Prostaglandin E1 (BioDeep_00000001682)

 

Secondary id: BioDeep_00001867819

natural product human metabolite Endogenous blood metabolite Chemicals and Drugs PANOMIX_OTCML-2023 Cytotoxicity


代谢物信息卡片


7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

化学式: C20H34O5 (354.2406)
中文名称: 前列腺素 E1
谱图信息: 最多检出来源 Homo sapiens(plant) 6.97%

Reviewed

Last reviewed on 2024-07-09.

Cite this Page

Prostaglandin E1. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/prostaglandin_e1 (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001682). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCC(C=CC1C(CC(=O)C1CCCCCCC(=O)O)O)O
InChI: InChI=1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1

描述信息

Prostaglandin E1 (PGE1) is a potent endogenous vasodilator agent that increases peripheral blood flow. It inhibits platelet aggregation and has many other biological effects such as bronchodilation, mediation of inflammation, and various protective functions. The protective action of PGE1 has been shown on both experimental animal models of liver injury and patients with fulminant viral hepatitis. PGE1-treated cirrhotic rats had less hepatosplenomegaly, lower serum alanine aminotransferase levels and portal pressures, and higher arterial pressure than placebo-treated cirrhotic rats. There are several mechanisms of PGE1 hepatic cytoprotection: inhibiting T-cell mediated cytotoxicity, enhancing DNA synthesis of the injured liver after partial hepatectomy by stimulating cyclic AMP production, increasing ATP level in hepatic tissue to accelerate the recovery of mitochondrial respiratory function after reperfusion, and stabilizing membrane microviscosity. PGE1 is a prostanoid. The term prostanoid collectively describes prostaglandins, prostacyclins, and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They are derived from C-20 polyunsaturated fatty acids, mainly dihomo-γ-linolenic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2) (PMID: 11819590, 16986207). 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 and are 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 E1 (Alprostadil) is a prostanoid receptor ligand, with Kis of 1.1 nM, 2.1 nM, 10 nM, 33 nM and 36 nM for mouse EP3, EP4, EP2, IP and EP1, respectively. Prostaglandin E1 induces vasodilation and inhibits platelet aggregation. Prostaglandin E1 can be used as a vasodilator for the research of peripheral vascular diseases[1][2][3].

同义名列表

78 个代谢物同义名

7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid; (-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid; (+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid; (-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate; (+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate; 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid; 3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate; (11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid; 11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (acd/name 4.0); (13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoic acid; (13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid; (11Α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oic acid; (11a,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid; (11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate; 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid; (13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoate; (13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acid; (11a,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate; (13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate; (13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid; (11Α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oate; (13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid; 11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoate; (13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoate; (13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate; (13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoate; 11Α,15α-dihydroxy-9-oxo-13-trans-prostenoic acid; 11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acid; 11a,15a-Dihydroxy-9-oxo-13-trans-prostenoate; 11Α,15α-dihydroxy-9-oxo-13-trans-prostenoate; 9-oxo-11R,15S-dihydroxy-13E-prostaenoic acid; 11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid; 11,15-Dihydroxy-9-oxoprost-13-en-1-Oate; Schwarz pharma brand OF alprostadil; Pharmacia brand 1 OF alprostadil; Pharmacia brand 2 OF alprostadil; AstraZeneca brand OF alprostadil; Schwarz brand OF alprostadil; Allphar brand OF alprostadil; Janssen brand OF alprostadil; Paladin brand OF alprostadil; Alprostadil prostoglandin e1; Abbott brand OF alprostadil; Vivus brand OF alprostadil; Hoyer brand OF alprostadil; Astra brand OF alprostadil; Prostaglandin e1alpha; (-)-Prostaglandin e1; Prostin VR pediatric; L-Prostaglandin e1; U-10136alprostadil; Alprostadil(usan); Caverject impulse; Prostaglandin E1; U-10136prostin; Ovinonic acid; Alprostadilum; Vasaprostan; Prostine VR; Alprostadil; Prostavasin; FA 20:3;O3; Prostin VR; lipo PGE1; lipo-PGE1; PGE1alpha; Caverject; Sugiran; Vitaros; Viridal; Minprog; Prink; PGE-1; Befar; PGE1; Muse; Edex; Alprostadil



数据库引用编号

29 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

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)

31 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 6 ALB, ANG, PRL, PTGS2, VASP, VEGFA
Peripheral membrane protein 2 AP1S2, PTGS2
Endoplasmic reticulum membrane 1 PTGS2
Nucleus 4 ALB, ANG, PRL, VEGFA
cytosol 4 ALB, ANG, AP1S2, VASP
centrosome 1 ALB
nucleoplasm 1 PRL
RNA polymerase II transcription regulator complex 1 PRL
Cell membrane 7 ADRB3, ITGAM, PTGER1, PTGER2, PTGER3, PTGER4, SELP
Cytoplasmic side 1 AP1S2
lamellipodium 1 VASP
Multi-pass membrane protein 6 ADRB3, CACNA1I, PTGER1, PTGER2, PTGER3, PTGER4
cell surface 2 ITGAM, VEGFA
glutamatergic synapse 1 VASP
Golgi apparatus 3 ALB, AP1S2, VEGFA
Golgi membrane 1 AP1S2
growth cone 1 ANG
lysosomal membrane 1 AP1S2
neuronal cell body 1 ANG
postsynapse 1 VASP
plasma membrane 12 ADRB3, CACNA1I, F2, GCG, IFNLR1, ITGAM, PTGER1, PTGER2, PTGER3, PTGER4, SELP, VASP
Membrane 7 CACNA1I, IFNLR1, ITGAM, PTGER2, PTGER3, PTGER4, VEGFA
caveola 1 PTGS2
extracellular exosome 6 ALB, F2, ITGAM, SELP, VASP, VWF
endoplasmic reticulum 4 ALB, PTGS2, VEGFA, VWF
extracellular space 10 ALB, ANG, F2, GCG, IL10, ITGAM, PRL, SELP, VEGFA, VWF
Cell junction, tight junction 1 VASP
adherens junction 1 VEGFA
bicellular tight junction 1 VASP
protein-containing complex 2 ALB, PTGS2
intracellular membrane-bounded organelle 1 AP1S2
Microsome membrane 1 PTGS2
filopodium 1 VASP
Single-pass type I membrane protein 3 IFNLR1, ITGAM, SELP
Secreted 9 ALB, ANG, F2, GCG, IL10, PRL, SELP, VEGFA, VWF
extracellular region 9 ALB, ANG, F2, GCG, IL10, PRL, SELP, VEGFA, VWF
anchoring junction 1 ALB
external side of plasma membrane 2 ITGAM, SELP
Secreted, extracellular space, extracellular matrix 2 VEGFA, VWF
actin cytoskeleton 2 ANG, VASP
nucleolus 1 ANG
Early endosome 1 AP1S2
Membrane, clathrin-coated pit 1 AP1S2
clathrin-coated pit 1 AP1S2
Cell projection, lamellipodium 1 VASP
Membrane raft 1 ITGAM
Cytoplasm, cytoskeleton 1 VASP
focal adhesion 1 VASP
extracellular matrix 2 VEGFA, VWF
basement membrane 1 ANG
collagen-containing extracellular matrix 2 F2, VWF
secretory granule 1 VEGFA
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 ADRB3
neuron projection 1 PTGS2
ciliary basal body 1 ALB
chromatin 1 PRL
cell projection 1 VASP
Chromosome 1 ANG
cytoskeleton 1 VASP
centriole 1 ALB
Nucleus, nucleolus 1 ANG
spindle pole 1 ALB
blood microparticle 2 ALB, F2
nuclear envelope 1 PTGER3
Endomembrane system 1 AP1S2
endosome lumen 1 PRL
Cytoplasmic vesicle membrane 1 AP1S2
specific granule membrane 1 ITGAM
tertiary granule membrane 1 ITGAM
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
filopodium membrane 1 VASP
platelet alpha granule 1 VWF
trans-Golgi network membrane 1 AP1S2
platelet dense granule membrane 1 SELP
plasma membrane raft 1 ITGAM
secretory granule lumen 1 GCG
Golgi lumen 1 F2
endoplasmic reticulum lumen 4 ALB, F2, GCG, PTGS2
platelet alpha granule lumen 3 ALB, VEGFA, VWF
voltage-gated calcium channel complex 1 CACNA1I
endocytic vesicle 1 ANG
AP-type membrane coat adaptor complex 1 AP1S2
membrane coat 1 AP1S2
AP-1 adaptor complex 1 AP1S2
platelet alpha granule membrane 1 SELP
integrin complex 1 ITGAM
lamellipodium membrane 1 VASP
[Glucagon-like peptide 1]: Secreted 1 GCG
platelet dense granule lumen 1 SELP
angiogenin-PRI complex 1 ANG
Weibel-Palade body 1 VWF
integrin alphaM-beta2 complex 1 ITGAM
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
ciliary transition fiber 1 ALB
interleukin-28 receptor complex 1 IFNLR1


文献列表

  • Sebile Azırak. Prevention of nephrotoxicity induced by amikacin: The role of misoprostol, A prostaglandin E1 analogue. Prostaglandins & other lipid mediators. 2023 Feb; 164(?):106682. doi: 10.1016/j.prostaglandins.2022.106682. [PMID: 36349661]
  • Decai Zhu, Dawei Wang, Zhen Zhao, Qingqing Liu, Rongyuan Yang, Qing Liu. Application of Nanoliposome Alprostadil in the Perioperative Period of Percutaneous Coronary Intervention to Reduce In-Stent Restenosis: A Systematic Review and Meta-Analysis. Journal of interventional cardiology. 2023; 2023(?):4100197. doi: 10.1155/2023/4100197. [PMID: 37251365]
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  • Nina Buchtele, Christian Schörgenhofer, Michael Schwameis, Bernd Jilma, Peter Schellongowski, Harald Herkner, Katharina Riss, Monika Schmid, Alexander Hermann, Oliver Robak, Bernhard Nagler, Ludwig Traby, Andja Bojic, Thomas Staudinger. Add-On Prostaglandin E1 in Venovenous Extracorporeal Membrane Oxygenation: A Randomized, Double-Blind, Placebo-controlled Pilot Trial. American journal of respiratory and critical care medicine. 2022 07; 206(2):170-177. doi: 10.1164/rccm.202110-2359oc. [PMID: 35426776]
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  • Xiaogang Liu, Peng Zhang, Jing Zhang, Xue Zhang, Shicheng Yang, Naikuan Fu. The Preventive Effect of Alprostadil on the Contrast-Induced Nephropathy of Coronary Heart Disease Treated by Percutaneous Coronary Intervention in Moderate and High-Risk Population Stratified by Mehran Score. Angiology. 2022 Jan; 73(1):33-41. doi: 10.1177/00033197211015540. [PMID: 34098771]
  • Tiphaine Belleville-Rolland, Alexandre Leuci, Alexandre Mansour, Benoit Decouture, Fanny Martin, Sonia Poirault-Chassac, Margot Rouaud, Hippolyte Guerineau, Blandine Dizier, Dominique Pidard, Pascale Gaussem, Christilla Bachelot-Loza. Role of Membrane Lipid Rafts in MRP4 (ABCC4) Dependent Regulation of the cAMP Pathway in Blood Platelets. Thrombosis and haemostasis. 2021 12; 121(12):1628-1636. doi: 10.1055/a-1481-2663. [PMID: 33851387]
  • Sunny Z Hussain, Barrett Labrum, Shadreck Mareya, Stephen Stripling, Robert Clifford. Safety of Lubiprostone in Pediatric Patients With Functional Constipation: A Nonrandomized, Open-Label Trial. Journal of pediatric gastroenterology and nutrition. 2021 11; 73(5):572-578. doi: 10.1097/mpg.0000000000003280. [PMID: 34387619]
  • Hongling Xu, Hongye Wang, Chuang Zhang, Jun Xiao, Ning Hua, Xuezheng Tang, Jiaqi Xie, Zhengbin Zhang. Efficacy of Alprostadil in Preventing Contrast-Induced Nephropathy: A Systematic Review and Meta-Analysis. Angiology. 2021 10; 72(9):878-888. doi: 10.1177/00033197211004412. [PMID: 33853365]
  • Heeju Lee, Bora Lee, Yeonhee Kim, Sohyun Min, Eunjoo Yang, Seungmin Lee. Effects of Sodium Selenite Injection on Serum Metabolic Profiles in Women Diagnosed with Breast Cancer-Related Lymphedema-Secondary Analysis of a Randomized Placebo-Controlled Trial Using Global Metabolomics. Nutrients. 2021 Sep; 13(9):. doi: 10.3390/nu13093253. [PMID: 34579131]
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  • Yosuke Ida, Megumi Watanabe, Araya Umetsu, Hiroshi Ohguro, Fumihito Hikage. Addition of EP2 agonists to an FP agonist additively and synergistically modulates adipogenesis and the physical properties of 3D 3T3-L1 sphenoids. Prostaglandins, leukotrienes, and essential fatty acids. 2021 08; 171(?):102315. doi: 10.1016/j.plefa.2021.102315. [PMID: 34246925]
  • Francisco H Velásquez-Forero, Pedro F Valencia-Mayoral. Histomorphometry evaluation of bone anabolism promoted by prostaglandin E1 and its relation to hypercalcemia. Boletin medico del Hospital Infantil de Mexico. 2021 06; 78(4):293-300. doi: 10.24875/bmhim.20000080. [PMID: 34077409]
  • Jenny T Mao, Bingye Xue, Sili Fan, Patricia Neis, Clifford Qualls, Larry Massie, Oliver Fiehn. Leucoselect Phytosome Modulates Serum Eicosapentaenoic Acid, Docosahexaenoic Acid, and Prostaglandin E3 in a Phase I Lung Cancer Chemoprevention Study. Cancer prevention research (Philadelphia, Pa.). 2021 06; 14(6):619-626. doi: 10.1158/1940-6207.capr-20-0585. [PMID: 33707173]
  • Jing Cui, Kai Shan, Qin Yang, Yumin Qi, Hongyan Qu, Jiaqi Li, Rong Wang, Lingling Jia, Wei Chen, Ninghan Feng, Yong Q Chen. Prostaglandin E3 attenuates macrophage-associated inflammation and prostate tumour growth by modulating polarization. Journal of cellular and molecular medicine. 2021 06; 25(12):5586-5601. doi: 10.1111/jcmm.16570. [PMID: 33982835]
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