22:4n6 (BioDeep_00001871871)
Main id: BioDeep_00000002672
代谢物信息卡片
(7Z,10Z,13Z,16Z)-Docosa-7,10,13,16-tetraenoic acid
化学式: C22H36O2 (332.2715156)
中文名称: 廿二碳四烯酸
谱图信息:
最多检出来源 () 0%
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)/b7-6-,10-9-,13-12-,16-15-
描述信息
The all-cis-isomer of a C22 polyunsaturated fatty acid having four double bonds in the 7-, 10-, 13- and 16-positions. One of the most abundant fatty acids in the early human brain.
同义名列表
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:53487
- KEGG: C16527
- PubChem: 5497181
- ChEMBL: CHEMBL1491103
- LipidMAPS: LMFA01030178
- CAS: 28874-58-0
- MetaboLights: MTBLC53487
- PubChem: 51090856
- NIKKAJI: J13.758H
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 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(0)
PharmGKB(0)
2 个相关的物种来源信息
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
- 9606 - Homo sapiens:
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] - Izabela Kania-Korwel, Xianai Wu, Kai Wang, Hans-Joachim Lehmler. Identification of lipidomic markers of chronic 3,3',4,4',5-pentachlorobiphenyl (PCB 126) exposure in the male rat liver.
Toxicology.
2017 09; 390(?):124-134. doi:
10.1016/j.tox.2017.09.005. [PMID: 28890136] - 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] - 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] - 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] - Mike VanRollins, Randall L Woltjer, Huiyong Yin, Jason D Morrow, Thomas J Montine. F2-dihomo-isoprostanes arise from free radical attack on adrenic acid.
Journal of lipid research.
2008 May; 49(5):995-1005. doi:
10.1194/jlr.m700503-jlr200. [PMID: 18250368] - R H M de Groot, G Hornstra, J Jolles. Exploratory study into the relation between plasma phospholipid fatty acid status and cognitive performance.
Prostaglandins, leukotrienes, and essential fatty acids.
2007 Mar; 76(3):165-72. doi:
10.1016/j.plefa.2007.01.001. [PMID: 17317131] - Elizabeth A Thomas, Jeffrey K Yao. Clozapine specifically alters the arachidonic acid pathway in mice lacking apolipoprotein D.
Schizophrenia research.
2007 Jan; 89(1-3):147-53. doi:
10.1016/j.schres.2006.08.011. [PMID: 17011169] - Fiona Moloney, Toh-Peng Yeow, Anne Mullen, John J Nolan, Helen M Roche. Conjugated linoleic acid supplementation, insulin sensitivity, and lipoprotein metabolism in patients with type 2 diabetes mellitus.
The American journal of clinical nutrition.
2004 Oct; 80(4):887-95. doi:
10.1093/ajcn/80.4.887. [PMID: 15447895] - Vasuki Wijendran, Peter Lawrence, Guan-Yeu Diau, G Boehm, P W Nathanielsz, J T Brenna. Significant utilization of dietary arachidonic acid is for brain adrenic acid in baboon neonates.
Journal of lipid research.
2002 May; 43(5):762-7. doi:
. [PMID: 11971947] - M Martínez, I Mougan. Fatty acid composition of human brain phospholipids during normal development.
Journal of neurochemistry.
1998 Dec; 71(6):2528-33. doi:
10.1046/j.1471-4159.1998.71062528.x. [PMID: 9832152] - M C Soares, M L Aléssio, C L Léger, M T Bluet-Pajot, H Clauser, A Enjalbert, C Kordon, D E Wandscheer. Effect of essential fatty acid deficiency on membrane fatty acid content and growth hormone stimulation of rat pituitaries during postnatal development.
Journal of lipid research.
1995 Jun; 36(6):1401-6. doi:
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Prostaglandins.
1992 Dec; 44(6):519-30. doi:
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Biochemical and biophysical research communications.
1992 Mar; 183(3):1047-55. doi:
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Lipids.
1990 Aug; 25(8):465-72. doi:
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1988 Mar; 959(2):134-42. doi:
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1988 Feb; 958(3):460-8. doi:
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1986 Jun; 27(6):629-36. doi:
10.1016/s0022-2275(20)38809-x. [PMID: 3746131] - W B Campbell, J R Falck, J R Okita, A R Johnson, K S Callahan. Synthesis of dihomoprostaglandins from adrenic acid (7,10,13,16-docosatetraenoic acid) by human endothelial cells.
Biochimica et biophysica acta.
1985 Oct; 837(1):67-76. doi:
10.1016/0005-2760(85)90086-4. [PMID: 3931686] - H Sprecher, M VanRollins, F Sun, A Wyche, P Needleman. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney.
The Journal of biological chemistry.
1982 Apr; 257(7):3912-8. doi:
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1981 Jul; 22(5):763-9. doi:
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