real-world evidence. Journal of clinical hypertension (Greenwich, Conn.). 2023 Aug; ?(?):. doi: 10.1111/jch.14708. [PMID: 37608640]
  • Xu-Dong Jiang, Yu Liu, Jian-Fei Wu, San-Ni Gong, Yao Ma, Xiang-Dong Zi. Regulation of proliferation, apoptosis, hormone secretion and gene expression by acetyl-L-carnitine in yak (Bos grunniens) granulosa cells. Theriogenology. 2023 Jun; 203(?):61-68. doi: 10.1016/j.theriogenology.2023.03.016. [PMID: 36972666]
  • Yongan Tan, Liubin Xiao, Jing Zhao, Jieyu Zhang, Sheraz Ahmad, Dejin Xu, Guangchun Xu, Linquan Ge. Adenosine Monophosphate-Activated Protein Kinase (AMPK) Phosphorylation Is Required for 20-Hydroxyecdysone Regulates Ecdysis in Apolygus lucorum. International journal of molecular sciences. 2023 May; 24(10):. doi: 10.3390/ijms24108587. [PMID: 37239932]
  • Luke T Izzo, Sophie Trefely, Christina Demetriadou, Jack M Drummond, Takuya Mizukami, Nina Kuprasertkul, Aimee T Farria, Phuong T T Nguyen, Nivitha Murali, Lauren Reich, Daniel S Kantner, Joshua Shaffer, Hayley Affronti, Alessandro Carrer, Andrew Andrews, Brian C Capell, Nathaniel W Snyder, Kathryn E Wellen. Acetylcarnitine shuttling links mitochondrial metabolism to histone acetylation and lipogenesis. Science advances. 2023 May; 9(18):eadf0115. doi: 10.1126/sciadv.adf0115. [PMID: 37134161]
  • Jake Hsu, Nina Fatuzzo, Nielson Weng, Wojciech Michno, Wentao Dong, Maryline Kienle, Yuqin Dai, Anca Pasca, Monther Abu-Remaileh, Natalie Rasgon, Benedetta Bigio, Carla Nasca, Chaitan Khosla. Carnitine octanoyltransferase is important for the assimilation of exogenous acetyl-L-carnitine into acetyl-CoA in mammalian cells. The Journal of biological chemistry. 2023 02; 299(2):102848. doi: 10.1016/j.jbc.2022.102848. [PMID: 36587768]
  • Haoya Yao, Yaoqing Wang, Xiao Zhang, Ping Li, Lin Shang, Xiaocui Chen, Jia Zeng. Targeting peroxisomal fatty acid oxidation improves hepatic steatosis and insulin resistance in obese mice. The Journal of biological chemistry. 2023 02; 299(2):102845. doi: 10.1016/j.jbc.2022.102845. [PMID: 36586435]
  • Yvo J M Op den Kamp, Anne Gemmink, Marlies de Ligt, Bas Dautzenberg, Esther Kornips, Johanna A Jorgensen, Gert Schaart, Russell Esterline, Diego A Pava, Joris Hoeks, Vera B Schrauwen-Hinderling, Sander Kersten, Bas Havekes, Timothy R Koves, Deborah M Muoio, Matthijs K C Hesselink, Jan Oscarsson, Esther Phielix, Patrick Schrauwen. Effects of SGLT2 inhibitor dapagliflozin in patients with type 2 diabetes on skeletal muscle cellular metabolism. Molecular metabolism. 2022 12; 66(?):101620. doi: 10.1016/j.molmet.2022.101620. [PMID: 36280113]
  • Jonathan D Reiss, Alan L Chang, Jonathan A Mayo, Katherine Bianco, Henry C Lee, David K Stevenson, Gary M Shaw, Nima Aghaeepour, Karl G Sylvester. Newborn screen metabolic panels reflect the impact of common disorders of pregnancy. Pediatric research. 2022 08; 92(2):490-497. doi: 10.1038/s41390-021-01753-7. [PMID: 34671094]
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  • Z Naureen, A Dautaj, S Nodari, F Fioretti, K Dhuli, K Anpilogov, L Lorusso, S Paolacci, S Michelini, T Guda, M Kallazi, M Bertelli. Proposal of a food supplement for the management of post-COVID syndrome. European review for medical and pharmacological sciences. 2021 12; 25(1 Suppl):67-73. doi: 10.26355/eurrev_202112_27335. [PMID: 34890036]
  • Quentin L Sciascia, Cornelia Prehn, Jerzy Adamski, Gürbüz Daş, Iris S Lang, Winfried Otten, Solvig Görs, Cornelia C Metges. The Effect of Dietary Protein Imbalance during Pregnancy on the Growth, Metabolism and Circulatory Metabolome of Neonatal and Weaned Juvenile Porcine Offspring. Nutrients. 2021 Sep; 13(9):. doi: 10.3390/nu13093286. [PMID: 34579160]
  • Saman Tauqir, Momina Israr, Bushra Rauf, Muhammad Omar Malik, Syed Hamid Habib, Fawad Ali Shah, Muhammad Usman, Muhammad Asif Raza, Inayat Shah, Haroon Badshah, Ehtesham Ehtesham, Mohsin Shah. Acetyl-L-Carnitine Ameliorates Metabolic and Endocrine Alterations in Women with PCOS: A Double-Blind Randomized Clinical Trial. Advances in therapy. 2021 07; 38(7):3842-3856. doi: 10.1007/s12325-021-01789-5. [PMID: 34047916]
  • Hui Li, Yan Wang, Shizhao Ma, Chaoqun Zhang, Hua Liu, Dianxing Sun. Clinical significance of small molecule metabolites in the blood of patients with different types of liver injury. Scientific reports. 2021 06; 11(1):11642. doi: 10.1038/s41598-021-91164-9. [PMID: 34079030]
  • Suo Decheng, Fan Xia, Wei Shulin, Li Yang. Analysis of Choline, Carnitine, Acetylcarnitine and Acetylcholine in Animal Feeds, Blood and Urine Using Ion Chromatography Coupled with Tandem Mass Spectrometry. Journal of chromatographic science. 2021 Apr; 59(5):405-411. doi: 10.1093/chromsci/bmab011. [PMID: 33618354]
  • Muhammad Zubair Israr, Dennis Bernieh, Andrea Salzano, Shabana Cassambai, Yoshiyuki Yazaki, Liam M Heaney, Donald J L Jones, Leong L Ng, Toru Suzuki. Association of gut-related metabolites with outcome in acute heart failure. American heart journal. 2021 04; 234(?):71-80. doi: 10.1016/j.ahj.2021.01.006. [PMID: 33454370]
  • Guangzhu Wei, Zhongbao Zhou, Yuanshan Cui, Yongjin Huang, Zijin Wan, Xuanyan Che, Yumeng Chai, Yong Zhang. A Meta-Analysis of the Efficacy of L-Carnitine/L-Acetyl-Carnitine or N-Acetyl-Cysteine in Men With Idiopathic Asthenozoospermia. American journal of men's health. 2021 Mar; 15(2):15579883211011371. doi: 10.1177/15579883211011371. [PMID: 33906513]
  • Li-Juan Nie, Jun Liang, Feng Shan, Ya-Yun Xu, Chun-Yu Yan, Xuan Zhou, Zhuo-Yu Cheng, Qing-Rong Xia. A UPLC-MS/MS method for determination of endogenous l-carnitine and acetyl-l-carnitine in serum of patients with depression. Biomedical chromatography : BMC. 2021 Mar; 35(3):e4991. doi: 10.1002/bmc.4991. [PMID: 33119931]
  • Sakshi Dhir, Zaira Khalid, Jisselly Salcedo, Alaa Shanbour. Acetyl-l-Carnitine and New-Onset Psychosis During the COVID-19 Pandemic. The primary care companion for CNS disorders. 2020 12; 22(6):. doi: 10.4088/pcc.20l02804. [PMID: 33271642]
  • Arash Abdolmaleki, Mohammad-Bagher Ghayour, Morteza Behnam-Rassouli. Protective effects of acetyl-L-carnitine against serum and glucose deprivation-induced apoptosis in rat adipose-derived mesenchymal stem cells. Cell and tissue banking. 2020 Dec; 21(4):655-666. doi: 10.1007/s10561-020-09844-1. [PMID: 32564258]
  • Elizabeth K Neumann, Lukasz G Migas, Jamie L Allen, Richard M Caprioli, Raf Van de Plas, Jeffrey M Spraggins. Spatial Metabolomics of the Human Kidney using MALDI Trapped Ion Mobility Imaging Mass Spectrometry. Analytical chemistry. 2020 10; 92(19):13084-13091. doi: 10.1021/acs.analchem.0c02051. [PMID: 32668145]
  • Piotr Tomasz Protas, Alina Kępka, Agnieszka Rybi-Szuminska, Justyna Storonowicz, Mark Klukowski, Anna Wasilewska. Are low birth weight children predisposed to renal loss of carnitine?. The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians. 2020 Aug; 33(15):2612-2617. doi: 10.1080/14767058.2018.1555813. [PMID: 30513037]
  • Carlijn M E Remie, Kay H M Roumans, Michiel P B Moonen, Niels J Connell, Bas Havekes, Julian Mevenkamp, Lucas Lindeboom, Vera H W de Wit, Tineke van de Weijer, Suzanne A B M Aarts, Esther Lutgens, Bauke V Schomakers, Hyung L Elfrink, Rubén Zapata-Pérez, Riekelt H Houtkooper, Johan Auwerx, Joris Hoeks, Vera B Schrauwen-Hinderling, Esther Phielix, Patrick Schrauwen. Nicotinamide riboside supplementation alters body composition and skeletal muscle acetylcarnitine concentrations in healthy obese humans. The American journal of clinical nutrition. 2020 08; 112(2):413-426. doi: 10.1093/ajcn/nqaa072. [PMID: 32320006]
  • Radka Klepochová, Michael Leutner, Magdalena Bastian, Michael Krebs, Michael Weber, Siegfried Trattnig, Alexandra Kautzky-Willer, Martin Krššák. Muscle-Specific Relation of Acetylcarnitine and Intramyocellular Lipids to Chronic Hyperglycemia: A Pilot 3-T 1H MRS Study. Obesity (Silver Spring, Md.). 2020 08; 28(8):1405-1411. doi: 10.1002/oby.22846. [PMID: 32820618]
  • Nanxiang Xiong, Xiaofei Gao, Hongyang Zhao, Feng Cai, Fang-Cheng Zhang, Ye Yuan, Weichao Liu, Fangping He, Lauren G Zacharias, Hong Lin, Hieu S Vu, Chao Xing, Dong-Xiao Yao, Fei Chen, Benyan Luo, Wenzhi Sun, Ralph J DeBerardinis, Hao Xu, Woo-Ping Ge. Using arterial-venous analysis to characterize cancer metabolic consumption in patients. Nature communications. 2020 06; 11(1):3169. doi: 10.1038/s41467-020-16810-8. [PMID: 32576825]
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  • Shixun Wang, Jingtao Xu, Jiahui Zheng, Xincai Zhang, Jingbo Shao, Luyan Zhao, Junqiang Hao. Anti-Inflammatory and Antioxidant Effects of Acetyl-L-Carnitine on Atherosclerotic Rats. Medical science monitor : international medical journal of experimental and clinical research. 2020 Jan; 26(?):e920250. doi: 10.12659/msm.920250. [PMID: 31945029]
  • Antoine Cherix, Thomas Larrieu, Jocelyn Grosse, João Rodrigues, Bruce McEwen, Carla Nasca, Rolf Gruetter, Carmen Sandi. Metabolic signature in nucleus accumbens for anti-depressant-like effects of acetyl-L-carnitine. eLife. 2020 01; 9(?):. doi: 10.7554/elife.50631. [PMID: 31922486]
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