15-Keto-prostaglandin E2 (BioDeep_00000005626)

Main id: BioDeep_00000629501

 

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

化学式: C20H30O5 (350.2093)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCC(=O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)C(=O)C[C@H]1O
InChI: InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,19-/m1/s1

描述信息

15-keto-PGE2 is one of the prostaglandin E2 metabolites. (PMID 7190512). It is a degradation product produced by 15-hydroxy prostaglandin dehydrogenase (PGDH or 15-PGDH). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bones mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535). 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.
15-keto-PGE2 is one of the prostaglandin E2 metabolites. (PMID 7190512). It is a degradation product produced by 15-hydroxy prostaglandin dehydrogenase (PGDH or 15-PGDH)

同义名列表

27 个代谢物同义名

(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid; (5Z)-(13E)-11-alpha-Hydroxy-9,15-dioxoprosta-5,13-dienoic acid; (5Z,13E)-11-alpha-Hydroxy-9,15-dioxoprost-5,13-dienoic acid; (5Z)-(13E)-11-alpha-Hydroxy-9,15-dioxoprosta-5,13-dienoate; (5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoic acid; (5Z,13E)-11-alpha-Hydroxy-9,15-dioxoprost-5,13-dienoate; (5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoic acid; (5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoate; (5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoic acid; (5Z)-(15S)-11Α-hydroxy-9,15-dioxoprosta-13-enoic acid; (5Z,13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid; (5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoate; (5Z,13E)-11Α-hydroxy-9,15-dioxoprost-13-enoic acid; (5Z)-(15S)-11Α-hydroxy-9,15-dioxoprosta-13-enoate; (5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoate; 9,15-dioxo-11R-hydroxy-5Z,13E-prostadienoic acid; (5Z,13E)-11a-Hydroxy-9,15-dioxoprost-13-enoate; (5Z,13E)-11Α-hydroxy-9,15-dioxoprost-13-enoate; 9,15-Dioxo-11-hydroxyprosta-5,13-dienoic acid; 15-Ketoprostaglandin e2, (11alpha)-isomer; 15-Deoxy-15-oxo-prostaglandin e2; 15-keto-Prostaglandin E2; 15-Ketoprostaglandin e2; 15-Keto-pge2-alpha; 15-oxo-PGE2-alpha; 15-keto-PGE2; 15-oxo-PGE2



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(0)

BioCyc(0)

PlantCyc(0)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

9 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 10 CDK4, HPGD, KEAP1, NFE2, PGR, PPARG, PTGR2, PTGS2, SCYL1, STAT3
Peripheral membrane protein 3 AP1S2, GORASP1, PTGS2
Endoplasmic reticulum membrane 1 PTGS2
Nucleus 9 CDK4, GABPA, KEAP1, NFE2, PCNA, PGR, PPARG, SCYL1, STAT3
cytosol 9 AP1S2, CDK4, HPGD, KEAP1, PGR, PPARG, PPAT, SCYL1, STAT3
nuclear body 1 PCNA
centrosome 2 PCNA, SCYL1
nucleoplasm 9 CDK4, GABPA, HPGD, KEAP1, NFE2, PCNA, PGR, PPARG, STAT3
RNA polymerase II transcription regulator complex 3 NFE2, PPARG, STAT3
Cell membrane 1 PTGER4
Cytoplasmic side 2 AP1S2, GORASP1
Multi-pass membrane protein 1 PTGER4
Golgi apparatus membrane 1 GORASP1
Golgi apparatus 3 AP1S2, GORASP1, SCYL1
Golgi membrane 2 AP1S2, GORASP1
lysosomal membrane 1 AP1S2
plasma membrane 3 PGR, PTGER4, STAT3
Membrane 2 PTGER4, SCYL1
basolateral plasma membrane 1 HPGD
caveola 1 PTGS2
extracellular exosome 2 HPGD, PCNA
endoplasmic reticulum 2 KEAP1, PTGS2
perinuclear region of cytoplasm 1 PPARG
bicellular tight junction 1 CDK4
protein-containing complex 1 PTGS2
intracellular membrane-bounded organelle 2 AP1S2, PPARG
Microsome membrane 1 PTGS2
Secreted 1 SPAG11B
extracellular region 1 SPAG11B
mitochondrial outer membrane 1 PGR
transcription regulator complex 2 CDK4, STAT3
centriolar satellite 1 KEAP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 SCYL1
Nucleus membrane 1 CDK4
nuclear membrane 1 CDK4
nucleolus 1 CDK4
midbody 1 KEAP1
Early endosome 1 AP1S2
Membrane, clathrin-coated pit 1 AP1S2
clathrin-coated pit 1 AP1S2
cis-Golgi network 2 GORASP1, SCYL1
PML body 1 NFE2
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 1 PTGS2
chromatin 7 CDK4, GABPA, NFE2, PCNA, PGR, PPARG, STAT3
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
actin filament 1 KEAP1
Cul3-RING ubiquitin ligase complex 1 KEAP1
Endomembrane system 1 AP1S2
Cytoplasmic vesicle membrane 1 AP1S2
replication fork 1 PCNA
trans-Golgi network membrane 1 AP1S2
endoplasmic reticulum lumen 1 PTGS2
male germ cell nucleus 1 PCNA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
COPI vesicle coat 1 SCYL1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
nuclear lamina 1 PCNA
endoplasmic reticulum-Golgi intermediate compartment 1 SCYL1
protein-DNA complex 1 NFE2
AP-type membrane coat adaptor complex 1 AP1S2
membrane coat 1 AP1S2
Golgi apparatus, cis-Golgi network 1 SCYL1
AP-1 adaptor complex 1 AP1S2
cyclin-dependent protein kinase holoenzyme complex 2 CDK4, PCNA
inclusion body 1 KEAP1
[Isoform 4]: Mitochondrion outer membrane 1 PGR
cyclin D1-CDK4 complex 1 CDK4
cyclin D2-CDK4 complex 1 CDK4
cyclin D3-CDK4 complex 1 CDK4
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
[Isoform 6]: Nucleus 1 SCYL1


文献列表

  • Eun Ji Lee, Su-Jung Kim, Young-Il Hahn, Hyo-Jin Yoon, Bitnara Han, Kyeojin Kim, Seungbeom Lee, Kwang Pyo Kim, Young Ger Suh, Hye-Kyung Na, Young-Joon Surh. 15-Keto prostaglandin E2 suppresses STAT3 signaling and inhibits breast cancer cell growth and progression. Redox biology. 2019 05; 23(?):101175. doi: 10.1016/j.redox.2019.101175. [PMID: 31129031]
  • Robert J Evans, Katherine Pline, Catherine A Loynes, Sarah Needs, Maceler Aldrovandi, Jens Tiefenbach, Ewa Bielska, Rachel E Rubino, Christopher J Nicol, Robin C May, Henry M Krause, Valerie B O'Donnell, Stephen A Renshaw, Simon A Johnston. 15-keto-prostaglandin E2 activates host peroxisome proliferator-activated receptor gamma (PPAR-γ) to promote Cryptococcus neoformans growth during infection. PLoS pathogens. 2019 03; 15(3):e1007597. doi: 10.1371/journal.ppat.1007597. [PMID: 30921435]
  • Julio Mesa, Cristina Alsina, Udo Oppermann, Xavier Parés, Jaume Farrés, Sergio Porté. Human prostaglandin reductase 1 (PGR1): Substrate specificity, inhibitor analysis and site-directed mutagenesis. Chemico-biological interactions. 2015 Jun; 234(?):105-13. doi: 10.1016/j.cbi.2015.01.021. [PMID: 25619643]
  • Stacy Gelhaus Wendell, Franca Golin-Bisello, Sally Wenzel, Robert W Sobol, Fernando Holguin, Bruce A Freeman. 15-Hydroxyprostaglandin dehydrogenase generation of electrophilic lipid signaling mediators from hydroxy ω-3 fatty acids. The Journal of biological chemistry. 2015 Feb; 290(9):5868-80. doi: 10.1074/jbc.m114.635151. [PMID: 25586183]
  • Yu-Hsiang Yu, Yi-Cheng Chang, Tseng-Hsiung Su, Jiun-Yi Nong, Chao-Chin Li, Lee-Ming Chuang. Prostaglandin reductase-3 negatively modulates adipogenesis through regulation of PPARγ activity. Journal of lipid research. 2013 Sep; 54(9):2391-9. doi: 10.1194/jlr.m037556. [PMID: 23821743]
  • Dongdong Lu, Chang Han, Tong Wu. 15-hydroxyprostaglandin dehydrogenase-derived 15-keto-prostaglandin E2 inhibits cholangiocarcinoma cell growth through interaction with peroxisome proliferator-activated receptor-γ, SMAD2/3, and TAP63 proteins. The Journal of biological chemistry. 2013 Jul; 288(27):19484-502. doi: 10.1074/jbc.m113.453886. [PMID: 23687300]
  • Katsuko Shiraya, Taku Hirata, Ryo Hatano, Shushi Nagamori, Pattama Wiriyasermkul, Promsuk Jutabha, Mitsunobu Matsubara, Shigeaki Muto, Hidekazu Tanaka, Shinji Asano, Naohiko Anzai, Hitoshi Endou, Akira Yamada, Hiroyuki Sakurai, Yoshikatsu Kanai. A novel transporter of SLC22 family specifically transports prostaglandins and co-localizes with 15-hydroxyprostaglandin dehydrogenase in renal proximal tubules. The Journal of biological chemistry. 2010 Jul; 285(29):22141-51. doi: 10.1074/jbc.m109.084426. [PMID: 20448048]
  • Gregory S Harmon, Darren S Dumlao, Damian T Ng, Kim E Barrett, Edward A Dennis, Hui Dong, Christopher K Glass. Pharmacological correction of a defect in PPAR-gamma signaling ameliorates disease severity in Cftr-deficient mice. Nature medicine. 2010 Mar; 16(3):313-8. doi: 10.1038/nm.2101. [PMID: 20154695]
  • Jinsheng Yang, Charles E Petersen, Chung-Eun Ha, Nadhipuram V Bhagavan. Structural insights into human serum albumin-mediated prostaglandin catalysis. Protein science : a publication of the Protein Society. 2002 Mar; 11(3):538-45. doi: 10.1110/ps.28702. [PMID: 11847277]
  • S Sakuma, Y Fujimoto, Y Miyata, K Yamane, H Nishida, T Fujita. Inhibition of 15-hydroxy prostaglandin dehydrogenase activity in rabbit gastric antral mucosa by 13-hydroperoxyoctadecadienoic acid. Prostaglandins, leukotrienes, and essential fatty acids. 1994 Dec; 51(6):425-30. doi: 10.1016/0952-3278(94)90060-4. [PMID: 7708809]
  • S Sakuma, Y Fujimoto, M Okumura, H Nishida, I Yamamoto, T Fujita. The effects of arachidonic acid and its CoA ester on the catabolism of prostaglandin E2 in rabbit kidney cortex. Biochemistry international. 1992 Jul; 27(2):291-9. doi: . [PMID: 1323964]
  • E D Watson, C R Stokes, F J Bourne. Effect of exogenous ovarian steroids on the uterine luminal prostaglandins in ovariectomised mares with experimental endometritis. Research in veterinary science. 1988 May; 44(3):361-5. doi: 10.1016/s0034-5288(18)30872-5. [PMID: 3165540]
  • A R Morrison, J R Crowley. Identification of an unusual cyclooxygenase metabolite of arachidonic acid in rabbit renal medulla. Archives of biochemistry and biophysics. 1984 Nov; 234(2):413-7. doi: 10.1016/0003-9861(84)90287-x. [PMID: 6437329]
  • D G Chang, H H Tai. Characterization of two enzyme proteins catalyzing NADP+/NADPH-dependent oxidoreduction of prostaglandins at C-9 and C-15 from swine kidney. Archives of biochemistry and biophysics. 1982 Apr; 214(2):464-74. doi: 10.1016/0003-9861(82)90050-9. [PMID: 6807198]