Lignoceric acid (C24) (BioDeep_00000002668)

 

Secondary id: BioDeep_00000400368, BioDeep_00000859848

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


Tetracosanoic acid

化学式: C24H48O2 (368.3654108)
中文名称: 木焦油酸, 木蜡酸, 二十四烷酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.09%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

Lignoceric acid (C24). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/lignoceric_acid_(c24) (retrieved 2024-11-10) (BioDeep RN: BioDeep_00000002668). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(=O)(O)CCCCCCCCCCCCCCCCCCCCCCC
InChI: InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)

描述信息

Lignoceric acid, also known as N-tetracosanoic acid or tetraeicosanoate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, lignoceric acid is considered to be a fatty acid lipid molecule. Lignoceric acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Lignoceric acid can be found in a number of food items such as hazelnut, cheese, rye bread, and cetacea (dolphin, porpoise, whale), which makes lignoceric acid a potential biomarker for the consumption of these food products. Lignoceric acid can be found primarily in blood and feces, as well as in human fibroblasts tissue. Lignoceric acid exists in all eukaryotes, ranging from yeast to humans. In humans, lignoceric acid is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Lignoceric acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoceric acid (1.1\\\\% – 2.2\\\\%). This fatty acid is also a byproduct of lignin production .
Tetracosanoic acid is a C24 straight-chain saturated fatty acid. It has a role as a volatile oil component, a plant metabolite, a human metabolite and a Daphnia tenebrosa metabolite. It is a very long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetracosanoate. Tetracosanoic acid, also known as N-tetracosanoate or lignoceric acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tetracosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tetracosanoic acid is a potentially toxic compound.
Acquisition and generation of the data is financially supported in part by CREST/JST.
Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid, which is synthesized in the developing brain. Lignoceric acid is also a by-product of lignin production. Lignoceric acid can be used for Zellweger cerebro‐hepato‐renal syndrome and adrenoleukodystrophy research[1][2].
Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid, which is synthesized in the developing brain. Lignoceric acid is also a by-product of lignin production. Lignoceric acid can be used for Zellweger cerebro‐hepato‐renal syndrome and adrenoleukodystrophy research[1][2].

同义名列表

27 个代谢物同义名

Tetracosanoic acid, potassium salt (1:1); Lignoceric acid, silver (1+) salt; Lignoceric acid, potassium salt; Lignoceric acid, sodium salt; Potassium tetracosanoate; N-Tetracosanoic acid; Tetraeicosanoic acid; Tetraicosanoic acid; Tetracosanoic acid; Tetracosanic acid; Tetracosoic acid; N-Tetracosanoate; Tetracosansaeure; CH3-[CH2]22-COOH; Tetraeicosanoate; Lignozerinsaeure; Lignoceric acid; Tetraicosanoate; tetracosanoate; Carnaubic acid; Tetracosanate; Tetracosoate; Lignocerate; FA(24:0); FA 24:0; C24:0; Lignoceric Acid



数据库引用编号

23 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

14 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(12)

PharmGKB(0)

114 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

  • Yudai Yamashita, Takayuki Narita, Yushi Oishi. Non-Equilibrium Phase-Separated State of(Palmitic Acid/Lignoceric Acid) Mixed Monolayer. Journal of oleo science. 2020 Jun; 69(6):569-572. doi: 10.5650/jos.ess20038. [PMID: 32404553]
  • Danni Li, Jeffrey R Misialek, Ma Jing, Michael Y Tsai, John H Eckfeldt, Lyn M Steffen, David Knopman, Lisa Wruck, Rebecca Gottesman, Tom H Mosley, A Richey Sharrett, Alvaro Alonso. Plasma phospholipid very-long-chain SFAs in midlife and 20-year cognitive change in the Atherosclerosis Risk in Communities (ARIC): a cohort study. The American journal of clinical nutrition. 2020 06; 111(6):1252-1258. doi: 10.1093/ajcn/nqaa048. [PMID: 32320012]
  • Anna Petroni, Rita Paroni, Anna Maria Aloisi, Milena Blasevich, Nabil Haman, Dimitrios Fessas. Thermogenic flux induced by lignoceric acid in peroxisomes isolated from HepG2 cells and from X-adrenoleukodystrophy and control fibroblasts. Journal of cellular physiology. 2019 08; 234(10):18344-18348. doi: 10.1002/jcp.28467. [PMID: 30932193]
  • Rozenn N Lemaitre, Paul N Jensen, Andrew Hoofnagle, Barbara McKnight, Amanda M Fretts, Irena B King, David S Siscovick, Bruce M Psaty, Susan R Heckbert, Dariush Mozaffarian, Nona Sotoodehnia. Plasma Ceramides and Sphingomyelins in Relation to Heart Failure Risk. Circulation. Heart failure. 2019 07; 12(7):e005708. doi: 10.1161/circheartfailure.118.005708. [PMID: 31296099]
  • Atsushi Henmi, Minori Shoji, Masato Nomura, Toshio Inoue. Fatty Acid Composition and Applications of Eriobotrya japonica Seed Oil. Journal of oleo science. 2019 Jul; 68(7):599-606. doi: 10.5650/jos.ess18178. [PMID: 31178459]
  • Anna Sofia Tascini, Massimo G Noro, John M Seddon, Rongjun Chen, Fernando Bresme. Mechanisms of lipid extraction from skin lipid bilayers by sebum triglycerides. Physical chemistry chemical physics : PCCP. 2019 Jan; 21(3):1471-1477. doi: 10.1039/c8cp05706k. [PMID: 30607404]
  • Maren Podewitz, Yin Wang, Paraskevi Gkeka, Susanne von Grafenstein, Klaus R Liedl, Zoe Cournia. Phase Diagram of a Stratum Corneum Lipid Mixture. The journal of physical chemistry. B. 2018 11; 122(46):10505-10521. doi: 10.1021/acs.jpcb.8b07200. [PMID: 30351111]
  • Rozenn N Lemaitre, Barbara McKnight, Nona Sotoodehnia, Amanda M Fretts, Waqas T Qureshi, Xiaoling Song, Irena B King, Colleen M Sitlani, David S Siscovick, Bruce M Psaty, Dariush Mozaffarian. Circulating Very Long-Chain Saturated Fatty Acids and Heart Failure: The Cardiovascular Health Study. Journal of the American Heart Association. 2018 11; 7(21):e010019. doi: 10.1161/jaha.118.010019. [PMID: 30608197]
  • Maryem Bezine, Sonia Maatoug, Rym Ben Khalifa, Meryam Debbabi, Amira Zarrouk, Yuqin Wang, William J Griffiths, Thomas Nury, Mohammad Samadi, Anne Vejux, Jérôme de Sèze, Thibault Moreau, Riadh Kharrat, Mohamed El Ayeb, Gérard Lizard. Modulation of Kv3.1b potassium channel level and intracellular potassium concentration in 158N murine oligodendrocytes and BV-2 murine microglial cells treated with 7-ketocholesterol, 24S-hydroxycholesterol or tetracosanoic acid (C24:0). Biochimie. 2018 Oct; 153(?):56-69. doi: 10.1016/j.biochi.2018.02.008. [PMID: 29462682]
  • Maryem Bezine, Meryam Debbabi, Thomas Nury, Rym Ben-Khalifa, Mohammad Samadi, Mustapha Cherkaoui-Malki, Anne Vejux, Quentin Raas, Jérôme de Sèze, Thibault Moreau, Mohamed El-Ayeb, Gérard Lizard. Evidence of K+ homeostasis disruption in cellular dysfunction triggered by 7-ketocholesterol, 24S-hydroxycholesterol, and tetracosanoic acid (C24:0) in 158N murine oligodendrocytes. Chemistry and physics of lipids. 2017 10; 207(Pt B):135-150. doi: 10.1016/j.chemphyslip.2017.03.006. [PMID: 28322741]
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  • Enamul H Mojumdar, Gert S Gooris, David J Barlow, M Jayne Lawrence, Bruno Deme, Joke A Bouwstra. Skin lipids: localization of ceramide and fatty acid in the unit cell of the long periodicity phase. Biophysical journal. 2015 Jun; 108(11):2670-9. doi: 10.1016/j.bpj.2015.04.030. [PMID: 26039168]
  • Seshadri Shivashankar, Manoharan Sumathi. Do seed VLCFAs trigger spongy tissue formation in Alphonso mango by inducing germination?. Journal of biosciences. 2015 Jun; 40(2):375-87. doi: 10.1007/s12038-015-9515-7. [PMID: 25963264]
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  • Fahmi Nasrallah, Ichraf Kraoua, Wiem Zidi, Souheil Omar, Haifa Sanhaji, Moncef Feki, Ilhem Turki Ben Youssef, Naziha Kaabachi. X-linked Adrenoleukodystrophy, The Tunisian Experience. Clinical laboratory. 2015; 61(10):1531-6. doi: 10.7754/clin.lab.2015.150318. [PMID: 26642716]
  • Barbora Školová, Klára Hudská, Petra Pullmannová, Andrej Kováčik, Karel Palát, Jaroslav Roh, Jana Fleddermann, Irina Estrela-Lopis, Kateřina Vávrová. Different phase behavior and packing of ceramides with long (C16) and very long (C24) acyls in model membranes: infrared spectroscopy using deuterated lipids. The journal of physical chemistry. B. 2014 Sep; 118(35):10460-70. doi: 10.1021/jp506407r. [PMID: 25122563]
  • Bruna Renata Casadei, Patrícia De Oliveira Carvalho, Karin A Riske, Raquel De Melo Barbosa, Eneida De Paula, Cleyton Crepaldi Domingues. Brij detergents reveal new aspects of membrane microdomain in erythrocytes. Molecular membrane biology. 2014 Sep; 31(6):195-205. doi: 10.3109/09687688.2014.949319. [PMID: 25222860]
  • Masashi Oguri, Gert S Gooris, Kotatsu Bito, Joke A Bouwstra. The effect of the chain length distribution of free fatty acids on the mixing properties of stratum corneum model membranes. Biochimica et biophysica acta. 2014 Jul; 1838(7):1851-61. doi: 10.1016/j.bbamem.2014.02.009. [PMID: 24565794]
  • Amanda M Fretts, Dariush Mozaffarian, David S Siscovick, Luc Djousse, Susan R Heckbert, Irena B King, Barbara McKnight, Colleen Sitlani, Frank M Sacks, Xiaoling Song, Nona Sotoodehnia, Donna Spiegelman, Erin R Wallace, Rozenn N Lemaitre. Plasma phospholipid saturated fatty acids and incident atrial fibrillation: the Cardiovascular Health Study. Journal of the American Heart Association. 2014 Jun; 3(3):e000889. doi: 10.1161/jaha.114.000889. [PMID: 24970268]
  • Yuya Yamazaki, Kazuya Kondo, Ryouta Maeba, Megumi Nishimukai, Toru Nezu, Hiroshi Hara. Proportion of nervonic acid in serum lipids is associated with serum plasmalogen levels and metabolic syndrome. Journal of oleo science. 2014; 63(5):527-37. doi: 10.5650/jos.ess13226. [PMID: 24770479]
  • Dong Chang, Shengzhong Rong, Yannan Zhang, Qian Sha, Meihua Liang, Xuefei Zhang, Miaojing Li, Hongzhi Pan. Serum free fatty acids level in senile cataract. Journal of the American College of Nutrition. 2014; 33(5):406-11. doi: 10.1080/07315724.2013.875420. [PMID: 25079310]
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