3-HODE + 9-HODE (BioDeep_00000003297)

 

Secondary id: BioDeep_00001871419

human metabolite Endogenous blood metabolite


代谢物信息卡片


13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomer

化学式: C18H32O3 (296.2351322)
中文名称: 13(s)-羟基-9z,11e-十八二烯酸, 13-羟基十八碳二烯酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.63%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

3-HODE + 9-HODE. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/3-hode_9-hode (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000003297). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(CCCCCC/C=C\C=C\[C@H](CCCCC)O)C(=O)O
InChI: InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1

描述信息

13-Hydroxyoctadecadienoic acid (13-HODE) (CAS: 18104-45-5), also known as 13(S)-hydroxy-9Z,11E-octadecadienoic acid or 13(S)-HODE, is the major lipoxygenation product synthesized in the body from linoleic acid. 13-HODE prevents cell adhesion to endothelial cells and can inhibit cancer metastasis. 13-HODE synthesis is enhanced by cyclic AMP. gamma-Linolenic acid, a desaturated metabolite of linoleic acid, causes substantial stimulation of 13-HODE synthesis. A fall in gamma-linolenic acid synthesis with age may be related to the age-related fall in 13-HODE formation (PMID: 9561154). 13-HODE is considered an intermediate in linoleic acid metabolism. It is generated from 13(S)-HPODE via the enzyme lipoxygenase (EC 1.13.11.12). 13-HODE has been shown to be involved in cell proliferation and differentiation in a number of systems. 13-HODE is found to be produced by prostate tumours and cell lines and researchers believe that there is a link between linoleic acid metabolism and the development or progression of prostate cancer (PMID: 9367845).

同义名列表

44 个代谢物同义名

13-Hydroxy-9,11-octadecadienoic acid, (S)-(e,Z)-isomer; (9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid; (9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid; 13-Hydroxy-9,11-octadecadienoic acid, (Z,e)-isomer; 13-Hydroxy-9,11-octadecadienoic acid, (e,Z)-isomer; (9Z,11E,13S)-13-Hydroxy-9,11-octadecadienoic acid; (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoic acid; (13S,9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid; L-13-Hydroxy-cis-9,trans-11-octadecadienoic acid; (9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate; (9Z,11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoate; 13-Hydroxy-9,11-cis,trans-octadecadienoic acid; 13-Hydroxy-9-cis-11-trans-octadecadienoic acid; 13-Hydroxy-cis-9-trans-11-octadecadienoic acid; (9Z,11E,13S)-13-Hydroxyoctadeca-9,11-dienoate; (9Z,11E)-13-Hydroxy-9,11-octadecadienoic acid; (9Z,11E,13S)-13-Hydroxyoctadecadienoic acid; 13-Hydroxy-9(Z),11(e)-octadecadienoic acid; 13S-hydroxy-9Z,11E-octadecadienoic acid; (9Z,11E)-13-Hydroxyoctadecadienoic acid; 13-Hydroxy-9Z,11E-octadecadienoic acid; 13-Hydroxy-9,11-octadecadienoic acid; 13-hydroxyoctadeca-9,11-dienoic acid; (13S)-Hydroxyoctadecadienoic acid; 13S-hydroxyoctadecadienoic acid; 13-Hydroxyoctadecadienoic acid; (13S)-Hydroxyoctadecadienoate; 13S-Hydroxyoctadecadienoate; 13-Hydroxyoctadecadienoate; FA(18:2(9Z,11E,13S-OH)); 13-Hydroxylinoleic acid; alpha-Artemisolic acid; FA(18:2(9Z,11E,13-OH)); Α-artemisolic acid; (±)-coriolic acid; (S)-Coriolic acid; (+)-Coriolic acid; (9Z,11E)-13-HODE; 13(S) HODE; 13(S)-HODE; FA 18:2;O; 13S-HODE; 13-HODE; 13-HOD



数据库引用编号

20 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

2 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(0)

PharmGKB(0)

13 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

  • Daniel Maynard, Kamel Chibani, Sonja Schmidtpott, Thorsten Seidel, Jens Spross, Andrea Viehhauser, Karl-Josef Dietz. Biochemical Characterization of 13-Lipoxygenases of Arabidopsis thaliana. International journal of molecular sciences. 2021 Sep; 22(19):. doi: 10.3390/ijms221910237. [PMID: 34638573]
  • Francesco Tinto, Anne-Sophie Archambault, Élizabeth Dumais, Volatiana Rakotoarivelo, Magdalena Kostrzewa, Cyril Martin, Pier-Luc Plante, Yves Desjardins, Mélissa Simard, Roxane Pouliot, Luciano De Petrocellis, Alessia Ligresti, Vincenzo Di Marzo, Nicolas Flamand. Synthesis and molecular targets of N-13-hydroxy-octadienoyl-ethanolamine, a novel endogenous bioactive 15-lipoxygenase-derived metabolite of N-linoleoyl-ethanolamine found in the skin and saliva. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2021 08; 1866(8):158954. doi: 10.1016/j.bbalip.2021.158954. [PMID: 33915294]
  • Zhichao Zhang, Shiva Emami, Marie Hennebelle, Rhianna K Morgan, Larry A Lerno, Carolyn M Slupsky, Pamela J Lein, Ameer Y Taha. Linoleic acid-derived 13-hydroxyoctadecadienoic acid is absorbed and incorporated into rat tissues. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2021 03; 1866(3):158870. doi: 10.1016/j.bbalip.2020.158870. [PMID: 33340768]
  • Soke Chee Kwong, Amira Hajirah Abd Jamil, Anthony Rhodes, Nur Aishah Taib, Ivy Chung. Fatty acid binding protein 7 mediates linoleic acid-induced cell death in triple negative breast cancer cells by modulating 13-HODE. Biochimie. 2020 Dec; 179(?):23-31. doi: 10.1016/j.biochi.2020.09.005. [PMID: 32931863]
  • Dominika Maciejewska, Arleta Drozd, Karolina Skonieczna-Żydecka, Marta Skórka-Majewicz, Karolina Dec, Karolina Jakubczyk, Anna Pilutin, Ewa Stachowska. Eicosanoids in Nonalcoholic Fatty Liver Disease (NAFLD) Progression. Do Serum Eicosanoids Profile Correspond with Liver Eicosanoids Content during NAFLD Development and Progression?. Molecules (Basel, Switzerland). 2020 Apr; 25(9):. doi: 10.3390/molecules25092026. [PMID: 32349225]
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  • Huan Bian, Jingjing Ma, Zhiming Geng, Ting Liu, Chong Sun, Daoying Wang, Muhan Zhang, Weimin Xu. Changes of hydroxyl-linoleic acids during Chinese-style sausage processing and their relationships with lipids oxidation. Food chemistry. 2019 Oct; 296(?):63-68. doi: 10.1016/j.foodchem.2019.05.183. [PMID: 31202307]
  • Yujin Ye, Tianfu Wu, Ting Zhang, Jie Han, Deena Habazi, Ramesh Saxena, Chandra Mohan. Elevated oxidized lipids, anti-lipid autoantibodies and oxidized lipid immune complexes in active SLE. Clinical immunology (Orlando, Fla.). 2019 08; 205(?):43-48. doi: 10.1016/j.clim.2019.05.004. [PMID: 31075396]
  • Alaleh Bayat Barooni, Mohammad Ghorbani, Vahid Salimi, Alimohammad Alimohammadi, Mohammad E Khamseh, Hamideh Akbari, Mehrnaz Imani, Mitra Nourbakhsh, Alireza Sheikhi, Farzad Izak Shirian, Maryam Ameri, Masoumeh Tavakoli-Yaraki. Up-regulation of 15-lipoxygenase enzymes and products in functional and non-functional pituitary adenomas. Lipids in health and disease. 2019 Jul; 18(1):152. doi: 10.1186/s12944-019-1089-1. [PMID: 31288808]
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  • Izabella Surowiec, Sandra Gouveia-Figueira, Judy Orikiiriza, Elisabeth Lindquist, Mari Bonde, Jimmy Magambo, Charles Muhinda, Sven Bergström, Johan Normark, Johan Trygg. The oxylipin and endocannabidome responses in acute phase Plasmodium falciparum malaria in children. Malaria journal. 2017 09; 16(1):358. doi: 10.1186/s12936-017-2001-y. [PMID: 28886714]
  • Wenliang Zhang, Wei Zhong, Qian Sun, Xinguo Sun, Zhanxiang Zhou. Hepatic overproduction of 13-HODE due to ALOX15 upregulation contributes to alcohol-induced liver injury in mice. Scientific reports. 2017 08; 7(1):8976. doi: 10.1038/s41598-017-02759-0. [PMID: 28827690]
  • Marie Hennebelle, Yurika Otoki, Jun Yang, Bruce D Hammock, Anthony J Levitt, Ameer Y Taha, Walter Swardfager. Altered soluble epoxide hydrolase-derived oxylipins in patients with seasonal major depression: An exploratory study. Psychiatry research. 2017 06; 252(?):94-101. doi: 10.1016/j.psychres.2017.02.056. [PMID: 28259037]
  • Jinhua Dong, Mototada Shichiri, Chan-I Chung, Takahiro Shibata, Koji Uchida, Yoshihisa Hagihara, Yasukazu Yoshida, Hiroshi Ueda. An open sandwich immunoassay for detection of 13(R,S)-hydroxy-9(E),11(E)-octadecadienoic acid. The Analyst. 2017 Feb; 142(5):787-793. doi: 10.1039/c6an02437h. [PMID: 28144646]
  • David C Nieman, Mary Pat Meaney, Casey S John, Kevin J Knagge, Huiyuan Chen. 9- and 13-Hydroxy-octadecadienoic acids (9+13 HODE) are inversely related to granulocyte colony stimulating factor and IL-6 in runners after 2h running. Brain, behavior, and immunity. 2016 Aug; 56(?):246-52. doi: 10.1016/j.bbi.2016.03.020. [PMID: 27018002]
  • Leland L Black, Roshni Srivastava, Trenton R Schoeb, Ray D Moore, Stephen Barnes, Janusz H Kabarowski. Cholesterol-Independent Suppression of Lymphocyte Activation, Autoimmunity, and Glomerulonephritis by Apolipoprotein A-I in Normocholesterolemic Lupus-Prone Mice. Journal of immunology (Baltimore, Md. : 1950). 2015 Nov; 195(10):4685-98. doi: 10.4049/jimmunol.1500806. [PMID: 26466956]
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