Delta-12-Prostaglandin J2 (BioDeep_00000006017)

Main id: BioDeep_00000629371

 

human metabolite Endogenous blood metabolite


代谢物信息卡片


(5Z)-7-[(1S,5E)-5-[(3S)-3-hydroxyoctylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid

化学式: C20H30O4 (334.214398)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCC(CC=C1C(C=CC1=O)CC=CCCCC(=O)O)O
InChI: InChI=1S/C20H30O4/c1-2-3-6-10-17(21)13-14-18-16(12-15-19(18)22)9-7-4-5-8-11-20(23)24/h4,7,12,14-17,21H,2-3,5-6,8-11,13H2,1H3,(H,23,24)/b7-4-,18-14+/t16-,17-/m0/s1

描述信息

Delta-12-Prostaglandin J2 (d12-PGJ2) is the ultimate metabolite of Prostaglandin D2 (PGD2). PGD2 is an unstable molecule and undergoes dehydration to form PGJ2 in aqueous solution, and is then converted to d12-PGJ2, in the presence of serum albumin or plasma. d12-PGJ2 forms a conjugate with the thiol of glutathione (GSH) and GSH suppresses the d12-PGJ2-induced HSP synthesis and subsequent inhibition of cell growth (HSPs are a set of proteins synthesized in response to heat shock or to other environmental stresses). d12-PGJ2 has been shown to stimulate alkaline phosphatase activity and calcification of human osteoblastic cells, the potency of the PGs being comparable to that of 1-a,25-dihydroxy vitamin D. d12-PGJ2 enhances the type-1 collagen synthesis in human osteoblasts during calcification. Thus, d12-PGJ2 modulates osteogenesis through induction of the syntheses of multiple proteins related to mineralization. Considering that PGD2 is a major arachidonate metabolite in bone marrow, d12-PGJ2, may be physiologically involved in the modulation of osteogenesis. d12-PGJ2 induces heme oxygenase, HO-l. Heme oxygenase is a key enzyme in heme catabolism, oxidatively clearing heme to yield biliverdin, iron and carbon monoxide. The biological function of this enzyme is the conversion of potentially toxic heme to bile and the recovery of the iron. Furthermore, carbon monoxide produced on the enzymatic degradation of heme has been suggested to function as a neural messenger. Two isozymes of heme oxygenase, HO-l and HO-2, have been identified. HO-2 is constitutively expressed, while HO-l is drastically induced in response to a variety of stresses, including heavy metals, heat shock and UV irradiation. (PMID: 8777585)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.
delta-12-Prostaglandin J2 (d12-PGJ2) is the ultimate metabolite of Prostaglandin D2 (PGD2). PGD2 is an unstable molecule and undergoes dehydration to form PGJ2 in aqueous solution, and is then converted to d12-PGJ2, in the presence of serum albumin or plasma. d12-PGJ2 forms a conjugate with the thiol of glutathione (GSH) and GSH suppresses the d12-PGJ2-induced HSP synthesis and subsequent inhibition of cell growth (HSPs are a set of proteins synthesized in response to heat shock or to other environmental stresses). d12-PGJ2 has been shown to stimulate alkaline phosphatase activity and calcification of human osteoblastic cells, the potency of the PGs being comparable to that of 1-a,25-dihydroxy vitamin D. d12-PGJ2 enhances the type-1 collagen synthesis in human osteoblasts during calcification. Thus, d12-PGJ2 modulates osteogenesis through induction of the syntheses of multiple proteins related to mineralization. Considering that PGD2 is a major arachidonate metabolite in bone marrow, d12-PGJ2, may be physiologically involved in the modulation of osteogenesis. d12-PGJ2 induces heme oxygenase, HO-l. Heme oxygenase is a key enzyme in heme catabolism, oxidatively clearing heme to yield biliverdin, iron and carbon monoxide. The biological function of this enzyme is the conversion of potentially toxic heme to bile and the recovery of the iron. Furthermore, carbon monoxide produced on the enzymatic degradation of heme has been suggested to function as a neural messenger. Two isozymes of heme oxygenase, HO-l and HO-2, have been identified. HO-2 is constitutively expressed, while HO-l is drastically induced in response to a variety of stresses, including heavy metals, heat shock and UV irradiation. (PMID: 8777585)
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
D000970 - Antineoplastic Agents

同义名列表

18 个代谢物同义名

(5Z)-7-[(1S,5E)-5-[(3S)-3-hydroxyoctylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid; 7-[5-(3-hydroxyoctylidene)-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid; 9-Deoxy-9,10-didehydro-12,13-didehydro-13,14-dihydroprostaglandin D2; (5Z,12E,15S)-15-Hydroxy-11-oxo-prosta-5,9,12-trien-1-Oic acid; 9-Deoxy-delta(9), delta(12)-13,14-dihydroprostaglandin D2; 11-oxo-15S-hydroxy-prosta-5Z,9,12E-trien-1-oic acid; 9-Deoxy-δ(9), δ(12)-13,14-dihydroprostaglandin D2; 9-Deoxy-delta(9,12)-13,14-dihydro PGD2; 9-Deoxy-δ(9,12)-13,14-dihydro PGD2; delta-12-Prostaglandin J2; Δ-12-prostaglandin J2; Prostaglandin J2; delta(12)-PGJ2; delta-12-PGJ2; Δ(12)-PGJ2; Δ-12-PGJ2; DDDD-PGD2; D12-PGJ2



数据库引用编号

17 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

54 个相关的代谢反应过程信息。

Reactome(5)

BioCyc(0)

WikiPathways(3)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

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

  • Wolfgang Neuhofer, Konstantin Holzapfel, Maria-Luisa Fraek, Nengtai Ouyang, Jens Lutz, Franz-X Beck. Chronic COX-2 inhibition reduces medullary HSP70 expression and induces papillary apoptosis in dehydrated rats. Kidney international. 2004 Feb; 65(2):431-41. doi: 10.1111/j.1523-1755.2004.00387.x. [PMID: 14717913]
  • Akos Heinemann, Rufina Schuligoi, Ian Sabroe, Adele Hartnell, Bernhard A Peskar. Delta 12-prostaglandin J2, a plasma metabolite of prostaglandin D2, causes eosinophil mobilization from the bone marrow and primes eosinophils for chemotaxis. Journal of immunology (Baltimore, Md. : 1950). 2003 May; 170(9):4752-8. doi: 10.4049/jimmunol.170.9.4752. [PMID: 12707356]
  • E F Mc Clay. The effects of Delta(12)-PGJ(2) on malignant cells. Prostaglandins & other lipid mediators. 2000 Jun; 62(1):75-90. doi: 10.1016/s0090-6980(00)00076-9. [PMID: 10936416]
  • K W Marvin, R L Eykholt, J A Keelan, T A Sato, M D Mitchell. The 15-deoxy-delta(12,14)-prostaglandin J(2)receptor, peroxisome proliferator activated receptor-gamma (PPARgamma) is expressed in human gestational tissues and is functionally active in JEG3 choriocarcinoma cells. Placenta. 2000 May; 21(4):436-40. doi: 10.1053/plac.1999.0485. [PMID: 10833383]
  • D H Wright, K M Metters, M Abramovitz, A W Ford-Hutchinson. Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist. British journal of pharmacology. 1998 Apr; 123(7):1317-24. doi: 10.1038/sj.bjp.0701708. [PMID: 9579725]
  • S Fukushima, S Kishimoto, Y Takeuchi, M Fukushima, M Suzuki, K Furuta, R Noyori, H Sasaki, Y Kikuchi, M Nakano, S Kurozumi. [Pharmaceutical and pharmacological development of antitumor prostaglandins]. Nihon rinsho. Japanese journal of clinical medicine. 1998 Mar; 56(3):663-9. doi: . [PMID: 9549353]
  • C Amici, A T Palamara, E Garaci, M G Santoro. Inhibition of Sendai virus replication by delta 12-prostaglandin J2: induction of heat shock protein synthesis and alteration of protein glycosylation. Antiviral research. 1992 Aug; 19(2):129-38. doi: 10.1016/0166-3542(92)90072-d. [PMID: 1332600]
  • G Nishimura. [Antitumor activity and cell cycle effects of delta 12-PGJ2 in vivo]. Nihon Gan Chiryo Gakkai shi. 1990 Mar; 25(3):632-9. doi: . [PMID: 2351856]
  • Y Kikawa, S Narumiya, M Fukushima, H Wakatsuka, O Hayaishi. 9-Deoxy-delta 9, delta 12-13,14-dihydroprostaglandin D2, a metabolite of prostaglandin D2 formed in human plasma. Proceedings of the National Academy of Sciences of the United States of America. 1984 Mar; 81(5):1317-21. doi: 10.1073/pnas.81.5.1317. [PMID: 6584883]