Prostaglandin J2 (BioDeep_00000003318)

 

Secondary id: BioDeep_00000174979, BioDeep_00000404647, BioDeep_00000629495

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid

化学式: C20H30O4 (334.2144)
中文名称: 前列腺素J2
谱图信息: 最多检出来源 Homo sapiens(blood) 28.14%

分子结构信息

SMILES: CCCCCC(C=CC1C(C=CC1=O)CC=CCCCC(=O)O)O
InChI: InChI=1S/C20H30O4/c1-2-3-6-10-17(21)13-14-18-16(12-15-19(18)22)9-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-13+/t16-,17-,18+/m0/s1

描述信息

Prostaglandin J2 (PGJ2) is an endogenous product of inflammation in humans. It induces neuronal death and the accumulation of ubiquitinated proteins into distinct aggregates. It may play a role in neurodegenerative disorders inducing a chain of events that culminates in neuronal cell death. An altered expression of enzymes in PGJ2 synthesis may represent a novel pathogenic mechanism in human obesity. The peroxisome proliferator-activated receptor gamma (PPARγ) has a fundamental role in glucose homeostasis and adipocyte differentiation. Besides linoleate, linolenate and arachidonate, the most notable PPAR ligand is 15-deoxy-delta12-14-prostaglandin J2, a natural derivative of prostaglandin D2 and PGJ2. It is therefore plausible that the production of 15d-PGJ2 within adipose tissue may act as an endogenous mediator of adipocyte differentiation. PGJ2 disrupts the cytoskeleton in neuronal cells. This cyclopentenone prostaglandin triggered endoplasmic reticulum (ER) collapse and the redistribution of ER proteins, such as calnexin and catechol-O-methyltransferase, into a large centrosomal aggregate containing ubiquitinated proteins and alpha-synuclein. The PGJ2-dependent cytoskeletal rearrangement paralleled the development of the large centrosomal aggregate. Supporting a mechanism by which, upon PGJ2 treatment, cytoskeleton/ER collapse coincides with the relocation of ER proteins, other potentially neighboring proteins, and ubiquitinated proteins into centrosomal aggregates. Development of these large perinuclear aggregates is associated with disruption of the microtubule/ER network. This aberrant protein deposition, triggered by a product of inflammation, may be common to other compounds that disrupt microtubules and induce protein aggregation, such as MPP+ and rotenone, found to be associated with neurodegeneration. Many neurodegenerative disorders, such as Parkinson disease, exhibit inclusion bodies containing ubiquitinated proteins. Concentrations of PGJ2 in biofluids have not been established, since this prostaglandin is further metabolized into delta12-PGJ2, and 15-deoxy-delta12,14-PGJ2. (PMID: 16737963, 16842938, 16774923)Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
Prostaglandin J2 (PGJ2) is an endogenous product of inflammation in humans. It induces neuronal death and the accumulation of ubiquitinated proteins into distinct aggregates. It may play a role in neurodegenerative disorders inducing a chain of events that culminates in neuronal cell death. An altered expression of enzymes in PGJ2 synthesis may represent a novel pathogenic mechanism in human obesity. The peroxisome proliferator-activated receptor gamma (PPARγ) has a fundamental role in glucose homeostasis and adipocyte differentiation. Besides linoleate, linolenate and arachidonate, the most notable PPAR ligand is 15-deoxy-delta12-14-prostaglandin J2, a natural derivative of prostaglandin D2 and PGJ2. It is therefore plausible that the production of 15d-PGJ2 within adipose tissue may act as an endogenous mediator of adipocyte differentiation. PGJ2 disrupts the cytoskeleton in neuronal cells. This cyclopentenone prostaglandin triggered endoplasmic reticulum (ER) collapse and the redistribution of ER proteins, such as calnexin and catechol-O-methyltransferase, into a large centrosomal aggregate containing ubiquitinated proteins and alpha-synuclein. The PGJ2-dependent cytoskeletal rearrangement paralleled the development of the large centrosomal aggregate. Supporting a mechanism by which, upon PGJ2 treatment, cytoskeleton/ER collapse coincides with the relocation of ER proteins, other potentially neighboring proteins, and ubiquitinated proteins into centrosomal aggregates. Development of these large perinuclear aggregates is associated with disruption of the microtubule/ER network. This aberrant protein deposition, triggered by a product of inflammation, may be common to other compounds that disrupt microtubules and induce protein aggregation, such as MPP+ and rotenone, found to be associated with neurodegeneration. Many neurodegenerative disorders, such as Parkinson disease, exhibit inclusion bodies containing ubiquitinated proteins. Concentrations of PGJ2 in biofluids have not been established, since this prostaglandin is further metabolized into delta12-PGJ2, and 15-deoxy-delta12,14-PGJ2. (PMID: 16737963, 16842938, 16774923)
D000970 - Antineoplastic Agents

同义名列表

11 个代谢物同义名

(5Z)-7-[(1S,5R)-5-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid; 11-oxo-15S-Hydroxy-5Z,8Z,13E-prostatrienoic acid; 11-oxo-15S-Hydroxy-5Z,8Z,13E-prostatrienoate; 9-Deoxy-delta-9-prostaglandin D2; 9-Deoxy-δ-9-prostaglandin D2; 9-Deoxy-delta-9-PGD2; 9-Deoxy-δ-9-PGD2; MCULE-3363997729; Prostaglandin J2; PGJ2; Prostaglandin J2



数据库引用编号

27 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

55 个相关的代谢反应过程信息。

Reactome(5)

BioCyc(0)

WikiPathways(4)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

PharmGKB(0)

10 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 11 ADIG, AKT1, CASP3, HPGD, MAPK14, MAPK8, NFE2L2, NFKB1, PPARG, PTGS2, STAT3
Peripheral membrane protein 2 AP1S2, PTGS2
Endoplasmic reticulum membrane 3 HMOX1, PTGDS, PTGS2
Nucleus 12 ADIG, AKT1, CASP3, HMOX1, JUN, MAPK14, MAPK8, NFE2L2, NFKB1, PPARA, PPARG, STAT3
cytosol 11 AKT1, AP1S2, CASP3, HMOX1, HPGD, MAPK14, MAPK8, NFE2L2, NFKB1, PPARG, STAT3
centrosome 1 NFE2L2
nucleoplasm 12 AKT1, CASP3, HMOX1, HPGD, JUN, MAPK14, MAPK8, NFE2L2, NFKB1, PPARA, PPARG, STAT3
RNA polymerase II transcription regulator complex 4 JUN, NFE2L2, PPARG, STAT3
Cell membrane 3 AKT1, PTGDR2, TNF
Cytoplasmic side 2 AP1S2, HMOX1
lamellipodium 1 AKT1
Multi-pass membrane protein 1 PTGDR2
Synapse 1 MAPK8
cell cortex 1 AKT1
cell surface 1 TNF
glutamatergic synapse 3 AKT1, CASP3, MAPK14
Golgi apparatus 3 AP1S2, NFE2L2, PTGDS
Golgi membrane 1 AP1S2
lysosomal membrane 1 AP1S2
neuronal cell body 2 CASP3, TNF
postsynapse 1 AKT1
Cytoplasm, cytosol 1 NFE2L2
plasma membrane 5 AKT1, NFE2L2, PTGDR2, STAT3, TNF
Membrane 3 ADIG, AKT1, HMOX1
axon 1 MAPK8
basolateral plasma membrane 1 HPGD
caveola 1 PTGS2
extracellular exosome 2 HPGD, PTGDS
endoplasmic reticulum 2 HMOX1, PTGS2
extracellular space 5 CXCL8, HMOX1, IL6, PTGDS, TNF
perinuclear region of cytoplasm 3 HMOX1, PPARG, PTGDS
mitochondrion 2 MAPK14, NFKB1
protein-containing complex 2 AKT1, PTGS2
intracellular membrane-bounded organelle 2 AP1S2, PPARG
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Secreted 4 ADIG, CXCL8, IL6, PTGDS
extracellular region 7 ADIG, CXCL8, IL6, MAPK14, NFKB1, PTGDS, TNF
Single-pass membrane protein 1 ADIG
mitochondrial outer membrane 1 HMOX1
transcription regulator complex 3 JUN, NFKB1, STAT3
Nucleus membrane 1 PTGDS
nuclear membrane 1 PTGDS
external side of plasma membrane 1 TNF
microtubule cytoskeleton 1 AKT1
Early endosome 1 AP1S2
Membrane, clathrin-coated pit 1 AP1S2
cell-cell junction 1 AKT1
clathrin-coated pit 1 AP1S2
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Cytoplasm, perinuclear region 1 PTGDS
Membrane raft 1 TNF
spindle 1 AKT1
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 PPARG
neuron projection 2 PTGDR2, PTGS2
ciliary basal body 1 AKT1
chromatin 6 JUN, NFE2L2, NFKB1, PPARA, PPARG, STAT3
mediator complex 1 NFE2L2
phagocytic cup 1 TNF
spindle pole 1 MAPK14
nuclear chromosome 1 JUN
Endomembrane system 1 AP1S2
Lipid droplet 1 ADIG
Cytoplasmic vesicle membrane 1 AP1S2
euchromatin 1 JUN
trans-Golgi network membrane 1 AP1S2
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 MAPK14, NFKB1
endoplasmic reticulum lumen 2 IL6, PTGS2
specific granule lumen 1 NFKB1
Single-pass type IV membrane protein 1 HMOX1
protein-DNA complex 1 NFE2L2
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
AP-type membrane coat adaptor complex 1 AP1S2
membrane coat 1 AP1S2
Rough endoplasmic reticulum 1 PTGDS
AP-1 adaptor complex 1 AP1S2
transcription factor AP-1 complex 1 JUN
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Carl Eguez, Michelle A Clark, Ann Tenneil O'Connor. 15-Deoxy-Δ-12,14-prostaglandin J2 effects in vascular smooth muscle cells: Implications in vascular smooth muscle cell proliferation and contractility. Prostaglandins & other lipid mediators. 2021 10; 156(?):106583. doi: 10.1016/j.prostaglandins.2021.106583. [PMID: 34332056]
  • Christoph Schmöcker, Heike Gottschall, Katharina M Rund, Laura Kutzner, Fabian Nolte, Annika I Ostermann, Dirk Hartmann, Nils Helge Schebb, Karsten H Weylandt. Oxylipin patterns in human colon adenomas. Prostaglandins, leukotrienes, and essential fatty acids. 2021 04; 167(?):102269. doi: 10.1016/j.plefa.2021.102269. [PMID: 33812217]
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