Adrenic acid (BioDeep_00000002672)

 

Secondary id: BioDeep_00001871871

human metabolite Endogenous blood metabolite


代谢物信息卡片


7,10,13,16-Docosatetraenoic acid (van) adrenic acid

化学式: C22H36O2 (332.2715156)
中文名称: 廿二碳四烯酸, 7Z,10Z,13Z,16Z-二十二碳四烯酸, 顺-7,10,13,16-二十二碳四烯酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.25%

分子结构信息

SMILES: C(CC(=O)O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
InChI: InChI=1S/C22H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,23,24)

描述信息

Adrenic acid, also known as 7,10,13,16-docosatetraenoic acid or adrenate, 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. Adrenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Adrenic acid can be found in blood and in human myelin tissue. Within the cell, adrenic acid is primarily located in the cytoplasm, in the membrane (predicted from logP), and in the peroxisome. It can also be found in the extracellular space. In humans, adrenic acid is involved in alpha-linolenic acid and linoleic acid metabolism. Docosatetraenoic acid designates any straight chain 22:4 fatty acid. In particular, all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the trivial name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells into biologically active products, such as dihomoprostaglandins and dihomo-epoxyeicosatrienoic acids (dihomo-EETs) (Wikipedia). Adrenic acid, which is a prostacyclin inhibitor, appears to be a potential prothrombotic agent (PMID: 1642692).
Adrenic acid, which is a prostacyclin inhibitor, appears to be potential prothrombotic agent. (PMID 1642692) [HMDB]

同义名列表

22 个代谢物同义名

7,10,13,16-Docosatetraenoic acid (van) adrenic acid; (7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid; cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeure; 7,10,13,16-Docosatetraenoic acid (van) adrenate; (7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoate; all-cis-7,10,13,16-Docosatetraenoic acid; all-cis-7,10,13,16-Docosatetraenoate; 7Z,10Z,13Z,16Z-docosatetraenoic acid; (7Z,10Z,13Z,16Z)-Docosatetraenoate; Docosa-7,10,13,16-tetraenoic acid; 7Z,10Z,13Z,16Z-Docosatetraenoate; 7,10,13,16-docosatetraenoic acid; 7,10,13,16-Docosatetraenoate; FA(22:4(7Z,10Z,13Z,16Z)); Adrenic acid, (Z)-isomer; docosatetraenoic acid; C22:4n-6,9,12,15; adrenic acid; Adrenate; FA 22:4; 22:4n6; 7Z,10Z,13Z,16Z-Docosatetraenoic acid



数据库引用编号

19 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

7 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(6)

PharmGKB(0)

4 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

  • Chia-Hsiu Wu, Wen-Li Hsu, Ching-Chung Tsai, How-Ran Chao, Ching-Ying Wu, Yi-Hsuan Chen, Yun-Ru Lai, Chu-Huang Chen, Ming-Hsien Tsai. 7,10,13,16-Docosatetraenoic acid impairs neurobehavioral development by increasing reactive oxidative species production in Caenorhabditis elegans. Life sciences. 2023 Apr; 319(?):121500. doi: 10.1016/j.lfs.2023.121500. [PMID: 36796717]
  • Yan Wang, Xingyue Chen, Wenli Fan, Xujia Zhang, Siyuan Zhan, Tao Zhong, Jiazhong Guo, Jiaxue Cao, Li Li, Hongping Zhang, Linjie Wang. Integrated application of metabolomics and RNA-seq reveals thermogenic regulation in goat brown adipose tissues. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2021 09; 35(9):e21868. doi: 10.1096/fj.202100493rr. [PMID: 34449920]
  • Ji-Yoon Lee, Miso Nam, Hye Young Son, Kwangbeom Hyun, Seo Young Jang, Jong Woo Kim, Min Wook Kim, Youngae Jung, Eunji Jang, Seon-Jin Yoon, Jungeun Kim, Jihye Kim, Jinho Seo, Jeong-Ki Min, Kyoung-Jin Oh, Baek-Soo Han, Won Kon Kim, Kwang-Hee Bae, Jaewhan Song, Jaehoon Kim, Yong-Min Huh, Geum-Sook Hwang, Eun-Woo Lee, Sang Chul Lee. Polyunsaturated fatty acid biosynthesis pathway determines ferroptosis sensitivity in gastric cancer. Proceedings of the National Academy of Sciences of the United States of America. 2020 12; 117(51):32433-32442. doi: 10.1073/pnas.2006828117. [PMID: 33288688]
  • Cadiele Oliana Reichert, Fábio Alessandro de Freitas, Juliana Sampaio-Silva, Leonardo Rokita-Rosa, Priscila de Lima Barros, Debora Levy, Sérgio Paulo Bydlowski. Ferroptosis Mechanisms Involved in Neurodegenerative Diseases. International journal of molecular sciences. 2020 Nov; 21(22):. doi: 10.3390/ijms21228765. [PMID: 33233496]
  • Mary Xylaki, Ioanna Boumpoureka, Maroula G Kokotou, Theodoros Marras, Georgia Papadimitriou, Ismini Kloukina, Victoria Magrioti, George Kokotos, Kostas Vekrellis, Evangelia Emmanouilidou. Changes in the cellular fatty acid profile drive the proteasomal degradation of α-synuclein and enhance neuronal survival. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2020 11; 34(11):15123-15145. doi: 10.1096/fj.202001344r. [PMID: 32931072]
  • Souha Hammouda, Imen Ghzaiel, Wided Khamlaoui, Sonia Hammami, Samia Younes Mhenni, Slim Samet, Mohamed Hammami, Amira Zarrouk. Genetic variants in FADS1 and ELOVL2 increase level of arachidonic acid and the risk of Alzheimer's disease in the Tunisian population. Prostaglandins, leukotrienes, and essential fatty acids. 2020 09; 160(?):102159. doi: 10.1016/j.plefa.2020.102159. [PMID: 32682282]
  • Ángel Sánchez-Illana, Vidhi Shah, José David Piñeiro-Ramos, Juliann M Di Fiore, Guillermo Quintás, Thomas M Raffay, Peter M MacFarlane, Richard J Martin, Julia Kuligowski. Adrenic acid non-enzymatic peroxidation products in biofluids of moderate preterm infants. Free radical biology & medicine. 2019 10; 142(?):107-112. doi: 10.1016/j.freeradbiomed.2019.02.024. [PMID: 30818053]
  • Anna Marco-Ramell, Sara Tulipani, Magali Palau-Rodriguez, Raul Gonzalez-Dominguez, Antonio Miñarro, Olga Jauregui, Alex Sanchez-Pla, Manuel Macias-Gonzalez, Fernando Cardona, Francisco J Tinahones, Cristina Andres-Lacueva. Untargeted Profiling of Concordant/Discordant Phenotypes of High Insulin Resistance and Obesity To Predict the Risk of Developing Diabetes. Journal of proteome research. 2018 07; 17(7):2307-2317. doi: 10.1021/acs.jproteome.7b00855. [PMID: 29905079]
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  • Saut Horas H Nababan, Shin Nishiumi, Yuki Kawano, Takashi Kobayashi, Masaru Yoshida, Takeshi Azuma. Adrenic acid as an inflammation enhancer in non-alcoholic fatty liver disease. Archives of biochemistry and biophysics. 2017 06; 623-624(?):64-75. doi: 10.1016/j.abb.2017.04.009. [PMID: 28456640]
  • Kin Sum Leung, Hok Fung Chan, Ho Hang Leung, Jean-Marie Galano, Camille Oger, Thierry Durand, Jetty Chung-Yung Lee. Short-time UVA exposure to human keratinocytes instigated polyunsaturated fatty acid without inducing lipid peroxidation. Free radical research. 2017 Mar; 51(3):269-280. doi: 10.1080/10715762.2017.1300885. [PMID: 28301979]
  • Valerian E Kagan, Gaowei Mao, Feng Qu, Jose Pedro Friedmann Angeli, Sebastian Doll, Claudette St Croix, Haider Hussain Dar, Bing Liu, Vladimir A Tyurin, Vladimir B Ritov, Alexandr A Kapralov, Andrew A Amoscato, Jianfei Jiang, Tamil Anthonymuthu, Dariush Mohammadyani, Qin Yang, Bettina Proneth, Judith Klein-Seetharaman, Simon Watkins, Ivet Bahar, Joel Greenberger, Rama K Mallampalli, Brent R Stockwell, Yulia Y Tyurina, Marcus Conrad, Hülya Bayır. Oxidized arachidonic and adrenic PEs navigate cells to ferroptosis. Nature chemical biology. 2017 Jan; 13(1):81-90. doi: 10.1038/nchembio.2238. [PMID: 27842066]
  • Kunio Yui, George Imataka, Yohei Kawasak, Hiroshi Yamada. Increased ω-3 polyunsaturated fatty acid/arachidonic acid ratios and upregulation of signaling mediator in individuals with autism spectrum disorders. Life sciences. 2016 Jan; 145(?):205-12. doi: 10.1016/j.lfs.2015.12.039. [PMID: 26724495]
  • Ming Long Sirius Chung, Jean-Marie Galano, Camille Oger, Thierry Durand, Jetty Chung-Yung Lee. Hyperoxia elevates adrenic acid peroxidation in marine fish and is associated with reproductive pheromone mediators. Marine drugs. 2015 Apr; 13(4):2215-32. doi: 10.3390/md13042215. [PMID: 25874920]
  • Jean-Marie Galano, Jetty Chung-Yung Lee, Cecile Gladine, Blandine Comte, Jean-Yves Le Guennec, Camille Oger, Thierry Durand. Non-enzymatic cyclic oxygenated metabolites of adrenic, docosahexaenoic, eicosapentaenoic and α-linolenic acids; bioactivities and potential use as biomarkers. Biochimica et biophysica acta. 2015 Apr; 1851(4):446-55. doi: 10.1016/j.bbalip.2014.11.004. [PMID: 25463478]
  • Aurélien de La Torre, Yiu Yiu Lee, Camille Oger, Per Torp Sangild, Thierry Durand, Jetty Chung-Yung Lee, Jean-Marie Galano. Synthesis, discovery, and quantitation of dihomo-isofurans: biomarkers for in vivo adrenic acid peroxidation. Angewandte Chemie (International ed. in English). 2014 Jun; 53(24):6249-52. doi: 10.1002/anie.201402440. [PMID: 24839059]
  • Juliana S Vaz, Gilberto Kac, Antonio E Nardi, Joseph R Hibbeln. Omega-6 fatty acids and greater likelihood of suicide risk and major depression in early pregnancy. Journal of affective disorders. 2014 Jan; 152-154(?):76-82. doi: 10.1016/j.jad.2013.04.045. [PMID: 23726775]
  • Thierry Durand, Claudio De Felice, Cinzia Signorini, Camille Oger, Valérie Bultel-Poncé, Alexandre Guy, Jean-Marie Galano, Silvia Leoncini, Lucia Ciccoli, Alessandra Pecorelli, Giuseppe Valacchi, Joussef Hayek. F(2)-Dihomo-isoprostanes and brain white matter damage in stage 1 Rett syndrome. Biochimie. 2013 Jan; 95(1):86-90. doi: 10.1016/j.biochi.2012.09.017. [PMID: 23009927]
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  • Saki Kakutani, Yoshiyuki Ishikura, Norifumi Tateishi, Chika Horikawa, Hisanori Tokuda, Masanori Kontani, Hiroshi Kawashima, Yutaka Sakakibara, Yoshinobu Kiso, Hiroshi Shibata, Ikuo Morita. Supplementation of arachidonic acid-enriched oil increases arachidonic acid contents in plasma phospholipids, but does not increase their metabolites and clinical parameters in Japanese healthy elderly individuals: a randomized controlled study. Lipids in health and disease. 2011 Dec; 10(?):241. doi: 10.1186/1476-511x-10-241. [PMID: 22188761]
  • Cornelia Enzenbach, Janine Kröger, Vera Zietemann, Eugène H J M Jansen, Andreas Fritsche, Frank Döring, Heiner Boeing, Matthias B Schulze. Erythrocyte membrane phospholipid polyunsaturated fatty acids are related to plasma C-reactive protein and adiponectin in middle-aged German women and men. European journal of nutrition. 2011 Dec; 50(8):625-36. doi: 10.1007/s00394-011-0169-4. [PMID: 21301856]
  • Claudio De Felice, Cinzia Signorini, Thierry Durand, Camille Oger, Alexandre Guy, Valérie Bultel-Poncé, Jean-Marie Galano, Lucia Ciccoli, Silvia Leoncini, Maurizio D'Esposito, Stefania Filosa, Alessandra Pecorelli, Giuseppe Valacchi, Joussef Hayek. F2-dihomo-isoprostanes as potential early biomarkers of lipid oxidative damage in Rett syndrome. Journal of lipid research. 2011 Dec; 52(12):2287-2297. doi: 10.1194/jlr.p017798. [PMID: 21917727]
  • Junya Matsumoto, Yuki Sugiura, Dai Yuki, Takahiro Hayasaka, Naoko Goto-Inoue, Nobuhiro Zaima, Yasuto Kunii, Akira Wada, Qiaohui Yang, Keisuke Nishiura, Hiroyasu Akatsu, Akira Hori, Yoshio Hashizume, Takayuki Yamamoto, Keiko Ikemoto, Mitsutoshi Setou, Shin-ichi Niwa. Abnormal phospholipids distribution in the prefrontal cortex from a patient with schizophrenia revealed by matrix-assisted laser desorption/ionization imaging mass spectrometry. Analytical and bioanalytical chemistry. 2011 Jun; 400(7):1933-43. doi: 10.1007/s00216-011-4909-3. [PMID: 21461619]
  • Afaf K El-Ansary, Abir G Ben Bacha, Layla Y Al-Ayahdi. Impaired plasma phospholipids and relative amounts of essential polyunsaturated fatty acids in autistic patients from Saudi Arabia. Lipids in health and disease. 2011 Apr; 10(?):63. doi: 10.1186/1476-511x-10-63. [PMID: 21513514]
  • Irina Guschina, Steve Millership, Valerie O'Donnell, Natalia Ninkina, John Harwood, Vladimir Buchman. Lipid classes and fatty acid patterns are altered in the brain of γ-synuclein null mutant mice. Lipids. 2011 Feb; 46(2):121-30. doi: 10.1007/s11745-010-3486-0. [PMID: 20963507]
  • Miki Igarashi, Kaizong Ma, Fei Gao, Hyung-Wook Kim, Stanley I Rapoport, Jagadeesh S Rao. Disturbed choline plasmalogen and phospholipid fatty acid concentrations in Alzheimer's disease prefrontal cortex. Journal of Alzheimer's disease : JAD. 2011; 24(3):507-17. doi: 10.3233/jad-2011-101608. [PMID: 21297269]
  • Vuokko Aarnio, Marko Lehtonen, Markus Storvik, James C Callaway, Merja Lakso, Garry Wong. Caenorhabditis Elegans Mutants Predict Regulation of Fatty Acids and Endocannabinoids by the CYP-35A Gene Family. Frontiers in pharmacology. 2011; 2(?):12. doi: 10.3389/fphar.2011.00012. [PMID: 21687507]
  • James R Petrie, Surinder P Singh. Expanding the docosahexaenoic acid food web for sustainable production: engineering lower plant pathways into higher plants. AoB PLANTS. 2011; 2011(?):plr011. doi: 10.1093/aobpla/plr011. [PMID: 22476481]
  • Stephanie Van Biervliet, Jean-Pierre Van Biervliet, Eddy Robberecht, Armand Christophe. Fatty acid composition of serum phospholipids in cystic fibrosis (CF) patients with or without CF related liver disease. Clinical chemistry and laboratory medicine. 2010 Dec; 48(12):1751-5. doi: 10.1515/cclm.2010.336. [PMID: 20961201]
  • Aihua Liu, James Chang, Yanhua Lin, Zhengqing Shen, Paul S Bernstein. Long-chain and very long-chain polyunsaturated fatty acids in ocular aging and age-related macular degeneration. Journal of lipid research. 2010 Nov; 51(11):3217-29. doi: 10.1194/jlr.m007518. [PMID: 20688753]
  • Li Rong Shen, Chao Qiang Lai, Xiang Feng, Laurence D Parnell, Jian Bo Wan, Jing D Wang, Duo Li, Jose M Ordovas, Jing X Kang. Drosophila lacks C20 and C22 PUFAs. Journal of lipid research. 2010 Oct; 51(10):2985-92. doi: 10.1194/jlr.m008524. [PMID: 20656917]
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  • Songsri Kaewsuwan, Nantavan Bunyapraphatsara, David J Cove, Ralph S Quatrano, Pichit Chodok. High level production of adrenic acid in Physcomitrella patens using the algae Pavlova sp. Delta(5)-elongase gene. Bioresource technology. 2010 Jun; 101(11):4081-8. doi: 10.1016/j.biortech.2009.12.138. [PMID: 20106658]
  • Robert Kleemann, Marjan van Erk, Lars Verschuren, Anita M van den Hoek, Maud Koek, Peter Y Wielinga, Annie Jie, Linette Pellis, Ivana Bobeldijk-Pastorova, Thomas Kelder, Karin Toet, Suzan Wopereis, Nicole Cnubben, Chris Evelo, Ben van Ommen, Teake Kooistra. Time-resolved and tissue-specific systems analysis of the pathogenesis of insulin resistance. PloS one. 2010 Jan; 5(1):e8817. doi: 10.1371/journal.pone.0008817. [PMID: 20098690]
  • Aldona Pietrzak, Anna Michalak-Stoma, Grazyna Chodorowska, Jacek C Szepietowski. Lipid disturbances in psoriasis: an update. Mediators of inflammation. 2010; 2010(?):. doi: 10.1155/2010/535612. [PMID: 20706605]
  • Stefanie Ebert, Karin Weigelt, Yana Walczak, Wolfgang Drobnik, Richard Mauerer, David A Hume, Bernhard H F Weber, Thomas Langmann. Docosahexaenoic acid attenuates microglial activation and delays early retinal degeneration. Journal of neurochemistry. 2009 Sep; 110(6):1863-75. doi: 10.1111/j.1471-4159.2009.06286.x. [PMID: 19627444]
  • Nahed Hussein, Irina Fedorova, Toru Moriguchi, Kei Hamazaki, Hee-Yong Kim, Junji Hoshiba, Norman Salem. Artificial rearing of infant mice leads to n-3 fatty acid deficiency in cardiac, neural and peripheral tissues. Lipids. 2009 Aug; 44(8):685-702. doi: 10.1007/s11745-009-3318-2. [PMID: 19588181]
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