19-Hydroxy-PGE2 (BioDeep_00000020831)
human metabolite Endogenous
代谢物信息卡片
化学式: C20H32O6 (368.2198772)
中文名称:
谱图信息:
最多检出来源 Bos taurus(endogenous) 50%
分子结构信息
SMILES: CC(CCCC(C=CC1C(CC(=O)C1CC=CCCCC(=O)O)O)O)O
InChI: InChI=1S/C20H32O6/c1-14(21)7-6-8-15(22)11-12-17-16(18(23)13-19(17)24)9-4-2-3-5-10-20(25)26/h2,4,11-12,14-17,19,21-22,24H,3,5-10,13H2,1H3,(H,25,26)/b4-2-,12-11+/t14-,15+,16-,17-,19-/m1/s1
描述信息
19-Hydroxy-PGE2 is a derivative of PGE2. Both 19-Hydroxy-PGE1 and 19-hydroxy-PGE2 are formed from PGE1 and PGE2 by prostaglandin 19-hydroxylase, a cytochrome P-450 enzyme, in seminal vesicles (PMID: 3196735). 19-Hydroxy-PGE2 is a selective prostanoid EP2-receptor agonist; it doesnt stimulate FP-receptors, and is devoid of activity on thromboxane A2, prostaglandin D2 and prostacyclin sensitive receptors. 19-OH PGE2 is formed in large quantities from PGE2 in human seminal plasma. PGE2 is 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). (PMID: 16978535, 8248550, 817207). 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.
19-Hydroxy-PGE2 is a derivative of PGE2. Both 19-Hydroxy-PGE1 and 19-hydroxy-PGE2 are formed from PGE1 and PGE2 by prostaglandin 19-hydroxylase, a cytochrome P-450 enzyme, in seminal vesicles (PMID: 3196735). 19-Hydroxy-PGE2 is a selective prostanoid EP2-receptor agonist; it doesnt stimulate FP-receptors, and is devoid of activity on thromboxane A2, prostaglandin D2 and prostacyclin sensitive receptors. 19-OH PGE2 is formed in large quantities from PGE2 in human seminal plasma. PGE2 is 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). (PMID: 16978535, 8248550, 817207)
同义名列表
10 个代谢物同义名
(5Z)-7-[(1R,2R,3R)-2-[(1E,3S,7R)-3,7-dihydroxyoct-1-en-1-yl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic acid; 9-oxo-11R,15S,19R-trihydroxy-5Z,13E-prostadienoic acid; 9-oxo-11R,15S,19R-Trihydroxy-5Z,13E-prostadienoate; 15(R),19(R)-hydroxy Prostaglandin E2; 19(R)-hydroxy-Prostaglandin E2; 19-Hydroxyprostaglandin e2; 19R-19-Hydroxy pge-2; 19(R)-Hydroxy-pge2; 19-hydroxy-PGE2; Eganoprost
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:165313
- PubChem: 5283038
- PubChem: 1453
- HMDB: HMDB0001908
- foodb: FDB022733
- chemspider: 4446165
- CAS: 64625-54-3
- CAS: 55123-68-7
- PMhub: MS000051133
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 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
- F C Denison, V E Grant, A A Calder, R W Kelly. Seminal plasma components stimulate interleukin-8 and interleukin-10 release.
Molecular human reproduction.
1999 Mar; 5(3):220-6. doi:
10.1093/molehr/5.3.220
. [PMID: 10333355] - Y Boie, R Stocco, N Sawyer, D M Slipetz, M D Ungrin, F Neuschäfer-Rube, G P Püschel, K M Metters, M Abramovitz. Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.
European journal of pharmacology.
1997 Dec; 340(2-3):227-41. doi:
10.1016/s0014-2999(97)01383-6
. [PMID: 9537820] - D F Woodward, C E Protzman, A H Krauss, L S Williams. Identification of 19 (R)-OH prostaglandin E2 as a selective prostanoid EP2-receptor agonist.
Prostaglandins.
1993 Oct; 46(4):371-83. doi:
10.1016/0090-6980(93)90102-d
. [PMID: 8248550] - G Skibinski, R W Kelly, C M Harrison, L A McMillan, K James. Relative immunosuppressive activity of human seminal prostaglandins.
Journal of reproductive immunology.
1992 Aug; 22(2):185-95. doi:
10.1016/0165-0378(92)90015-v
. [PMID: 1501205] - A J Quayle, R W Kelly, T B Hargreave, K James. Immunosuppression by seminal prostaglandins.
Clinical and experimental immunology.
1989 Mar; 75(3):387-91. doi:
NULL
. [PMID: 2702780] - R Freixia, J Rosello, I Ramis, J Abian, O Bulbena, M Brassesco, E Gelpi. Prostaglandin levels in infertile patients affected by asthenozoospermia and prostatitis.
Prostaglandins, leukotrienes, and essential fatty acids.
1988 Jan; 31(1):41-4. doi:
10.1016/0952-3278(88)90163-9
. [PMID: 3375285]