5-HEPE (BioDeep_00000018512)
human metabolite Endogenous blood metabolite natural product
代谢物信息卡片
化学式: C20H30O3 (318.2195)
中文名称: 5(S)-羟化二十烷四烯酸
谱图信息:
最多检出来源 Homo sapiens(blood) 41.97%
Last reviewed on 2024-09-14.
Cite this Page
5-HEPE. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/5-hepe (retrieved
2025-02-03) (BioDeep RN: BioDeep_00000018512). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(CCCC(=O)O)O
InChI: InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h3-4,6-7,9-10,12-14,16,19,21H,2,5,8,11,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-14+
描述信息
5-HEPE is a major eicosanoid formed from eicosapentaenoic acid (EPA). 5-HEPE is produced in human neutrophils. The eicosanoids are a diverse family of molecules that have powerful effects on cell function. They are best known as intercellular messengers, having autocrine and paracrine effects following their secretion from the cells that synthesize them. The diversity of possible products that can be synthesized from eicosatrienoic acid is due, in part to the variety of enzymes that can act on it. Studies have placed many, but not all, of these enzymes at or inside the nucleus. In some cases, the nuclear import or export of eicosatrienoic acid-processing enzymes is highly regulated. Furthermore, nuclear receptors that are activated by specific eicosanoids are known to exist. (PMID: 8847485, 15896193) [HMDB]
5-HEPE is a major eicosanoid formed from eicosapentaenoic acid (EPA). 5-HEPE is produced in human neutrophils. The eicosanoids are a diverse family of molecules that have powerful effects on cell function. They are best known as intercellular messengers, having autocrine and paracrine effects following their secretion from the cells that synthesize them. The diversity of possible products that can be synthesized from eicosatrienoic acid is due, in part to the variety of enzymes that can act on it. Studies have placed many, but not all, of these enzymes at or inside the nucleus. In some cases, the nuclear import or export of eicosatrienoic acid-processing enzymes is highly regulated. Furthermore, nuclear receptors that are activated by specific eicosanoids are known to exist. (PMID: 8847485, 15896193).
同义名列表
14 个代谢物同义名
(6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoic acid; (+/-)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid; (+-)-5-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid; (+/-)-5-hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoate; (+-)-5-Hydroxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoate; 5-Hydroxy-6,8,11,14,17-eicosapentaenoic acid; 5-hydroxyicosa-6,8,11,14,17-pentaenoic acid; 5-Hydroxy-6,8,11,14,17-eicosapentaenoate; 5-Hydroxyeicosapentaenoic acid; 5-Hydroxyeicosapentaenoate; (+/-)-5-HEPE; (+-)-5-HEPE; 5-HEPE; 5 HEPE
数据库引用编号
10 个数据库交叉引用编号
- ChEBI: CHEBI:72801
- PubChem: 6439678
- PubChem: 1766
- HMDB: HMDB0005081
- foodb: FDB023620
- chemspider: 4944072
- CAS: 92008-51-0
- PMhub: MS000008761
- RefMet: 5-HEPE
- LOTUS: LTS0204626
分类词条
相关代谢途径
Reactome(4)
BioCyc(0)
PlantCyc(0)
代谢反应
52 个相关的代谢反应过程信息。
Reactome(52)
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
H+ + LTHSOL + Oxygen + TPNH ⟶ 7-dehydroCHOL + H2O + TPN
- Biosynthesis of specialized proresolving mediators (SPMs):
18(R)-HEPE + Oxygen ⟶ 18(R)-RvE3
- Biosynthesis of electrophilic ?-3 PUFA oxo-derivatives:
EPA + Oxygen ⟶ 5-HEPE
- Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of lipids:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
DHA + Oxygen ⟶ 17-HDHA
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
DHA + Oxygen ⟶ 17-HDHA
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
DHA + Oxygen ⟶ 17-HDHA
- Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Metabolism of lipids:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Biosynthesis of specialized proresolving mediators (SPMs):
18(R)-HEPE + Oxygen ⟶ 18(R)-RvE3
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
EPA + Oxygen ⟶ 5-HEPE
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Biosynthesis of specialized proresolving mediators (SPMs):
18(R)-HpEPE + GSH ⟶ 18(R)-HEPE + GSSG + H2O
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
EPA + Oxygen ⟶ 5-HEPE
- Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
DHA + Oxygen ⟶ 17-HDHA
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
DHA + Oxygen ⟶ 17-HDHA
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
H+ + LTHSOL + Oxygen + TPNH ⟶ 7-dehydroCHOL + H2O + TPN
- Biosynthesis of specialized proresolving mediators (SPMs):
18(R)-HEPE + Oxygen ⟶ 18(R)-RvE3
- Biosynthesis of electrophilic ?-3 PUFA oxo-derivatives:
EPA + Oxygen ⟶ 5-HEPE
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
DHA + Oxygen ⟶ 17-HDHA
- Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Metabolism of lipids:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
DHA + Oxygen ⟶ 17-HDHA
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Biosynthesis of specialized proresolving mediators (SPMs):
13(S),14(S)-epoxy-DHA + GSH ⟶ (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoic acid
- Biosynthesis of electrophilic ?-3 PUFA oxo-derivatives:
DHA + Oxygen ⟶ 17-HDHA
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Biosynthesis of specialized proresolving mediators (SPMs):
DHA + Oxygen ⟶ 17-HDHA
- Biosynthesis of electrophilic -3 PUFA oxo-derivatives:
DHA + Oxygen ⟶ 17-HDHA
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
11 个相关的物种来源信息
- 33849 - Bacillariophyceae: LTS0204626
- 2836 - Bacillariophyta: LTS0204626
- 33836 - Coscinodiscophyceae: LTS0204626
- 2759 - Eukaryota: LTS0204626
- 9606 - Homo sapiens: -
- 589449 - Mediophyceae: LTS0204626
- 2696291 - Ochrophyta: LTS0204626
- 2842 - Skeletonema: LTS0204626
- 267567 - Skeletonema marinoi: 10.1038/S41396-018-0094-0
- 267567 - Skeletonema marinoi: LTS0204626
- 33848 - Skeletonemataceae: LTS0204626
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。
亚细胞结构定位 | 关联基因列表 |
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文献列表
- Misato Kida, Tatsuro Nakamura, Takahisa Murata. A novel eicosapentaenoic acid-derived anti-inflammatory lipid mediator 5,6-DiHETE is abundant in blue back fish intestines.
Journal of food science.
2020 Jul; 85(7):1983-1987. doi:
10.1111/1750-3841.15179
. [PMID: 32572984] - Chunjiong Wang, Wenli Liu, Liu Yao, Xuejiao Zhang, Xu Zhang, Chenji Ye, Hongfeng Jiang, Jinlong He, Yi Zhu, Ding Ai. Hydroxyeicosapentaenoic acids and epoxyeicosatetraenoic acids attenuate early occurrence of nonalcoholic fatty liver disease.
British journal of pharmacology.
2017 Jul; 174(14):2358-2372. doi:
10.1111/bph.13844
. [PMID: 28471490] - Jan Philipp Schuchardt, Simone Schmidt, Gaby Kressel, Hua Dong, Ina Willenberg, Bruce D Hammock, Andreas Hahn, Nils Helge Schebb. Comparison of free serum oxylipin concentrations in hyper- vs. normolipidemic men.
Prostaglandins, leukotrienes, and essential fatty acids.
2013 Jul; 89(1):19-29. doi:
10.1016/j.plefa.2013.04.001
. [PMID: 23694766] - Charles B Stephensen, Patrice Armstrong, John W Newman, Theresa L Pedersen, Jillian Legault, Gertrud U Schuster, Darshan Kelley, Susanna Vikman, Jaana Hartiala, Rami Nassir, Michael F Seldin, Hooman Allayee. ALOX5 gene variants affect eicosanoid production and response to fish oil supplementation.
Journal of lipid research.
2011 May; 52(5):991-1003. doi:
10.1194/jlr.p012864
. [PMID: 21296957]