Levuglandin D2 (BioDeep_00000009595)

 

Secondary id: BioDeep_00001876830

human metabolite Endogenous


代谢物信息卡片


(5Z,8R,9R,10E,12S)-9-acetyl-8-formyl-12-hydroxyheptadeca-5,10-dienoic acid

化学式: C20H32O5 (352.225)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(plant) 1.54%

分子结构信息

SMILES: CCCCCC(C=CC(C(CC=CCCCC(=O)O)C=O)C(=O)C)O
InChI: InChI=1S/C20H32O5/c1-3-4-7-11-18(23)13-14-19(16(2)22)17(15-21)10-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/t17-,18-,19-/m0/s1

描述信息

Levuglandin D2 is one of the products of a non-enzymatically rearrangement of prostaglandin H2 (PGH2) to this highly reactive gamma-keto aldehyde. PGH2 markedly accelerates the formation of dimers and higher oligomers of amyloid beta1-42. This evidence implicates cyclooxygenase activity in the pathogenesis of Alzheimers disease, and is associated with the formation of levuglandin adducts of the peptide. Levuglandins (LGs) and their stereo and structural isomers are extraordinarily reactive γ-ketoaldehydes that are generated by rearrangements of prostanoid endoperoxide intermediates of polyene cyclooxygenation. Their rapid adduction with biological nucleophiles results, inter alia, in pathological modifications of proteins and DNA. It also complicates their detection. Cyclooxygenase-promoted lipid oxidation is a pivotal step in the biosynthesis of an array of physiologically active metabolites. COX fosters a highly regio and stereoselective cyclooxygenation of arachidonic acid (AA) to deliver a single, enantiomerically pure endoperoxide, PGH2, that is a branch point in the biosynthesis of numerous hormone-like mediators of cellular activities. Spontaneous rearrangements of PGH2 were known to generate prostaglandins (PG) PGD2 and PGE2. (PMID: 12358806, 15752459, 3317517, 10224068) [HMDB]
Levuglandin D2 is one of the products of a non-enzymatically rearrangement of prostaglandin H2 (PGH2) to this highly reactive gamma-keto aldehyde. PGH2 markedly accelerates the formation of dimers and higher oligomers of amyloid beta1-42. This evidence implicates cyclooxygenase activity in the pathogenesis of Alzheimers disease, and is associated with the formation of levuglandin adducts of the peptide. Levuglandins (LGs) and their stereo and structural isomers are extraordinarily reactive γ-ketoaldehydes that are generated by rearrangements of prostanoid endoperoxide intermediates of polyene cyclooxygenation. Their rapid adduction with biological nucleophiles results, inter alia, in pathological modifications of proteins and DNA. It also complicates their detection. Cyclooxygenase-promoted lipid oxidation is a pivotal step in the biosynthesis of an array of physiologically active metabolites. COX fosters a highly regio and stereoselective cyclooxygenation of arachidonic acid (AA) to deliver a single, enantiomerically pure endoperoxide, PGH2, that is a branch point in the biosynthesis of numerous hormone-like mediators of cellular activities. Spontaneous rearrangements of PGH2 were known to generate prostaglandins (PG) PGD2 and PGE2. (PMID: 12358806, 15752459, 3317517, 10224068).

同义名列表

7 个代谢物同义名

(5Z,8R,9R,10E,12S)-9-acetyl-8-formyl-12-hydroxyheptadeca-5,10-dienoic acid; (8R,12R)-9,10-seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid; 9,10-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid; 9,10-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoate; Levuglandin D2; FA 20:4;O3; LGD2



数据库引用编号

16 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)

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

  • Yoshikazu Kanai, Sadahiko Hiroki, Hiroyuki Koshino, Keiichi Konoki, Yuko Cho, Mirriam Cayme, Yasuo Fukuyo, Mari Yotsu-Yamashita. Identification of novel oxidized levuglandin D2 in marine red alga and mouse tissue. Journal of lipid research. 2011 Dec; 52(12):2245-2254. doi: 10.1194/jlr.m017053. [PMID: 21893678]
  • C Chiquet, J Fleury, M Blanc-Jouvan, M Wallon, A Boibieux. [Acquired ocular toxoplasmosis (panuveitis) after liver transplantation]. Journal francais d'ophtalmologie. 2000 Apr; 23(4):375-9. doi: NULL. [PMID: 10794988]