Levuglandin E2 (BioDeep_00000009594)
Secondary id: BioDeep_00001883841
human metabolite Endogenous
代谢物信息卡片
化学式: C20H32O5 (352.225)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(lipidomics) 11.92%
分子结构信息
SMILES: C(O)(=O)CCC/C=C\C[C@@H](C(=O)C)[C@H](C=O)/C=C/[C@@H](O)CCCCC
InChI: InChI=1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(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 E2 is a levuglandin generated in the cyclooxygenase (COX) pathway. 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: 15752459) [HMDB]
Levuglandin E2 is a levuglandin generated in the cyclooxygenase (COX) pathway. 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: 15752459).
同义名列表
7 个代谢物同义名
(5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid; (8R,12R)-10,11-seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid; 10,11-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid; 10,11-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoate; Levuglandin E2; FA 20:4;O3; LGE2
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:34821
- KEGG: C13807
- PubChem: 53420919
- PubChem: 5282261
- PubChem: 5771742
- HMDB: HMDB0002363
- Metlin: METLIN36373
- Metlin: METLIN58125
- Wikipedia: Levuglandin
- LipidMAPS: LMFA03100001
- foodb: FDB022979
- chemspider: 30776554
- CAS: 91712-41-3
- PMhub: MS000023389
- PubChem: 854052
- 3DMET: B04583
- NIKKAJI: J316.465I
- RefMet: LGE2
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
- Lisa Longato, Fausto Andreola, Sean S Davies, Jackson L Roberts, Giuseppe Fusai, Massimo Pinzani, Kevin Moore, Krista Rombouts. Reactive gamma-ketoaldehydes as novel activators of hepatic stellate cells in vitro.
Free radical biology & medicine.
2017 01; 102(?):162-173. doi:
10.1016/j.freeradbiomed.2016.11.036. [PMID: 27890721] - Bharathi Govindarajan, James Laird, Robert G Salomon, Sanjoy K Bhattacharya. Isolevuglandin-modified proteins, including elevated levels of inactive calpain-1, accumulate in glaucomatous trabecular meshwork.
Biochemistry.
2008 Jan; 47(2):817-25. doi:
10.1021/bi701517m. [PMID: 18085799] - Sean S Davies, Venkataraman Amarnath, Cynthia J Brame, Olivier Boutaud, L Jackson Roberts. Measurement of chronic oxidative and inflammatory stress by quantification of isoketal/levuglandin gamma-ketoaldehyde protein adducts using liquid chromatography tandem mass spectrometry.
Nature protocols.
2007; 2(9):2079-91. doi:
10.1038/nprot.2007.298. [PMID: 17853863] - Sean S Davies, Eric J Brantley, Paul A Voziyan, Venkataraman Amarnath, Irene Zagol-Ikapitte, Olivier Boutaud, Billy G Hudson, John A Oates, L Jackson Roberts. Pyridoxamine analogues scavenge lipid-derived gamma-ketoaldehydes and protect against H2O2-mediated cytotoxicity.
Biochemistry.
2006 Dec; 45(51):15756-67. doi:
10.1021/bi061860g. [PMID: 17176098] - Irene Zagol-Ikapitte, Tina S Masterson, V Amarnath, Thomas J Montine, Katrin I Andreasson, Olivier Boutaud, John A Oates. Prostaglandin H(2)-derived adducts of proteins correlate with Alzheimer's disease severity.
Journal of neurochemistry.
2005 Aug; 94(4):1140-5. doi:
10.1111/j.1471-4159.2005.03264.x. [PMID: 15992375] - Robert G Salomon. Distinguishing levuglandins produced through the cyclooxygenase and isoprostane pathways.
Chemistry and physics of lipids.
2005 Mar; 134(1):1-20. doi:
10.1016/j.chemphyslip.2004.12.003. [PMID: 15752459] - Robert G Salomon. Levuglandins and isolevuglandins: stealthy toxins of oxidative injury.
Antioxidants & redox signaling.
2005 Jan; 7(1-2):185-201. doi:
10.1089/ars.2005.7.185. [PMID: 15650407] - Irene Zagol-Ikapitte, Nathalie Bernoud-Hubac, Venkataraman Amarnath, L Jackson Roberts, Olivier Boutaud, John A Oates. Characterization of bis(levuglandinyl) urea derivatives as products of the reaction between prostaglandin H2 and arginine.
Biochemistry.
2004 May; 43(18):5503-10. doi:
10.1021/bi049842r. [PMID: 15122916] - Sean S Davies, Megha Talati, Xiahong Wang, Raymond L Mernaugh, Venkataraman Amarnath, Joshua Fessel, Barbara O Meyrick, James Sheller, L Jackson Roberts. Localization of isoketal adducts in vivo using a single-chain antibody.
Free radical biology & medicine.
2004 May; 36(9):1163-74. doi:
10.1016/j.freeradbiomed.2004.02.014. [PMID: 15082070] - R G Salomon, E Batyreva, K Kaur, D L Sprecher, M J Schreiber, J W Crabb, M S Penn, A M DiCorletoe, S L Hazen, E A Podrez. Isolevuglandin-protein adducts in humans: products of free radical-induced lipid oxidation through the isoprostane pathway.
Biochimica et biophysica acta.
2000 May; 1485(2-3):225-35. doi:
10.1016/s1388-1981(00)00038-x. [PMID: 10832102] - R G Salomon, W Sha, C Brame, K Kaur, G Subbanagounder, J O'Neil, H F Hoff, L J Roberts. Protein adducts of iso[4]levuglandin E2, a product of the isoprostane pathway, in oxidized low density lipoprotein.
The Journal of biological chemistry.
1999 Jul; 274(29):20271-80. doi:
10.1074/jbc.274.29.20271. [PMID: 10400646] - R G Salomon, G Subbanagounder, U Singh, J O'Neil, H F Hoff. Oxidation of low-density lipoproteins produces levuglandin-protein adducts.
Chemical research in toxicology.
1997 Jul; 10(7):750-9. doi:
10.1021/tx970016b. [PMID: 9250408] - R G Salomon, G Subbanagounder, J O'Neil, K Kaur, M A Smith, H F Hoff, G Perry, V M Monnier. Levuglandin E2-protein adducts in human plasma and vasculature.
Chemical research in toxicology.
1997 May; 10(5):536-45. doi:
10.1021/tx960157y. [PMID: 9168251] - E DiFranco, G Subbanagounder, S Kim, K Murthi, S Taneda, V M Monnier, R G Salomon. Formation and stability of pyrrole adducts in the reaction of levuglandin E2 with proteins.
Chemical research in toxicology.
1995 Jan; 8(1):61-7. doi:
10.1021/tx00043a008. [PMID: 7703368] - R G Salomon, M R Jirousek, S Ghosh, R B Sharma. Prostaglandin endoperoxides 21. Covalent binding of levuglandin E2 with proteins.
Prostaglandins.
1987 Nov; 34(5):643-56. doi:
10.1016/0090-6980(87)90289-9. [PMID: 3481092]
