Prostaglandin B2 (BioDeep_00000004024)
Secondary id: BioDeep_00000405082
human metabolite Endogenous blood metabolite natural product
代谢物信息卡片
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%
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
- ChEBI: CHEBI:28099
- KEGG: C05954
- PubChem: 5280881
- HMDB: HMDB0004236
- Metlin: METLIN3466
- DrugBank: DB02304
- ChEMBL: CHEMBL1901620
- foodb: FDB023342
- chemspider: 4450370
- CAS: 13367-85-6
- PMhub: MS000014725
- LipidMAPS: LMFA03010018
- 3DMET: B01928
- NIKKAJI: J16.062H
- RefMet: PGB2
- PubChem: 8238
- KNApSAcK: 28099
- LOTUS: LTS0067136
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)
- Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA
- Metabolism of lipids:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Fatty acid metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi
- Arachidonic acid metabolism:
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
- Synthesis of Prostaglandins (PG) and Thromboxanes (TX):
H+ + e- + prostaglandin G2 ⟶ H2O + prostaglandin H2
BioCyc(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(46)
- Arachidonic Acid Metabolism:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Leukotriene C4 Synthesis Deficiency:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Piroxicam Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Acetylsalicylic Acid Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Etodolac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Ketoprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Ibuprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Rofecoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Diclofenac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Sulindac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Celecoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Ketorolac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Suprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Bromfenac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Indomethacin Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Mefenamic Acid Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Oxaprozin Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Nabumetone Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Naproxen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Diflunisal Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Meloxicam Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Valdecoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Antipyrine Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Antrafenine Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Carprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Etoricoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Fenoprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Flurbiprofen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Magnesium Salicylate Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Lumiracoxib Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Lornoxicam Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Phenylbutazone Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Nepafenac Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Trisalicylate-Choline Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Tolmetin Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Tiaprofenic Acid Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Tenoxicam Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Salsalate Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Salicylate-Sodium Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Salicylic Acid Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Acetaminophen Action Pathway:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Arachidonic Acid Metabolism:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Leukotriene C4 Synthesis Deficiency:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Arachidonic Acid Metabolism:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Arachidonic Acid Metabolism:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
- Leukotriene C4 Synthesis Deficiency:
Glutathione + Leukotriene A4 ⟶ Leukotriene C4
PharmGKB(0)
23 个相关的物种来源信息
- 40678 - Alcyoniidae: LTS0067136
- 6101 - Anthozoa: LTS0067136
- 7711 - Chordata: LTS0067136
- 6073 - Cnidaria: LTS0067136
- 2759 - Eukaryota: LTS0067136
- 9604 - Hominidae: LTS0067136
- 9605 - Homo: LTS0067136
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1038/NBT.2488
- 9606 - Homo sapiens: LTS0067136
- 3325 - Larix: LTS0067136
- 62751 - Larix sibirica: 10.1007/BF00598571
- 62751 - Larix sibirica: LTS0067136
- 40674 - Mammalia: LTS0067136
- 33208 - Metazoa: LTS0067136
- 3318 - Pinaceae: LTS0067136
- 58019 - Pinopsida: LTS0067136
- 51812 - Sarcophyton: LTS0067136
- 358797 - Sarcophyton crassocaule: 10.1021/NP990205P
- 358797 - Sarcophyton crassocaule: LTS0067136
- 35493 - Streptophyta: LTS0067136
- 58023 - Tracheophyta: LTS0067136
- 33090 - Viridiplantae: LTS0067136
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
- 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]