5(S)-Hydroperoxyeicosatetraenoic acid (BioDeep_00000004019)

 

Secondary id: BioDeep_00000014606, BioDeep_00000409876

human metabolite Endogenous


代谢物信息卡片


(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid

化学式: C20H32O4 (336.23)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(otcml) 16.85%

分子结构信息

SMILES: C(/C=C\C=C\[C@@H](OO)CCCC(=O)O)/C=C\C/C=C\CCCCC
InChI: InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1

描述信息

5(S)-Hydroperoxyeicosatetraenoic acid is a lipid hydroperoxide precursor of leukotrienes. The first step of biosynthesis of leukotrienes is conversion of arachidonic acid into 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid [5(S)-HpETE] by 5- lipoxygenases (5-LOX). Lipid hydroperoxides undergo homolytic decomposition into bifunctional electrophiles, which react with DNA bases to form DNA adducts. These DNA modifications are proposed to be involved in the etiology of cancer, cardiovascular disease, and neurodegeneration. 5-LOX, the enzyme responsible for the formation of 5(S)-HpETE in vivo, is expressed primarily in leukocytes, including monocytes and macrophages. Studies have implicated the 5-LOX pathway as an important mediator in the pathology of atherosclerosis. (PMID: 15777099). Endogenously generated 5-hydroperoxyeicosatetraenoic acid is the preferred substrate for human leukocyte leukotriene A4 synthase activity. Thus, the arachidonic acid moiety is preferentially converted to LTA4 in a concerted reaction without dissociation of a 5-HPETE intermediate. (PMID: 3036580).
5(S)-Hydroperoxyeicosatetraenoic acid is a lipid hydroperoxide precursor of leukotrienes. The first step of biosynthesis of leukotrienes is conversion of arachidonic acid into 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid [5(S)-HpETE] by 5- lipoxygenases (5-LOX). Lipid hydroperoxides undergo homolytic decomposition into bifunctional electrophiles, which react with DNA bases to form DNA adducts. These DNA modifications are proposed to be involved in the etiology of cancer, cardiovascular disease, and neurodegeneration.

同义名列表

30 个代谢物同义名

(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid; (5S,6E,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid; (5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acid; (6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate; 5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate (5-HPETE); (5S,6E,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate; 5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acid; (5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoate; 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid; 5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoate; 5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid; cis,trans-5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid; 5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acid; 5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate; 5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-icosatetraenoic acid; 5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate; 5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-eicosatetraenoate; 5S-hydroperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acid; 5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-icosatetraenoate; 6,8,11,14-Eicosatetraenoic acid 5-hydroperoxide; 5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid; 5-hydroperoxyicosa-6,8,11,14-tetraenoic acid; 5(S)-Hydroperoxyeicosatetraenoic acid; 5(S)-Hydroperoxyeicosatetraenoate; Arachidonic acid 5-hydroperoxide; (S)-5-HPETE; 5(S)-HPETE; FA 20:4;O2; 5S-HpETE; 5-HpETE



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

86 个相关的代谢反应过程信息。

Reactome(80)

BioCyc(0)

WikiPathways(5)

Plant Reactome(0)

INOH(1)

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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ALB, ALOX5, CNR1, CNR2, CYP1A1, CYP2S1, CYP3A4, LTA4H, RAF1
Peripheral membrane protein 4 ALOX15, ALOX5, CYP1A1, CYP2S1
Endoplasmic reticulum membrane 4 CYP1A1, CYP1A2, CYP2S1, CYP3A4
Nucleus 6 ALB, LTA4H, MPO, PLCZ1, PPARA, RAF1
cytosol 6 ALB, ALOX15, ALOX5, LTA4H, PLCZ1, RAF1
dendrite 1 CNR2
centrosome 1 ALB
nucleoplasm 6 ALOX5, LTA4H, MPO, OLR1, PLCZ1, PPARA
Cell membrane 6 ALOX15, C5AR1, CNR1, ITGAM, OLR1, RAF1
Lipid-anchor 1 OLR1
Cell projection, axon 1 CNR1
Multi-pass membrane protein 2 C5AR1, CNR1
cell surface 1 ITGAM
glutamatergic synapse 1 CNR1
Golgi apparatus 3 ALB, ATRN, RAF1
growth cone 1 CNR1
mitochondrial inner membrane 1 CYP1A1
presynaptic membrane 1 CNR1
Cytoplasm, cytosol 2 ALOX15, ALOX5
Lysosome 1 MPO
Presynapse 1 CNR1
plasma membrane 9 ALOX15, ATRN, C5AR1, CNR1, CNR2, IGHE, ITGAM, OLR1, RAF1
Membrane 5 ALOX15, CYP2S1, CYP3A4, ITGAM, OLR1
axon 1 CNR1
basolateral plasma membrane 1 C5AR1
extracellular exosome 5 ALB, ATRN, ITGAM, LTA4H, MPO
endoplasmic reticulum 3 ALB, CNR2, CYP2S1
extracellular space 6 ALB, ALOX5, ATRN, IGHE, ITGAM, MPO
perinuclear region of cytoplasm 2 ALOX5, PLCZ1
mitochondrion 2 CYP1A1, RAF1
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 6 CYP1A1, CYP1A2, CYP2S1, CYP3A4, MPO, OLR1
Microsome membrane 4 CYP1A1, CYP1A2, CYP2S1, CYP3A4
pronucleus 1 PLCZ1
Single-pass type I membrane protein 3 ATRN, IGHE, ITGAM
Secreted 3 ALB, MDK, OLR1
extracellular region 7 ALB, ALOX5, IGHE, LTA4H, MDK, MPO, OLR1
cytoplasmic side of plasma membrane 1 ALOX15
Mitochondrion outer membrane 1 CNR1
mitochondrial outer membrane 2 CNR1, RAF1
[Isoform 2]: Secreted 1 ATRN
anchoring junction 1 ALB
Nucleus membrane 1 ALOX5
nuclear membrane 1 ALOX5
external side of plasma membrane 1 ITGAM
actin cytoskeleton 1 CNR1
perikaryon 1 CNR2
cytoplasmic vesicle 1 C5AR1
nucleolus 1 PLCZ1
apical part of cell 1 C5AR1
Single-pass type II membrane protein 1 OLR1
postsynaptic membrane 1 CNR2
Cytoplasm, perinuclear region 2 ALOX5, PLCZ1
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 3 CNR1, ITGAM, OLR1
GABA-ergic synapse 1 CNR1
secretory granule 1 MPO
receptor complex 1 OLR1
ciliary basal body 1 ALB
chromatin 1 PPARA
IgE immunoglobulin complex 1 IGHE
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
[Isoform 2]: Cell membrane 1 IGHE
[Isoform 3]: Secreted 1 ATRN
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
Lipid droplet 1 ALOX15
Cell projection, dendrite 1 CNR2
specific granule membrane 2 ITGAM, OLR1
tertiary granule membrane 2 ITGAM, OLR1
pseudopodium 1 RAF1
azurophil granule 1 MPO
plasma membrane raft 1 ITGAM
ficolin-1-rich granule lumen 2 ALOX5, LTA4H
secretory granule lumen 1 ALOX5
secretory granule membrane 1 C5AR1
endoplasmic reticulum lumen 1 ALB
nuclear matrix 1 ALOX5
platelet alpha granule lumen 1 ALB
tertiary granule lumen 1 LTA4H
azurophil granule lumen 1 MPO
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
phagocytic vesicle lumen 1 MPO
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
[Isoform 1]: Cell membrane 1 ATRN
integrin complex 1 ITGAM
[Isoform 3]: Cell membrane 1 IGHE
[Isoform 1]: Secreted 1 IGHE
IgE B cell receptor complex 1 IGHE
immunoglobulin complex, circulating 1 IGHE
sperm head 1 PLCZ1
integrin alphaM-beta2 complex 1 ITGAM
Nucleus intermembrane space 1 ALOX5
ciliary transition fiber 1 ALB


文献列表

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