Prostaglandin B2 (BioDeep_00000004024)

 

Secondary id: BioDeep_00000405082

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


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

化学式: C20H30O4 (334.2144)
中文名称: 前列腺素 B2
谱图信息: 最多检出来源 Homo sapiens(blood) 24.41%

Reviewed

Last reviewed on 2024-08-14.

Cite this Page

Prostaglandin B2. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/prostaglandin_b2 (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000004024). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCCCCC(C=CC1=C(C(=O)CC1)CC=CCCCC(=O)O)O
InChI: InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-/m0/s1

描述信息

Prostaglandin B2 (PGB2) is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (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). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 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, 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 B2 (PGB2) is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (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). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207)

同义名列表

7 个代谢物同义名

(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid; (5Z,13E,15R)-15-hydroxy-9-oxoprosta-5,8(12),13-trien-1-oic acid; Prostaglandin B2; PGB2; 7-[2-(3-hydroxyoct-1-enyl)-5-oxocyclopenten-1-yl]hept-5-enoic acid; 15S-hydroxy-9-oxo-5Z,8(12),13E-prostatrienoic acid; Prostaglandin B2



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

52 个相关的代谢反应过程信息。

Reactome(5)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

PharmGKB(0)

23 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 7 ALB, ARG1, CNR2, ITPR3, MYLK, PTGS2, TUBB4B
Peripheral membrane protein 3 AP1S2, CYP1B1, PTGS2
Endoplasmic reticulum membrane 4 CD4, CYP1B1, ITPR3, PTGS2
Nucleus 4 ALB, ARG1, CIART, TUBB4B
cytosol 6 ALB, AP1S2, ARG1, MYLK, NGF, TUBB4B
dendrite 2 CNR2, NGF
centrosome 1 ALB
nucleoplasm 1 ITPR3
Cell membrane 3 CD4, CYSLTR2, TNF
Cytoplasmic side 1 AP1S2
Cleavage furrow 1 MYLK
lamellipodium 1 MYLK
Cytoplasmic granule 1 ARG1
Multi-pass membrane protein 2 CYSLTR2, ITPR3
Synapse 1 MYLK
cell surface 2 TNF, TPO
Golgi apparatus 2 ALB, AP1S2
Golgi membrane 2 AP1S2, INS
lysosomal membrane 1 AP1S2
neuronal cell body 2 ITPR3, TNF
synaptic vesicle 1 NGF
plasma membrane 8 CD4, CNR2, CYSLTR2, GCG, ITPR3, MYLK, TNF, TPO
Membrane 3 CYP1B1, ITPR3, TPO
axon 1 NGF
brush border 1 ITPR3
caveola 1 PTGS2
extracellular exosome 3 ALB, SPINK1, TUBB4B
endoplasmic reticulum 4 ALB, CNR2, ITPR3, PTGS2
extracellular space 9 ALB, ARG1, GCG, IL6, INS, NGF, TG, TNF, TPO
mitochondrion 1 CYP1B1
protein-containing complex 2 ALB, PTGS2
intracellular membrane-bounded organelle 2 AP1S2, CYP1B1
Microsome membrane 2 CYP1B1, PTGS2
Single-pass type I membrane protein 2 CD4, TPO
Secreted 7 ALB, GCG, IL6, INS, NGF, SPINK1, TG
extracellular region 9 ALB, ARG1, GCG, IL6, INS, NGF, TG, TNF, TUBB4B
anchoring junction 1 ALB
external side of plasma membrane 2 CD4, TNF
Extracellular vesicle 1 TUBB4B
actin cytoskeleton 1 MYLK
perikaryon 1 CNR2
microtubule cytoskeleton 1 TUBB4B
nucleolus 1 ITPR3
Early endosome 2 AP1S2, CD4
Membrane, clathrin-coated pit 1 AP1S2
apical part of cell 1 ITPR3
clathrin-coated pit 1 AP1S2
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 CNR2
Cell projection, lamellipodium 1 MYLK
Membrane raft 2 CD4, TNF
Cytoplasm, cytoskeleton 1 TUBB4B
microtubule 1 TUBB4B
sarcoplasmic reticulum 1 ITPR3
Nucleus, PML body 1 CIART
PML body 1 CIART
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 2 ITPR3, PTGS2
receptor complex 1 ITPR3
neuron projection 1 PTGS2
ciliary basal body 1 ALB
phagocytic cup 1 TNF
mitotic spindle 1 TUBB4B
cytoskeleton 1 TUBB4B
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
Endomembrane system 1 AP1S2
endosome lumen 2 INS, NGF
axonemal microtubule 1 TUBB4B
Cytoplasmic vesicle membrane 1 AP1S2
Cell projection, dendrite 1 CNR2
stress fiber 1 MYLK
trans-Golgi network membrane 1 AP1S2
secretory granule lumen 2 GCG, INS
secretory granule membrane 1 ITPR3
Golgi lumen 2 INS, NGF
endoplasmic reticulum lumen 6 ALB, CD4, GCG, IL6, INS, PTGS2
platelet alpha granule lumen 1 ALB
specific granule lumen 1 ARG1
transport vesicle 1 INS
azurophil granule lumen 2 ARG1, TUBB4B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
clathrin-coated endocytic vesicle membrane 1 CD4
Cytoplasm, cytoskeleton, stress fiber 1 MYLK
platelet dense tubular network membrane 1 ITPR3
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
AP-type membrane coat adaptor complex 1 AP1S2
membrane coat 1 AP1S2
Cytoplasmic vesicle, secretory vesicle membrane 1 ITPR3
AP-1 adaptor complex 1 AP1S2
[Glucagon-like peptide 1]: Secreted 1 GCG
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 1 CD4
transport vesicle membrane 1 ITPR3
interleukin-6 receptor complex 1 IL6
cytoplasmic side of endoplasmic reticulum membrane 1 ITPR3
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Lieke C J van den Berk, Bas J H Jansen, Stuart Snowden, Kim G C Siebers-Vermeulen, Christian Gilissen, Gesine Kögler, Carl G Figdor, Craig E Wheelock, Ruurd Torensma. Cord blood mesenchymal stem cells suppress DC-T Cell proliferation via prostaglandin B2. Stem cells and development. 2014 Jul; 23(14):1582-93. doi: 10.1089/scd.2013.0433. [PMID: 24649980]
  • Jeane Silva, Anke Beckedorf, Erhard Bieberich. Osteoblast-derived oxysterol is a migration-inducing factor for human breast cancer cells. The Journal of biological chemistry. 2003 Jul; 278(28):25376-85. doi: 10.1074/jbc.m301233200. [PMID: 12734199]
  • K Büyükgüzel, H Tunaz, S M Putnam, D Stanley. Prostaglandin biosynthesis by midgut tissue isolated from the tobacco hornworm, Manduca sexta. Insect biochemistry and molecular biology. 2002 Apr; 32(4):435-43. doi: 10.1016/s0965-1748(01)00121-7. [PMID: 11886778]
  • N Cattan, D Mary, A Peleraux, B Mari, C Aussel, B Rossi. Prostaglandin B(2) delivers a co-stimulatory signal leading to T cell activation. European cytokine network. 2000 Jun; 11(2):293-9. doi: ". [PMID: 10903809]
  • S Tassin-Moindrot, A Caille, J P Douliez, D Marion, F Vovelle. The wide binding properties of a wheat nonspecific lipid transfer protein. Solution structure of a complex with prostaglandin B2. European journal of biochemistry. 2000 Feb; 267(4):1117-24. doi: 10.1046/j.1432-1327.2000.01109.x. [PMID: 10672021]
  • S Watanabe, T Kobayashi, H Okuyama. Absence of relation between the expression of cyclooxygenase isoforms and the synthesis of prostaglandin E2 in resident and thioglycollate-elicited macrophages in rats. Prostaglandins & other lipid mediators. 1998 May; 56(1):7-18. doi: 10.1016/s0090-6980(98)00039-2. [PMID: 9674017]
  • W S Powell, F Gravelle, S Gravel. Phorbol myristate acetate stimulates the formation of 5-oxo-6,8,11,14-eicosatetraenoic acid by human neutrophils by activating NADPH oxidase. The Journal of biological chemistry. 1994 Oct; 269(41):25373-80. doi: . [PMID: 7929234]
  • S T Ohnishi, A Sakamoto, T Ohnishi, R Ogawa. Inhibition of lipid peroxidation by prostaglandin oligomeric derivatives. Prostaglandins, leukotrienes, and essential fatty acids. 1992 Mar; 45(3):217-21. doi: 10.1016/0952-3278(92)90116-z. [PMID: 1317035]
  • L O Eriksson, B Larsson, H Hedlund, K E Andersson. Prostaglandin E2 binding sites in human renal tissue: characterization and localization by radioligand binding and autoradiography. Acta physiologica Scandinavica. 1990 Jul; 139(3):393-404. doi: 10.1111/j.1748-1716.1990.tb08940.x. [PMID: 2173350]
  • E P Brass, M J Garrity. Structural specificity for prostaglandin effects on hepatocyte glycogenolysis. The Biochemical journal. 1990 Apr; 267(1):59-62. doi: 10.1042/bj2670059. [PMID: 2158311]