Hepoxilin B3 (BioDeep_00000010157)

 

Secondary id: BioDeep_00001883288

human metabolite Endogenous natural product


代谢物信息卡片


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

化学式: C20H32O4 (336.2300472)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.24%

分子结构信息

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

描述信息

Hepoxilin B3 is a normal human epidermis eicosanoid. Hepoxilin B3 is dramatically elevated in psoriatic lesions. The primary biological action of the hepoxilins appears to relate to their ability to release calcium from intracellular stores through a receptor-mediated action. The receptor is intracellular, and appears to be G-protein coupled. The conversion of hepoxilin into its omega-hydroxy catabolite has recently been demonstrated through the action of an omega-hydroxylase. This enzyme is different from that which oxidizes leukotriene B4, as the former activity is lost when the cell is disrupted, while leukotriene B4-catabolic activity is recovered in both the intact and disrupted cell. Additionally, hepoxilin catabolism is inhibited by CCCP, a mitochondrial uncoupler, while leukotriene catabolism is unaffected. As hepoxilins cause the translocation of calcium from intracellular stores in the endoplasmic reticulum to the mitochondria, it is speculated that hepoxilin omega-oxidation takes place in the mitochondria, and the omega-oxidation product facilitates accumulation of the elevated cytosolic calcium by the mitochondria. (PMID 10692117, 11851887, 10086189) [HMDB]
Hepoxilin B3 is a normal human epidermis eicosanoid. Hepoxilin B3 is dramatically elevated in psoriatic lesions. The primary biological action of the hepoxilins appears to relate to their ability to release calcium from intracellular stores through a receptor-mediated action. The receptor is intracellular, and appears to be G-protein coupled. The conversion of hepoxilin into its omega-hydroxy catabolite has recently been demonstrated through the action of an omega-hydroxylase. This enzyme is different from that which oxidizes leukotriene B4, as the former activity is lost when the cell is disrupted, while leukotriene B4-catabolic activity is recovered in both the intact and disrupted cell. Additionally, hepoxilin catabolism is inhibited by CCCP, a mitochondrial uncoupler, while leukotriene catabolism is unaffected. As hepoxilins cause the translocation of calcium from intracellular stores in the endoplasmic reticulum to the mitochondria, it is speculated that hepoxilin omega-oxidation takes place in the mitochondria, and the omega-oxidation product facilitates accumulation of the elevated cytosolic calcium by the mitochondria. (PMID 10692117, 11851887, 10086189).

同义名列表

25 个代谢物同义名

(5Z,8Z)-10-hydroxy-10-[(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,8-dienoic acid; (5Z,8Z)-10-Hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid; (5Z,8Z)-10-hydroxy-10-[(2R,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoic acid; (5Z,8Z)-10-Hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoate; (5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acid; (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acid; (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoicacid; (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acid; (5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acid; (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoicacid; (5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoate; (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoate; (5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoate; (5Z,8Z,14Z)-(11S,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoate; 10-Hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid; 10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid; 10-Hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoate; 10-Hydroxy-11,12-epoxyeicosa-5,8,14-trienoic acid; Erythro-hepoxilin b3; Threo-hepoxilin b3; hepoxilin B3; Hepoxilin b; FA 20:4;O2; EPHETA; HXB3



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

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BioCyc(0)

PlantCyc(0)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

8 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

  • 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]
  • M M Wang, P M Demin, C R Pace-Asciak. Stereoselective actions of hepoxilins A3 and B3 and their cyclopropane analogs (HxdeltaA3 and HxdeltaB3) on bradykinin and PAF-evoked potentiation of vascular leakage in rat skin. General pharmacology. 1999 Nov; 33(5):377-82. doi: 10.1016/s0306-3623(99)00032-4. [PMID: 10553878]
  • D Reynaud, M Ali, P Demin, C R Pace-Asciak. Formation of 14,15-hepoxilins of the A(3) and B(3) series through a 15-lipoxygenase and hydroperoxide isomerase present in garlic roots. The Journal of biological chemistry. 1999 Oct; 274(40):28213-8. doi: 10.1074/jbc.274.40.28213. [PMID: 10497175]
  • 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]
  • M F Moghaddam, W H Gerwick, D L Ballantine. Discovery of the mammalian insulin release modulator, hepoxilin B3, from the tropical red algae Platysiphonia miniata and Cottoniella filamentosa. The Journal of biological chemistry. 1990 Apr; 265(11):6126-30. doi: . [PMID: 2180942]
  • 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]