Nervonic acid (BioDeep_00000000517)

 

Secondary id: BioDeep_00000393881

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


NERVONIC ACID (CONSTITUENT OF BORAGE SEED OIL)

化学式: C24H46O2 (366.34976159999997)
中文名称: 二十四碳烯酸, 神经酸, 神经酸
谱图信息: 最多检出来源 Homo sapiens(blood) 4.38%

分子结构信息

SMILES: C(CCCCCCCCCCC(=O)O)CC/C=C\CCCCCCCC
InChI: InChI=1S/C24H46O2/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/h9-10H,2-8,11-23H2,1H3,(H,25,26)/b10-9-

描述信息

Nervonic acid is a long chain unsaturated fatty acid that is enriched in sphingomyelin. It consists of choline, sphingosine, phosphoric acid, and fatty acid. Nervonic acid may enhance the brain functions and prevent demyelination (Chemical Land21). Research shows that there is negative relationship between nervonic acid and obesity-related risk factors (PMID:16394593). Demyelination in adrenoleukodystrophy (ALD) is associated with an accumulation of very long chain saturated fatty acids stemming from a genetic defect in the peroxisomal beta oxidation system responsible for the chain shortening of these fatty acids. Sphingolipids from post mortem ALD brain have decreased levels of nervonic acid, 24:1(n-9), and increased levels of stearic acid, 18:0. (PMID:8072429).
(15Z)-tetracosenoic acid is a tetracosenoic acid having a cis-double bond at position 15. It is a conjugate acid of a (15Z)-tetracosenoate.
Nervonic acid is a natural product found in Tropaeolum speciosum, Calophyllum inophyllum, and other organisms with data available.
Nervonic Acid is a monounsaturated fatty acid with a 24-carbon backbone and the sole double bond originating from the 9th carbon from the methyl end, with this bond in the cis- configuration.
See also: Borage Seed Oil (part of).
A tetracosenoic acid having a cis-double bond at position 15.
Present in fish and rape seed oils
Nervonic acid is a monounsaturated fatty acid important in the biosynthesis of myelin.
Nervonic acid is a monounsaturated fatty acid important in the biosynthesis of myelin.

同义名列表

62 个代谢物同义名

NERVONIC ACID (CONSTITUENT OF BORAGE SEED OIL); Nervonic acid, analytical reference material; nervonic acid, potassium salt(Z)-isomer; nervonic acid, sodium salt, (Z)-isomer; Nervonic acid, >=99\\% (capillary GC); 3F0366A4-A342-402E-B731-D54879FC86E7; Nervonic acid, analytical standard; cis-Delta(15)-tetracosenoic acid; 15-Tetracosenoic acid, (15Z)-; trans-tetracos-15-enoic acid; cis-Delta(15)-tetracosenoate; (15e)-Tetracos-15-Enoic Acid; (15Z)-tetracos-15-enoic acid; cis-Δ(15)-tetracosenoic acid; (15Z)-15-Tetracosenoic acid; 15-TETRACOSENOIC ACID, (Z)-; Tetracosenoic acid, 15-(Z)-; 15-TETRACOSENOIC ACID, CIS-; TETRACOSENOIC ACID, (15Z)-; (Z)-tetracos-15-enoic acid; (Z)-15-Tetracosenoic acid; (Z)-tetracos-15-enoicacid; cis-15-tetracosenoic acid; cis-15-Tetracosenic acid; (15Z)-Tetracosenoic acid; cis-15-Teracosenoic acid; cis-Δ(15)-tetracosenoate; (15Z)-tetracos-15-enoate; 15cis-tetracosenoic acid; z-15-Tetracosenoic acid; 15Z-tetracosenoic acid; (Z)-Tetracos-15-enoate; NERVONIC ACID [WHO-DD]; cis-15-Tetracosenoate; (Z)-15-tetracosenoate; 15-Tetracosenoic acid; 15cis-Tetracosenoate; cis-15-Tetracosenate; cis-selacholeic acid; (15Z)-Tetracosenoate; cis-15-Teracosenoate; NERVONIC ACID [DSC]; Fatty Acid 24:1 n-9; 15Z-tetracosenoate; ISOCONAZOLENITRATE; 15-Tetracosenoate; selacholeic acid; cis-selacholeate; UNII-91OQS788BE; Nervonic acid; FA(24:1(15Z)); Nervonsaeure; selacholeate; Nevonic acid; 91OQS788BE; FA(24:1n9); Nervonate; 24:1(N-9); C24:1n-9; FA(24:1); FA 24:1; tetracos-15-enoic acid



数据库引用编号

24 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

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

  • Xun Ang, Hong Chen, Jiqian Xiang, Fang Wei, Siew Young Quek. Lipase-Catalyzed Preparation and Optimization of Structured Phosphatidylcholine Containing Nervonic Acid. Molecules (Basel, Switzerland). 2024 Mar; 29(7):. doi: 10.3390/molecules29071539. [PMID: 38611818]
  • Magdalena Namiecinska, Paweł Piatek, Przemysław Lewkowicz. Nervonic Acid Synthesis Substrates as Essential Components in Profiled Lipid Supplementation for More Effective Central Nervous System Regeneration. International journal of molecular sciences. 2024 Mar; 25(7):. doi: 10.3390/ijms25073792. [PMID: 38612605]
  • Ximei Yang, Sen Lin, Ying Chen, Wen Chen, Dongming Lan, Yonghua Wang. Efficient Enzymatic Enrichment of High-purity Nervonic Acid from Malania oleifera Seed Oil. Journal of oleo science. 2024; 73(1):99-111. doi: 10.5650/jos.ess23170. [PMID: 38171735]
  • Ziyi Chen, Shu Liu, Hui Zhou, Meiyuan Wang, Shuhua Pei, Rongjin Wang, Zhongying Liu. UPLC-Q-TOF/MS based serum and urine metabolomics strategy to analyze the mechanism of nervonic acid in treating Alzheimer's disease. Journal of pharmaceutical and biomedical analysis. 2023 Dec; 240(?):115930. doi: 10.1016/j.jpba.2023.115930. [PMID: 38157740]
  • Hang Su, Penghui Shi, Zhaoshuang Shen, Huimin Meng, Ziyue Meng, Xingfeng Han, Yanna Chen, Weiming Fan, Yun Fa, Chunyu Yang, Fuli Li, Shi'an Wang. High-level production of nervonic acid in the oleaginous yeast Yarrowia lipolytica by systematic metabolic engineering. Communications biology. 2023 11; 6(1):1125. doi: 10.1038/s42003-023-05502-w. [PMID: 37935958]
  • Feixiang Liu, Zewei Lu, Tingting Lu, Manman Shi, Huimin Wang, Rong Wu, Jun Cao, Erzheng Su, Xiaoqiang Ma. Metabolic engineering of oleaginous yeast in the lipogenic phase enhances production of nervonic acid. Metabolic engineering. 2023 Nov; 80(?):193-206. doi: 10.1016/j.ymben.2023.10.001. [PMID: 37827446]
  • Tianquan Yang, Rengang Zhang, Xiaoling Tian, Gang Yao, Yuanting Shen, Sihai Wang, Jianfeng Mao, Guangyuan Li, Aizhong Liu, Weibang Sun, Yongpeng Ma. The chromosome-level genome assembly and genes involved in biosynthesis of nervonic acid of Malania oleifera. Scientific data. 2023 May; 10(1):298. doi: 10.1038/s41597-023-02218-8. [PMID: 37208438]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Kaifeng Wang, Lu Lin, Ping Wei, Rodrigo Ledesma-Amaro, Xiao-Jun Ji. Combining orthogonal plant and non-plant fatty acid biosynthesis pathways for efficient production of microbial oil enriched in nervonic acid in Yarrowia lipolytica. Bioresource technology. 2023 Apr; 378(?):129012. doi: 10.1016/j.biortech.2023.129012. [PMID: 37019413]
  • Yang Li, Fan Kong, Mingyang Zan, Liping Peng, Zhanzhong Wang, Qingyan Shu. Optimization technology and kinetic studies of Acer truncatum seed oil saponification and crystallization separation of nervonic acid. Journal of food science. 2022 Sep; 87(9):3925-3937. doi: 10.1111/1750-3841.16262. [PMID: 35904249]
  • Marcia R Terluk, Julianne Tieu, Siddhee A Sahasrabudhe, Ann Moser, Paul A Watkins, Gerald V Raymond, Reena V Kartha. Nervonic Acid Attenuates Accumulation of Very Long-Chain Fatty Acids and is a Potential Therapy for Adrenoleukodystrophy. Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics. 2022 04; 19(3):1007-1017. doi: 10.1007/s13311-022-01226-7. [PMID: 35378685]
  • Wangting Song, Ke Zhang, Teng Xue, Jiarui Han, Fangda Peng, Chunguang Ding, Feng Lin, Jiujun Li, Fat Tin Agassi Sze, Jianwen Gan, Xianyang Chen. Cognitive improvement effect of nervonic acid and essential fatty acids on rats ingesting Acer truncatum Bunge seed oil revealed by lipidomics approach. Food & function. 2022 Mar; 13(5):2475-2490. doi: 10.1039/d1fo03671h. [PMID: 35147628]
  • Abdulmoseen Segun Giwa, Nasir Ali. Perspectives of nervonic acid production by Yarrowia lipolytica. Biotechnology letters. 2022 Feb; 44(2):193-202. doi: 10.1007/s10529-022-03231-4. [PMID: 35119573]
  • Fatemeh-Rezaee Ashtiani, Hasan Jalili, Mahdi Rahaie, Mahsa Sedighi, Abdeltif Amrane. Effect of mixed culture of yeast and microalgae on acetyl-CoA carboxylase and Glycerol-3-phosphate acyltransferase expression. Journal of bioscience and bioengineering. 2021 Apr; 131(4):364-372. doi: 10.1016/j.jbiosc.2020.11.006. [PMID: 33341347]
  • Yuki Kageyama, Yasuhiko Deguchi, Kotaro Hattori, Sumiko Yoshida, Yu-Ichi Goto, Koki Inoue, Tadafumi Kato. Nervonic acid level in cerebrospinal fluid is a candidate biomarker for depressive and manic symptoms: A pilot study. Brain and behavior. 2021 04; 11(4):e02075. doi: 10.1002/brb3.2075. [PMID: 33599392]
  • Hiroki Umemoto, Saika Yasugi, Shinji Tsuda, Minoru Yoda, Takashi Ishiguro, Naoko Kaba, Tatsuki Itoh. Protective Effect of Nervonic Acid Against 6-Hydroxydopamine-Induced Oxidative Stress in PC-12 Cells. Journal of oleo science. 2021; 70(1):95-102. doi: 10.5650/jos.ess20262. [PMID: 33431776]
  • Laura J W Keppley, Susan J Walker, Alexis N Gademsey, Jason P Smith, Susanna R Keller, Mark Kester, Todd E Fox. Nervonic acid limits weight gain in a mouse model of diet-induced obesity. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2020 11; 34(11):15314-15326. doi: 10.1096/fj.202000525r. [PMID: 32959931]
  • Qiuyue Ma, Tianlin Sun, Shushun Li, Jing Wen, Lu Zhu, Tongming Yin, Kunyuan Yan, Xiao Xu, Shuxian Li, Jianfeng Mao, Ya-Nan Wang, Shuangxia Jin, Xing Zhao, Qianzhong Li. The Acer truncatum genome provides insights into nervonic acid biosynthesis. The Plant journal : for cell and molecular biology. 2020 11; 104(3):662-678. doi: 10.1111/tpj.14954. [PMID: 32772482]
  • Li Kong, Edgar Dawkins, Frederick Campbell, Edith Winkler, Rico J E Derks, Martin Giera, Frits Kamp, Harald Steiner, Alexander Kros. Photo-controlled delivery of very long chain fatty acids to cell membranes and modulation of membrane protein function. Biochimica et biophysica acta. Biomembranes. 2020 05; 1862(5):183200. doi: 10.1016/j.bbamem.2020.183200. [PMID: 31972163]
  • Małgorzata Szczuko, Małgorzata Kaczkan, Sylwia Małgorzewicz, Przemysław Rutkowski, Alicja Dębska-Ślizień, Ewa Stachowska. The C18:3n6/C22:4n6 ratio is a good lipid marker of chronic kidney disease (CKD) progression. Lipids in health and disease. 2020 Apr; 19(1):77. doi: 10.1186/s12944-020-01258-y. [PMID: 32303226]
  • Qi Li, Jia Chen, Xiuzhu Yu, Jin-Ming Gao. A mini review of nervonic acid: Source, production, and biological functions. Food chemistry. 2019 Dec; 301(?):125286. doi: 10.1016/j.foodchem.2019.125286. [PMID: 31382110]
  • Jiahui Yu, Tinglan Yuan, Xinghe Zhang, Qingzhe Jin, Wei Wei, Xingguo Wang. Quantification of Nervonic Acid in Human Milk in the First 30 Days of Lactation: Influence of Lactation Stages and Comparison with Infant Formulae. Nutrients. 2019 Aug; 11(8):. doi: 10.3390/nu11081892. [PMID: 31416149]
  • Karolina Konstantynowicz-Nowicka, Klaudia Berk, Adrian Chabowski, Irena Kasacka, Patrycja Bielawiec, Bartłomiej Łukaszuk, Ewa Harasim-Symbor. High-Fat Feeding in Time-Dependent Manner Affects Metabolic Routes Leading to Nervonic Acid Synthesis in NAFLD. International journal of molecular sciences. 2019 Aug; 20(15):. doi: 10.3390/ijms20153829. [PMID: 31387306]
  • Natalia Lewkowicz, Paweł Piątek, Magdalena Namiecińska, Małgorzata Domowicz, Radosław Bonikowski, Janusz Szemraj, Patrycja Przygodzka, Mariusz Stasiołek, Przemysław Lewkowicz. Naturally Occurring Nervonic Acid Ester Improves Myelin Synthesis by Human Oligodendrocytes. Cells. 2019 07; 8(8):. doi: 10.3390/cells8080786. [PMID: 31362382]
  • Małgorzata Szczuko, Małgorzata Kaczkan, Arleta Drozd, Dominika Maciejewska, Joanna Palma, Anna Owczarzak, Natalia Marczuk, Przemysław Rutkowski, Sylwia Małgorzewicz. Comparison of Fatty Acid Profiles in a Group of Female Patients with Chronic Kidney Diseases (CKD) and Metabolic Syndrome (MetS)⁻Similar Trends of Changes, Different Pathophysiology. International journal of molecular sciences. 2019 Apr; 20(7):. doi: 10.3390/ijms20071719. [PMID: 30959940]
  • Qiuyue Ma, Yanan Wang, Lu Zhu, Changwei Bi, Shuxian Li, Shushun Li, Jing Wen, Kunyuan Yan, Qianzhong Li. Characterization of the Complete Chloroplast Genome of Acer truncatum Bunge (Sapindales: Aceraceae): A New Woody Oil Tree Species Producing Nervonic Acid. BioMed research international. 2019; 2019(?):7417239. doi: 10.1155/2019/7417239. [PMID: 31886246]
  • Tianquan Yang, Qian Yu, Wei Xu, De-Zhu Li, Fu Chen, Aizhong Liu. Transcriptome analysis reveals crucial genes involved in the biosynthesis of nervonic acid in woody Malania oleifera oilseeds. BMC plant biology. 2018 Oct; 18(1):247. doi: 10.1186/s12870-018-1463-6. [PMID: 30340521]
  • Rongkai Wang, Pei Liu, Jinshuan Fan, Lingli Li. Comparative transcriptome analysis two genotypes of Acer truncatum Bunge seeds reveals candidate genes that influences seed VLCFAs accumulation. Scientific reports. 2018 10; 8(1):15504. doi: 10.1038/s41598-018-33999-3. [PMID: 30341360]
  • 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]
  • Yuki Kageyama, Takaoki Kasahara, Takemichi Nakamura, Kotaro Hattori, Yasuhiko Deguchi, Munehide Tani, Kenji Kuroda, Sumiko Yoshida, Yu-Ichi Goto, Koki Inoue, Tadafumi Kato. Plasma Nervonic Acid Is a Potential Biomarker for Major Depressive Disorder: A Pilot Study. The international journal of neuropsychopharmacology. 2018 03; 21(3):207-215. doi: 10.1093/ijnp/pyx089. [PMID: 29040586]
  • Miri Lee, Kyung-Mi Joo, Seunghye Choi, Su-Hyon Lee, Seol Yeong Kim, Young-Jin Chun, Dalwoong Choi, Kyung-Min Lim. Nervonoylceramide (C24:1Cer), a lipid biomarker for ocular irritants released from the 3D reconstructed human cornea-like epithelium, MCTT HCE™. Toxicology in vitro : an international journal published in association with BIBRA. 2018 Mar; 47(?):94-102. doi: 10.1016/j.tiv.2017.11.008. [PMID: 29155129]
  • Sandy Fillet, Carmen Ronchel, Carla Callejo, María-José Fajardo, Helena Moralejo, José L Adrio. Engineering Rhodosporidium toruloides for the production of very long-chain monounsaturated fatty acid-rich oils. Applied microbiology and biotechnology. 2017 Oct; 101(19):7271-7280. doi: 10.1007/s00253-017-8461-8. [PMID: 28812146]
  • C Austin Pickens, Lorraine M Sordillo, Sarah S Comstock, William S Harris, Kari Hortos, Bruce Kovan, Jenifer I Fenton. Plasma phospholipids, non-esterified plasma polyunsaturated fatty acids and oxylipids are associated with BMI. Prostaglandins, leukotrienes, and essential fatty acids. 2015 Apr; 95(?):31-40. doi: 10.1016/j.plefa.2014.12.001. [PMID: 25559239]
  • Dongxin Huai, Yuanyuan Zhang, Chunyu Zhang, Edgar B Cahoon, Yongming Zhou. Combinatorial Effects of Fatty Acid Elongase Enzymes on Nervonic Acid Production in Camelina sativa. PloS one. 2015; 10(6):e0131755. doi: 10.1371/journal.pone.0131755. [PMID: 26121034]
  • Suchitra Roy, Madhavi Dhobale, Kamini Dangat, Savita Mehendale, Girija Wagh, Sanjay Lalwani, Sadhana Joshi. Differential levels of long chain polyunsaturated fatty acids in women with preeclampsia delivering male and female babies. Prostaglandins, leukotrienes, and essential fatty acids. 2014 Nov; 91(5):227-32. doi: 10.1016/j.plefa.2014.07.002. [PMID: 25172358]
  • 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]
  • Gregory C Shearer, Juan J Carrero, Olof Heimbürger, Peter Barany, Peter Stenvinkel. Plasma fatty acids in chronic kidney disease: nervonic acid predicts mortality. Journal of renal nutrition : the official journal of the Council on Renal Nutrition of the National Kidney Foundation. 2012 Mar; 22(2):277-283. doi: 10.1053/j.jrn.2011.05.005. [PMID: 21775161]
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  • Karl-Göran Sabel, Cristina Lundqvist-Persson, Elsa Bona, Max Petzold, Birgitta Strandvik. Fatty acid patterns early after premature birth, simultaneously analysed in mothers' food, breast milk and serum phospholipids of mothers and infants. Lipids in health and disease. 2009 Jun; 8(?):20. doi: 10.1186/1476-511x-8-20. [PMID: 19515230]
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