18-Hydroxylinoleic acid (BioDeep_00001872860)
代谢物信息卡片
18-Hydroxylinoleic acid
化学式: C18H32O3 (296.2351322)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C(CCCC=CCC=CCCCCCO)CCCC(=O)O
InChI: InChI=1S/C18H32O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-2,5,7,19H,3-4,6,8-17H2,(H,20,21)/b2-1-,7-5-
描述信息
An omega-hydroxy fatty acid that is linoleic acid in which one of the terminal methyl hydrogens has been replaced by a hydroxy group.
同义名列表
1 个代谢物同义名
相关代谢途径
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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)
0 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
- Johanna von Gerichten, Annette L West, Nicola A Irvine, Elizabeth A Miles, Philip C Calder, Karen A Lillycrop, Barbara A Fielding, Graham C Burdge. The Partitioning of Newly Assimilated Linoleic and α-Linolenic Acids Between Synthesis of Longer-Chain Polyunsaturated Fatty Acids and Hydroxyoctadecaenoic Acids Is a Putative Branch Point in T-Cell Essential Fatty Acid Metabolism.
Frontiers in immunology.
2021; 12(?):740749. doi:
10.3389/fimmu.2021.740749. [PMID: 34675928] - Agnieszka Stawarska, Małgorzata Jelińska, Julia Czaja, Ewelina Pacześniak, Barbara Bobrowska-Korczak. Oils' Impact on Comprehensive Fatty Acid Analysis and Their Metabolites in Rats.
Nutrients.
2020 Apr; 12(5):. doi:
10.3390/nu12051232. [PMID: 32349264] - Marcin Banaszczak, Dominika Maciejewska, Arleta Drozd, Karina Ryterska, Dominika Jamioł Milc, Joanna Raszeja-Wyszomirska, Ewa Wunsch, Pedro González-Muniesa, Ewa Stachowska. 5-Lipooxygenase Derivatives as Serum Biomarkers of a Successful Dietary Intervention in Patients with NonAlcoholic Fatty Liver Disease.
Medicina (Kaunas, Lithuania).
2020 Feb; 56(2):. doi:
10.3390/medicina56020058. [PMID: 32028646] - Katarzyna Grzesiak, Aleksandra Rył, Ewa Stachowska, Marcin Słojewski, Iwona Rotter, Weronika Ratajczak, Olimpia Sipak, Małgorzata Piasecka, Barbara Dołęgowska, Maria Laszczyńska. The Relationship between Eicosanoid Levels and Serum Levels of Metabolic and Hormonal Parameters Depending on the Presence of Metabolic Syndrome in Patients with Benign Prostatic Hyperplasia.
International journal of environmental research and public health.
2019 03; 16(6):. doi:
10.3390/ijerph16061006. [PMID: 30897712] - David Fuchs, Mats Hamberg, C Magnus Sköld, Åsa M Wheelock, Craig E Wheelock. An LC-MS/MS workflow to characterize 16 regio- and stereoisomeric trihydroxyoctadecenoic acids.
Journal of lipid research.
2018 10; 59(10):2025-2033. doi:
10.1194/jlr.d087429. [PMID: 30065010] - J R Jensen, M H Pitcher, Z X Yuan, C E Ramsden, A F Domenichiello. Concentrations of oxidized linoleic acid derived lipid mediators in the amygdala and periaqueductal grey are reduced in a mouse model of chronic inflammatory pain.
Prostaglandins, leukotrienes, and essential fatty acids.
2018 08; 135(?):128-136. doi:
10.1016/j.plefa.2018.07.015. [PMID: 30103924] - Aya Umeno, Mayuko Morita, Yasukazu Yoshida, Yuji Naito, Etsuo Niki. Isomer distribution of hydroxyoctadecadienoates (HODE) and hydroxyeicosatetraenoates (HETE) produced in the plasma oxidation mediated by peroxyl radical, peroxynitrite, hypochlorite, 15-lipoxygenase, and singlet oxygen.
Archives of biochemistry and biophysics.
2017 12; 635(?):96-101. doi:
10.1016/j.abb.2017.10.023. [PMID: 29097313] - Hiroko Fukui, Shigehisa Endoh, Mototada Shichiri, Noriko Ishida, Yoshihisa Hagihara, Yasukazu Yoshida, Hitoshi Iwahashi, Masanori Horie. The induction of lipid peroxidation during the acute oxidative stress response induced by intratracheal instillation of fine crystalline silica particles in rats.
Toxicology and industrial health.
2016 Aug; 32(8):1430-1437. doi:
10.1177/0748233714564415. [PMID: 25552537] - Kohji Azumagawa, Makoto Mino, Noriko Ishida, Mototada Shichiri, Yasushi Shigeri, Yasukazu Yoshida, Hiroshi Tamai. Dynamics of hydroxyoctadecadienoic acid in epilepsy patients treated with valproic acid.
Pediatrics international : official journal of the Japan Pediatric Society.
2016 Jan; 58(1):45-8. doi:
10.1111/ped.12756. [PMID: 26190297] - K Yoshino, A Umeno, M Shichiri, H Watanabe, N Ishida, M Kojima, S Iwaki, Y Hagihara, M Nakamura, Y Yoshida. Biomarkers for the evaluation of immunological properties during the shikoku walking pilgrimage.
Journal of biological regulators and homeostatic agents.
2015 Jan; 29(1):51-62. doi:
NULL. [PMID: 25864741] - Yasukazu Yoshida, Aya Umeno, Yoko Akazawa, Mototada Shichiri, Kazutoshi Murotomi, Masanori Horie. Chemistry of lipid peroxidation products and their use as biomarkers in early detection of diseases.
Journal of oleo science.
2015; 64(4):347-56. doi:
10.5650/jos.ess14281. [PMID: 25766928] - Jinbo Liu, Peter J Mazzone, Juan P Cata, Andrea Kurz, Maria Bauer, Edward J Mascha, Daniel I Sessler. Serum free fatty acid biomarkers of lung cancer.
Chest.
2014 Sep; 146(3):670-679. doi:
10.1378/chest.13-2568. [PMID: 24743744] - Xiaofei Qin, Chunguang Qiu, Luosha Zhao. Lysophosphatidylcholine perpetuates macrophage polarization toward classically activated phenotype in inflammation.
Cellular immunology.
2014 May; 289(1-2):185-90. doi:
10.1016/j.cellimm.2014.04.010. [PMID: 24841857] - Yoshiro Saito, Noriko Noguchi. 7-Hydroxycholestrol as a possible biomarker of cellular lipid peroxidation: difference between cellular and plasma lipid peroxidation.
Biochemical and biophysical research communications.
2014 Apr; 446(3):741-4. doi:
10.1016/j.bbrc.2013.12.083. [PMID: 24380859] - Tamio Yamaguchi, Clara Lysecki, Ashleigh Reid, Shizuko Nagao, Harold M Aukema. Renal cyclooxygenase products are higher and lipoxygenase products are lower in early disease in the pcy mouse model of adolescent nephronophthisis.
Lipids.
2014 Jan; 49(1):39-47. doi:
10.1007/s11745-013-3859-2. [PMID: 24178445] - Adolfo García-Sastre. Lessons from lipids in the fight against influenza.
Cell.
2013 Jul; 154(1):22-3. doi:
10.1016/j.cell.2013.06.024. [PMID: 23827671] - Vincent C Tam, Oswald Quehenberger, Christine M Oshansky, Rosa Suen, Aaron M Armando, Piper M Treuting, Paul G Thomas, Edward A Dennis, Alan Aderem. Lipidomic profiling of influenza infection identifies mediators that induce and resolve inflammation.
Cell.
2013 Jul; 154(1):213-27. doi:
10.1016/j.cell.2013.05.052. [PMID: 23827684] - Aya Umeno, Mototada Shichiri, Noriko Ishida, Yoshiko Hashimoto, Kaori Abe, Masatoshi Kataoka, Kohzoh Yoshino, Yoshihisa Hagihara, Nanako Aki, Makoto Funaki, Yasuhiko Asada, Yasukazu Yoshida. Singlet oxygen induced products of linoleates, 10- and 12-(Z,E)-hydroxyoctadecadienoic acids (HODE), can be potential biomarkers for early detection of type 2 diabetes.
PloS one.
2013; 8(5):e63542. doi:
10.1371/journal.pone.0063542. [PMID: 23691063] - Joanna Raszeja-Wyszomirska, Krzysztof Safranow, Małgorzata Milkiewicz, Piotr Milkiewicz, Agnieszka Szynkowska, Ewa Stachowska. Lipidic last breath of life in patients with alcoholic liver disease.
Prostaglandins & other lipid mediators.
2012 Oct; 99(1-2):51-6. doi:
10.1016/j.prostaglandins.2012.06.001. [PMID: 22706383] - Tyler Stevens, Michael P Berk, Rocio Lopez, Yoon-Mi Chung, Renliang Zhang, Mansour A Parsi, Mary P Bronner, Ariel E Feldstein. Lipidomic profiling of serum and pancreatic fluid in chronic pancreatitis.
Pancreas.
2012 May; 41(4):518-22. doi:
10.1097/mpa.0b013e31823ca306. [PMID: 22504378] - Yutaka Hirashima, Masaru Doshi, Nakamasa Hayashi, Shunro Endo, Yoko Akazawa, Mototada Shichiri, Yasukazu Yoshida. Plasma platelet-activating factor-acetyl hydrolase activity and the levels of free forms of biomarker of lipid peroxidation in cerebrospinal fluid of patients with aneurysmal subarachnoid hemorrhage.
Neurosurgery.
2012 Mar; 70(3):602-9. doi:
10.1227/neu.0b013e3182333c69. [PMID: 21866060] - Fredrik Jernerén, Felipe Eng, Mats Hamberg, Ernst H Oliw. Linolenate 9R-dioxygenase and allene oxide synthase activities of Lasiodiplodia theobromae.
Lipids.
2012 Jan; 47(1):65-73. doi:
10.1007/s11745-011-3622-5. [PMID: 22048860] - Mototada Shichiri, Yasukazu Yoshida, Noriko Ishida, Yoshihisa Hagihara, Hitoshi Iwahashi, Hiroshi Tamai, Etsuo Niki. α-Tocopherol suppresses lipid peroxidation and behavioral and cognitive impairments in the Ts65Dn mouse model of Down syndrome.
Free radical biology & medicine.
2011 Jun; 50(12):1801-11. doi:
10.1016/j.freeradbiomed.2011.03.023. [PMID: 21447382] - Chenghui Xie, Jie Kang, Ramona Burris, Matthew E Ferguson, Alexander G Schauss, Shanmugam Nagarajan, Xianli Wu. Açaí juice attenuates atherosclerosis in ApoE deficient mice through antioxidant and anti-inflammatory activities.
Atherosclerosis.
2011 Jun; 216(2):327-33. doi:
10.1016/j.atherosclerosis.2011.02.035. [PMID: 21411096] - Lukas Kubala, Kara R Schmelzer, Anna Klinke, Hana Kolarova, Stephan Baldus, Bruce D Hammock, Jason P Eiserich. Modulation of arachidonic and linoleic acid metabolites in myeloperoxidase-deficient mice during acute inflammation.
Free radical biology & medicine.
2010 May; 48(10):1311-20. doi:
10.1016/j.freeradbiomed.2010.02.010. [PMID: 20156554] - Yasukazu Yoshida, Yasuharu Imai, Yoshiyuki Sawai, Yoshiro Saito, Jiaofei Cao, Kazuto Fukuda, Etsuo Niki. Hydroxyoctadecadienoic acid as a potential biomarker for oxidative stress in patients with chronic hepatitis C.
Journal of gastroenterology and hepatology.
2010 Jan; 25(1):107-15. doi:
10.1111/j.1440-1746.2009.05928.x. [PMID: 19780883] - Yasukazu Yoshida, Nanako Itoh, Mieko Hayakawa, Yoko Habuchi, Yoshiro Saito, Yoshitane Tsukamoto, Osamu Cynshi, Kou-ichi Jishage, Hiroyuki Arai, Etsuo Niki. The role of alpha-tocopherol in motor hypofunction with aging in alpha-tocopherol transfer protein knockout mice as assessed by oxidative stress biomarkers.
The Journal of nutritional biochemistry.
2010 Jan; 21(1):66-76. doi:
10.1016/j.jnutbio.2008.10.006. [PMID: 19157826] - Yasukazu Yoshida, Atsushi Yoshikawa, Tomoya Kinumi, Yoko Ogawa, Yoshiro Saito, Kazuyuki Ohara, Hirokazu Yamamoto, Yasuharu Imai, Etsuo Niki. Hydroxyoctadecadienoic acid and oxidatively modified peroxiredoxins in the blood of Alzheimer's disease patients and their potential as biomarkers.
Neurobiology of aging.
2009 Feb; 30(2):174-85. doi:
10.1016/j.neurobiolaging.2007.06.012. [PMID: 17688973] - Pelin Cengiz, Frank Zemlan, Richard Ellenbogen, Douglas Hawkins, Jerry J Zimmerman. Cerebrospinal fluid cleaved-tau protein and 9-hydroxyoctadecadienoic acid concentrations in pediatric patients with hydrocephalus.
Pediatric critical care medicine : a journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies.
2008 Sep; 9(5):524-9. doi:
10.1097/pcc.0b013e3181849dc9. [PMID: 18679140] - Yasukazu Yoshida, Shintaro Kodai, Shigekazu Takemura, Yukiko Minamiyama, Etsuo Niki. Simultaneous measurement of F2-isoprostane, hydroxyoctadecadienoic acid, hydroxyeicosatetraenoic acid, and hydroxycholesterols from physiological samples.
Analytical biochemistry.
2008 Aug; 379(1):105-15. doi:
10.1016/j.ab.2008.04.028. [PMID: 18482573] - Hideyuki Nushida, Junko Adachi, Atsuko Takeuchi, Migiwa Asano, Yasuhiro Ueno. Adipocere formation via hydrogenation of linoleic acid in a victim kept under dry concealment.
Forensic science international.
2008 Mar; 175(2-3):160-5. doi:
10.1016/j.forsciint.2007.06.008. [PMID: 17644293] - Yasukazu Yoshida, Etsuo Niki. Relative susceptibilities of linoleates and cholesterol to oxidation assessed by total hydroxyoctadecadienoic acid and 7-hydroxycholesterol.
Journal of oleo science.
2008; 57(7):407-14. doi:
10.5650/jos.57.407. [PMID: 18536511] - Yasukazu Yoshida, Mieko Hayakawa, Etsuo Niki. Evaluation of the antioxidant effects of coffee and its components using the biomarkers hydroxyoctadecadienoic acid and isoprostane.
Journal of oleo science.
2008; 57(12):691-7. doi:
10.5650/jos.57.691. [PMID: 19001782] - Yasukazu Yoshida, Mieko Hayakawa, Osamu Cynshi, Kou-ichi Jishage, Etsuo Niki. Acceleration of lipid peroxidation in alpha-tocopherol transfer protein-knockout mice following the consumption of drinking water containing a radical initiator.
Journal of oleo science.
2008; 57(10):577-83. doi:
10.5650/jos.57.577. [PMID: 18781058] - Yasukazu Yoshida, Mieko Hayakawa, Nanako Itoh, Yoko Habuchi, Ruriko Inoue, Zhi-Hua Chen, Jiaofei Cao, Osamu Cynshi, Kou-Ichi Jishage, Etsuo Niki. Antioxidant effects of 2,3-dihydro-5-hydroxy-4,6-di-tert-butyl-2,2-dipentylbenzofuran and alpha-tocopherol in hyperlipidemic mice as evaluated by hydroxyoctadecadienoic acid and 7-hydroxycholesterol.
Biochemical pharmacology.
2007 Oct; 74(7):1010-9. doi:
10.1016/j.bcp.2007.07.020. [PMID: 17706610] - Yasukazu Yoshida, Yoshiro Saito, Mieko Hayakawa, Yoko Habuchi, Yasuharu Imai, Yoshiyuki Sawai, Etsuo Niki. Levels of lipid peroxidation in human plasma and erythrocytes: comparison between fatty acids and cholesterol.
Lipids.
2007 May; 42(5):439-49. doi:
10.1007/s11745-007-3037-5. [PMID: 17476548] - Yasukazu Yoshida, Mieko Hayakawa, Yoko Habuchi, Nanako Itoh, Etsuo Niki. Evaluation of lipophilic antioxidant efficacy in vivo by the biomarkers hydroxyoctadecadienoic acid and isoprostane.
Lipids.
2007 May; 42(5):463-72. doi:
10.1007/s11745-007-3043-7. [PMID: 17476550] - Shintaro Kodai, Shigekazu Takemura, Yukiko Minamiyama, Seikan Hai, Satoshi Yamamoto, Shoji Kubo, Yasukazu Yoshida, Etsuo Niki, Shigeru Okada, Kazuhiro Hirohashi, Shigefumi Suehiro. S-allyl cysteine prevents CCl(4)-induced acute liver injury in rats.
Free radical research.
2007 Apr; 41(4):489-97. doi:
10.1080/10715760601118361. [PMID: 17454131] - Masaki Tanito, Yasukazu Yoshida, Sachiko Kaidzu, Zhi-Hua Chen, Osamu Cynshi, Kou-Ichi Jishage, Etsuo Niki, Akihiro Ohira. Acceleration of age-related changes in the retina in alpha-tocopherol transfer protein null mice fed a Vitamin E-deficient diet.
Investigative ophthalmology & visual science.
2007 Jan; 48(1):396-404. doi:
10.1167/iovs.06-0872. [PMID: 17197560] - Yasukazu Yoshida, Mieko Hayakawa, Yoko Habuchi, Etsuo Niki. Evaluation of the dietary effects of coenzyme Q in vivo by the oxidative stress marker, hydroxyoctadecadienoic acid and its stereoisomer ratio.
Biochimica et biophysica acta.
2006 Oct; 1760(10):1558-68. doi:
10.1016/j.bbagen.2006.06.007. [PMID: 16908102] - Masaki Tanito, Yasukazu Yoshida, Sachiko Kaidzu, Akihiro Ohira, Etsuo Niki. Detection of lipid peroxidation in light-exposed mouse retina assessed by oxidative stress markers, total hydroxyoctadecadienoic acid and 8-iso-prostaglandin F2alpha.
Neuroscience letters.
2006 May; 398(1-2):63-8. doi:
10.1016/j.neulet.2005.12.070. [PMID: 16442231] - Yasukazu Yoshida, Nanako Itoh, Mieko Hayakawa, Yoko Habuchi, Ruriko Inoue, Zhi-Hua Chen, Jiaofei Cao, Osamu Cynshi, Etsuo Niki. Lipid peroxidation in mice fed a choline-deficient diet as evaluated by total hydroxyoctadecadienoic acid.
Nutrition (Burbank, Los Angeles County, Calif.).
2006 Mar; 22(3):303-11. doi:
10.1016/j.nut.2005.07.020. [PMID: 16500556] - Yasukazu Yoshida, Etsuo Niki. Bio-markers of lipid peroxidation in vivo: hydroxyoctadecadienoic acid and hydroxycholesterol.
BioFactors (Oxford, England).
2006; 27(1-4):195-202. doi:
10.1002/biof.5520270117. [PMID: 17012775] - Etsuo Niki, Yasukazu Yoshida. Biomarkers for oxidative stress: measurement, validation, and application.
The journal of medical investigation : JMI.
2005 Nov; 52 Suppl(?):228-30. doi:
10.2152/jmi.52.228. [PMID: 16366503] - Yasukazu Yoshida, Nanako Itoh, Mieko Hayakawa, Rosaria Piga, Osamu Cynshi, Kou-ichi Jishage, Etsuo Niki. Lipid peroxidation induced by carbon tetrachloride and its inhibition by antioxidant as evaluated by an oxidative stress marker, HODE.
Toxicology and applied pharmacology.
2005 Oct; 208(1):87-97. doi:
10.1016/j.taap.2005.01.015. [PMID: 16164964] - Yasukazu Yoshida, Mieko Hayakawa, Etsuo Niki. Total hydroxyoctadecadienoic acid as a marker for lipid peroxidation in vivo.
BioFactors (Oxford, England).
2005; 24(1-4):7-15. doi:
10.1002/biof.5520240102. [PMID: 16403959] - Yasukazu Yoshida, Etsuo Niki. Detection of lipid peroxidation in vivo: total hydroxyoctadecadienoic acid and 7-hydroxycholesterol as oxidative stress marker.
Free radical research.
2004 Aug; 38(8):787-94. doi:
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