Resolvin D5 (BioDeep_00000019031)

   

human metabolite Endogenous


代谢物信息卡片


(5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid

化学式: C22H32O4 (360.2300472)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC/C=C\C[C@@H](/C=C/C=C\C/C=C\C=C\[C@H](C/C=C\CCC(=O)O)O)O
InChI: InChI=1S/C22H32O4/c1-2-3-10-15-20(23)16-11-7-5-4-6-8-12-17-21(24)18-13-9-14-19-22(25)26/h3,5-8,10-13,16-18,20-21,23-24H,2,4,9,14-15,19H2,1H3,(H,25,26)/b7-5-,8-6-,10-3-,16-11+,17-12+,18-13-/t20-,21+/m0/s1

描述信息

Resolvin D5 is an autacoid resolvin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. The bioactive local mediators, or autacoids, that require enzymatic generation from the omega-3 essential fatty acid EPA were first identified in resolving inflammatory exudates in vivo and carry potent stereoselective biological actions. Resolvins of the E (RvE) series are derived from eicosapentaenoic acid (EPA). Those derived from docosahexaenoic acid (DHA) were termed resolvins of the D series, for example resolvin D1 (RvD1).Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The term resolvins (resolution-phase interaction products) was first introduced to signify that these new structures were endogenous mediators, biosynthesized in the resolution phase of inflammatory exudates, possessing very potent anti-inflammatory and immunoregulatory actions. These actions include reducing neutrophil traffic, regulating cytokine and reactive oxygen species, and lowering the magnitude of the response. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimers disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225) [HMDB]
Resolvin D5 is an autacoid resolvin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. The bioactive local mediators, or autacoids, that require enzymatic generation from the omega-3 essential fatty acid EPA were first identified in resolving inflammatory exudates in vivo and carry potent stereoselective biological actions. Resolvins of the E (RvE) series are derived from eicosapentaenoic acid (EPA). Those derived from docosahexaenoic acid (DHA) were termed resolvins of the D series, for example resolvin D1 (RvD1).Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The term resolvins (resolution-phase interaction products) was first introduced to signify that these new structures were endogenous mediators, biosynthesized in the resolution phase of inflammatory exudates, possessing very potent anti-inflammatory and immunoregulatory actions. These actions include reducing neutrophil traffic, regulating cytokine and reactive oxygen species, and lowering the magnitude of the response. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimers disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225).

同义名列表

10 个代谢物同义名

(5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid; (5Z,7S,8E,10Z,13Z,15Z,17S,19Z)-7,17-Dihydroxydocosahexaenoic acid; (5Z,7S,8E,10Z,13Z,15Z,17S,19Z)-7,17-Dihydroxydocosahexaenoate; 7S,17S-Dihydroxy-docosa-5Z,8E,10Z,13Z,15E,19Z-hexaenoic acid; 7S,17S-Dihydroxy-5Z,8E,10Z,13Z,15E,19Z-docosahexaenoic acid; 7S,17S-Dihydroxy-docosa-5Z,8E,10Z,13Z,15E,19Z-hexaenoate; 7S,17S-Dihydroxy-5Z,8E,10Z,13Z,15E,19Z-docosahexaenoate; RVD5 Resolvin; Resolvin D5; RVD5



数据库引用编号

8 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(3)

BioCyc(0)

PlantCyc(0)

代谢反应

5 个相关的代谢反应过程信息。

Reactome(5)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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

  • Jin Lee, Hyun-Ah Park, Kyung-Chul Shin, Jin-Byung Park, Deok-Kun Oh. Efficient biotransformation of docosahexaenoic acid-rich oils into the lipid mediator resolvin D5 by cells expressing 15S-lipoxygenase using a bioreactor. Bioresource technology. 2023 Sep; ?(?):129750. doi: 10.1016/j.biortech.2023.129750. [PMID: 37717704]
  • Darciane F Baggio, Fernanda M R da Luz, Raphael V Lopes, Luiz E N Ferreira, Erika I Araya, Juliana G Chichorro. Sex Dimorphism in Resolvin D5-induced Analgesia in Rat Models of Trigeminal Pain. The journal of pain. 2023 05; 24(5):717-729. doi: 10.1016/j.jpain.2022.12.013. [PMID: 36584931]
  • Gabriel A Aguirre, Michelle R Goulart, Jesmond Dalli, Hemant M Kocher. Arachidonate 15-lipoxygenase-mediated production of Resolvin D5n-3 DPA abrogates pancreatic stellate cell-induced cancer cell invasion. Frontiers in immunology. 2023; 14(?):1248547. doi: 10.3389/fimmu.2023.1248547. [PMID: 38035115]
  • Felipe Fagundes Leão, Ana Paula Farias Waltrick, Waldiceu Aparecido Verri, Joice Maria da Cunha, Janaina Menezes Zanoveli. Resolvin D5 disrupts anxious- and depressive-like behaviors in a type 1 diabetes mellitus animal model. Naunyn-Schmiedeberg's archives of pharmacology. 2022 Jul; ?(?):. doi: 10.1007/s00210-022-02274-8. [PMID: 35852551]
  • Malwina Mainka, Sven George, Carlo Angioni, Roland Ebert, Tamara Goebel, Nadja Kampschulte, Andre Krommes, Andreas Weigert, Dominique Thomas, Nils Helge Schebb, Dieter Steinhilber, Astrid Stefanie Kahnt. On the biosynthesis of specialized pro-resolving mediators in human neutrophils and the influence of cell integrity. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2022 03; 1867(3):159093. doi: 10.1016/j.bbalip.2021.159093. [PMID: 34942381]
  • Ellen C Keeley, Han J Li, Christopher R Cogle, Eileen M Handberg, C Noel Bairey Merz, Carl J Pepine. Specialized Proresolving Mediators in Symptomatic Women With Coronary Microvascular Dysfunction (from the Women's Ischemia Trial to Reduce Events in Nonobstructive CAD [WARRIOR] Trial). The American journal of cardiology. 2022 01; 162(?):1-5. doi: 10.1016/j.amjcard.2021.09.015. [PMID: 34728061]
  • Hirotaka Yamada, Jun Saegusa, Sho Sendo, Yo Ueda, Takaichi Okano, Masakazu Shinohara, Akio Morinobu. Effect of resolvin D5 on T cell differentiation and osteoclastogenesis analyzed by lipid mediator profiling in the experimental arthritis. Scientific reports. 2021 08; 11(1):17312. doi: 10.1038/s41598-021-96530-1. [PMID: 34453072]
  • Eluisa Perna, Javier Aguilera-Lizarraga, Morgane V Florens, Piyush Jain, Stavroula A Theofanous, Nikita Hanning, Joris G De Man, Maya Berg, Benedicte De Winter, Yeranddy A Alpizar, Karel Talavera, Pieter Vanden Berghe, Mira Wouters, Guy Boeckxstaens. Effect of resolvins on sensitisation of TRPV1 and visceral hypersensitivity in IBS. Gut. 2021 07; 70(7):1275-1286. doi: 10.1136/gutjnl-2020-321530. [PMID: 33023902]
  • Steven C Perry, Chakrapani Kalyanaraman, Benjamin E Tourdot, William S Conrad, Oluwayomi Akinkugbe, John Cody Freedman, Michael Holinstat, Matthew P Jacobson, Theodore R Holman. 15-Lipoxygenase-1 biosynthesis of 7S,14S-diHDHA implicates 15-lipoxygenase-2 in biosynthesis of resolvin D5. Journal of lipid research. 2020 07; 61(7):1087-1103. doi: 10.1194/jlr.ra120000777. [PMID: 32404334]
  • Hyun-Woo Chun, Jintak Lee, Thu-Huyen Pham, Jiyon Lee, Jae-Hwan Yoon, Jin Lee, Deok-Kun Oh, Jaewook Oh, Do-Young Yoon. Resolvin D5, a Lipid Mediator, Inhibits Production of Interleukin-6 and CCL5 Via the ERK-NF-κB Signaling Pathway in Lipopolysaccharide-Stimulated THP-1 Cells. Journal of microbiology and biotechnology. 2020 Jan; 30(1):85-92. doi: 10.4014/jmb.1907.07033. [PMID: 31693828]
  • Magdalena B Flak, Romain A Colas, Estefanía Muñoz-Atienza, Michael A Curtis, Jesmond Dalli, Costantino Pitzalis. Inflammatory arthritis disrupts gut resolution mechanisms, promoting barrier breakdown by Porphyromonas gingivalis. JCI insight. 2019 07; 4(13):. doi: 10.1172/jci.insight.125191. [PMID: 31292292]
  • Alexander V Sorokin, Paul C Norris, Justin T English, Amit K Dey, Abhishek Chaturvedi, Yvonne Baumer, Joanna Silverman, Martin P Playford, Charles N Serhan, Nehal N Mehta. Identification of proresolving and inflammatory lipid mediators in human psoriasis. Journal of clinical lipidology. 2018 Jul; 12(4):1047-1060. doi: 10.1016/j.jacl.2018.03.091. [PMID: 29730187]
  • Romain A Colas, Anthony W Ashton, Shankar Mukherjee, Jesmond Dalli, Oscar B Akide-Ndunge, Huan Huang, Mahalia S Desruisseaux, Fangxia Guan, Linda A Jelicks, Fabiane Matos Dos Santos, Jyothi Nagajyothi, Michael A Zingman, Jinet Reyes, Louis M Weiss, Charles N Serhan, Herbert B Tanowitz. Trypanosoma cruzi Produces the Specialized Proresolving Mediators Resolvin D1, Resolvin D5, and Resolvin E2. Infection and immunity. 2018 04; 86(4):. doi: 10.1128/iai.00688-17. [PMID: 29358332]
  • Ganesh V Halade, Anela Dorbane, Kevin A Ingle, Vasundhara Kain, Jean-Marie Schmitter, Boutayna Rhourri-Frih. Comprehensive targeted and non-targeted lipidomics analyses in failing and non-failing heart. Analytical and bioanalytical chemistry. 2018 Mar; 410(7):1965-1976. doi: 10.1007/s00216-018-0863-7. [PMID: 29411084]
  • Florence Riché, Benjamin G Chousterman, Patrice Valleur, Alexandre Mebazaa, Jean-Marie Launay, Etienne Gayat. Protracted immune disorders at one year after ICU discharge in patients with septic shock. Critical care (London, England). 2018 Feb; 22(1):42. doi: 10.1186/s13054-017-1934-4. [PMID: 29467023]
  • Oliver Werz, Jana Gerstmeier, Stephania Libreros, Xavier De la Rosa, Markus Werner, Paul C Norris, Nan Chiang, Charles N Serhan. Human macrophages differentially produce specific resolvin or leukotriene signals that depend on bacterial pathogenicity. Nature communications. 2018 01; 9(1):59. doi: 10.1038/s41467-017-02538-5. [PMID: 29302056]
  • Luis Alonso Diaz, Norman H Altman, Wasif N Khan, Charles N Serhan, Becky Adkins. Specialized Proresolving Mediators Rescue Infant Mice from Lethal Citrobacter rodentium Infection and Promote Immunity against Reinfection. Infection and immunity. 2017 10; 85(10):. doi: 10.1128/iai.00464-17. [PMID: 28694292]
  • Thomas Gobbetti, Jesmond Dalli, Romain A Colas, Donata Federici Canova, Marius Aursnes, Delphine Bonnet, Laurent Alric, Nathalie Vergnolle, Celine Deraison, Trond V Hansen, Charles N Serhan, Mauro Perretti. Protectin D1n-3 DPA and resolvin D5n-3 DPA are effectors of intestinal protection. Proceedings of the National Academy of Sciences of the United States of America. 2017 04; 114(15):3963-3968. doi: 10.1073/pnas.1617290114. [PMID: 28356517]