Hepoxilin A3 (BioDeep_00000014526)

 

Secondary id: BioDeep_00000594397

human metabolite Endogenous blood metabolite


代谢物信息卡片


(5Z,9E)-8-hydroxy-10-[(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid

化学式: C20H32O4 (336.2300472)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.11%

分子结构信息

SMILES: C(CCC/C=C\CC(O)/C=C/[C@@H]1O[C@H]1C/C=C\CCCCC)(=O)O
InChI: InChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/b9-7-,10-6-,16-15+/t17?,18-,19+/m0/s1

描述信息

Hepoxilin A3 is an electrophilic eicosanoids synthesized during arachidonic acid oxidative metabolism, which can participate in the Michael addition reaction with glutathione (GSH, a major cellular antioxidant) catalyzed by the GSH-S-transferase (GST) family. GSH-adducts have been observed with molecules synthesized through the 12-lipoxygenase pathway. (PMID 12432937). Hepoxilins have biological actions that appear to have, as their basis, changes in intracellular concentrations of ions including calcium and potassium ions as well as changes in second messenger systems. Recent evidence suggests that the biological actions of the hepoxilins may be receptor-mediated as indicated from data showing the existence of hepoxilin-specific binding proteins in the human neutrophils. Such evidence also implicates the association of G-proteins both in hepoxilin-binding as well as in hepoxilin action. (PMID 7947989).
Hepoxilin A3 is an electrophilic eicosanoids synthesized during arachidonic acid oxidative metabolism, which can participate in the Michael addition reaction with glutathione (GSH, a major cellular antioxidant) catalyzed by the GSH-S-transferase (GST) family. GSH-adducts have been observed with molecules synthesized through the 12-lipoxygenase pathway. (PMID 12432937)

同义名列表

23 个代谢物同义名

(5Z,9E)-8-hydroxy-10-[(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid; (5Z,9E)-8-Hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoic acid; (5Z,9E)-8-Hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoate; (5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyeicosa-5,9,14-trienoic acid; (5Z,9E,14Z)-(8xi,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoic Acid; (5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoic acid; (5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyeicosa-5,9,14-trienoate; (5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoate; (5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoic acid; (5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoate; (5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoate; 8-hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoic acid; 8-Hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoate; 8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acid; 8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoate; 11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoate; Hexophilin a3; hepoxilin A3; Hepoxilin a; FA 20:4;O2; HXA3 CPD; 8-EH-2; HXA3



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(0)

PlantCyc(0)

代谢反应

66 个相关的代谢反应过程信息。

Reactome(65)

BioCyc(0)

WikiPathways(1)

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

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

  • Walter Adams, Rudra Bhowmick, Elsa N Bou Ghanem, Kristin Wade, Mikhail Shchepetov, Jeffrey N Weiser, Beth A McCormick, Rodney K Tweten, John M Leong. Pneumolysin Induces 12-Lipoxygenase-Dependent Neutrophil Migration during Streptococcus pneumoniae Infection. Journal of immunology (Baltimore, Md. : 1950). 2020 01; 204(1):101-111. doi: 10.4049/jimmunol.1800748. [PMID: 31776202]
  • Ann M Gregus, Matthew W Buczynski, Darren S Dumlao, Paul C Norris, Ganesha Rai, Anton Simeonov, David J Maloney, Ajit Jadhav, Qinghao Xu, Spencer C Wei, Bethany L Fitzsimmons, Edward A Dennis, Tony L Yaksh. Inhibition of spinal 15-LOX-1 attenuates TLR4-dependent, nonsteroidal anti-inflammatory drug-unresponsive hyperalgesia in male rats. Pain. 2018 Dec; 159(12):2620-2629. doi: 10.1097/j.pain.0000000000001373. [PMID: 30130298]
  • Jung-Ung An, Yong-Seok Song, Kyoung-Rok Kim, Yoon-Joo Ko, Do-Young Yoon, Deok-Kun Oh. Biotransformation of polyunsaturated fatty acids to bioactive hepoxilins and trioxilins by microbial enzymes. Nature communications. 2018 01; 9(1):128. doi: 10.1038/s41467-017-02543-8. [PMID: 29317615]
  • David N Douda, Hartmut Grasemann, Cecil Pace-Asciak, Nades Palaniyar. A lipid mediator hepoxilin A3 is a natural inducer of neutrophil extracellular traps in human neutrophils. Mediators of inflammation. 2015; 2015(?):520871. doi: 10.1155/2015/520871. [PMID: 25784781]
  • S A Kubala, S U Patil, W G Shreffler, B P Hurley. Pathogen induced chemo-attractant hepoxilin A3 drives neutrophils, but not eosinophils across epithelial barriers. Prostaglandins & other lipid mediators. 2014 Jan; 108(?):1-8. doi: 10.1016/j.prostaglandins.2013.11.001. [PMID: 24315875]
  • David L Tamang, Waheed Pirzai, Gregory P Priebe, David C Traficante, Gerald B Pier, John R Falck, Christophe Morisseau, Bruce D Hammock, Beth A McCormick, Karsten Gronert, Bryan P Hurley. Hepoxilin A(3) facilitates neutrophilic breach of lipoxygenase-expressing airway epithelial barriers. Journal of immunology (Baltimore, Md. : 1950). 2012 Nov; 189(10):4960-9. doi: 10.4049/jimmunol.1201922. [PMID: 23045615]
  • Ann M Gregus, Suzanne Doolen, Darren S Dumlao, Matthew W Buczynski, Toshifumi Takasusuki, Bethany L Fitzsimmons, Xiao-Ying Hua, Bradley K Taylor, Edward A Dennis, Tony L Yaksh. Spinal 12-lipoxygenase-derived hepoxilin A3 contributes to inflammatory hyperalgesia via activation of TRPV1 and TRPA1 receptors. Proceedings of the National Academy of Sciences of the United States of America. 2012 Apr; 109(17):6721-6. doi: 10.1073/pnas.1110460109. [PMID: 22493235]
  • Maria-Patapia Zafiriou, Laura Cecilia Zelarayan, Claudia Noack, Anke Renger, Santosh Nigam, Athanassia Siafaka-Kapadai. Hepoxilin A(3) protects β-cells from apoptosis in contrast to its precursor, 12-hydroperoxyeicosatetraenoic acid. Biochimica et biophysica acta. 2011 Jun; 1811(6):361-9. doi: 10.1016/j.bbalip.2011.03.002. [PMID: 21420506]
  • Annette Cronin, Martina Decker, Michael Arand. Mammalian soluble epoxide hydrolase is identical to liver hepoxilin hydrolase. Journal of lipid research. 2011 Apr; 52(4):712-9. doi: 10.1194/jlr.m009639. [PMID: 21217101]
  • Santosh Nigam, Maria-Patapia Zafiriou. Hepoxilin A3 synthase. Biochemical and biophysical research communications. 2005 Dec; 338(1):161-8. doi: 10.1016/j.bbrc.2005.09.065. [PMID: 16198304]
  • M M Wang, D Reynaud, C R Pace-Asciak. In vivo stimulation of 12(S)-lipoxygenase in the rat skin by bradykinin and platelet activating factor: formation of 12(S)-HETE and hepoxilins, and actions on vascular permeability. Biochimica et biophysica acta. 1999 Jan; 1436(3):354-62. doi: 10.1016/s0005-2760(98)00128-3. [PMID: 9989266]
  • C R Pace-Asciak, D Reynaud, P Demin. Mechanistic aspects of hepoxilin biosynthesis. Journal of lipid mediators and cell signalling. 1995 Oct; 12(2-3):307-11. doi: 10.1016/0929-7855(95)00036-p. [PMID: 8777574]
  • A Margalit, Y Sofer, S Grossman, D Reynaud, C R Pace-Asciak, A A Livne. Hepoxilin A3 is the endogenous lipid mediator opposing hypotonic swelling of intact human platelets. Proceedings of the National Academy of Sciences of the United States of America. 1993 Apr; 90(7):2589-92. doi: 10.1073/pnas.90.7.2589. [PMID: 8464865]
  • C R Pace-Asciak, S Nigam. Hepoxilins modulate second messenger systems in the human neutrophil. Advances in experimental medicine and biology. 1991; 314(?):133-9. doi: 10.1007/978-1-4684-6024-7_8. [PMID: 1818483]
  • C R Pace-Asciak, J M Martin, S P Lee. Appearance of prostaglandins, thromboxane B2, and hepoxilin A3 in the circulation of the normal and diabetic (BB) rat after arachidonic acid administration--correlation with plasma insulin. Biochemistry and cell biology = Biochimie et biologie cellulaire. 1988 Aug; 66(8):901-9. doi: 10.1139/o88-102. [PMID: 3143376]
  • C R Pace-Asciak, S P Lee, J M Martin. In vivo formation of hepoxilin A3 in the rat. Biochemical and biophysical research communications. 1987 Sep; 147(3):881-4. doi: 10.1016/s0006-291x(87)80152-3. [PMID: 3117060]
  • C R Pace-Asciak, J Klein, S P Speilberg. Epoxide hydratase assay in human platelets using hepoxilin A3 as a lipid substrate. Biochimica et biophysica acta. 1986 Feb; 875(2):406-9. doi: 10.1016/0005-2760(86)90193-1. [PMID: 3942774]
  • C R Pace-Asciak, J M Martin, E J Corey. Hepoxilins, potential endogenous mediators of insulin release. Progress in lipid research. 1986; 25(1-4):625-8. doi: 10.1016/0163-7827(86)90127-x. [PMID: 3321096]