10-Nitrolinoleic acid (BioDeep_00000002822)
Secondary id: BioDeep_00001874766
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C18H31NO4 (325.22529660000004)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 40%
分子结构信息
SMILES: CCCCC/C=C\C/C(=C\CCCCCCCC(=O)O)/[N+](=O)[O-]
InChI: InChI=1S/C18H31NO4/c1-2-3-4-5-8-11-14-17(19(22)23)15-12-9-6-7-10-13-16-18(20)21/h8,11,15H,2-7,9-10,12-14,16H2,1H3,(H,20,21)
描述信息
Nitrolinoleic acid is a nitrated fatty acid (or nitroalkene, a class of cell signaling mediators generated by Nitric Oxide (NO) and fatty acid-dependent redox reactions). Nitrated fatty acids such as 10- and 12-nitro-9,12-octadecadienoic acid exhibit pluripotent antiinflammatory cell signaling properties. (PMID 16537525) [HMDB]
Nitrolinoleic acid is a nitrated fatty acid (or nitroalkene, a class of cell signaling mediators generated by Nitric Oxide (NO) and fatty acid-dependent redox reactions). Nitrated fatty acids such as 10- and 12-nitro-9,12-octadecadienoic acid exhibit pluripotent antiinflammatory cell signaling properties. (PMID 16537525).
同义名列表
19 个代谢物同义名
(9E,12Z)-10-Nitrooctadeca-9,12-dienoic acid; 10-Nitro-9-cis,12-cis-octadecadienoic acid; (9E,12Z)-10-Nitrooctadeca-9,12-dienoate; 10-Nitro-9-cis,12-cis-octadecadienoate; 10-nitro-9Z,12Z-octadecadienoic acid; 10-Nitro-9,12-octadecadienoic acid; 12-Nitro-9,12-octadecadienoic acid; 10-Nitro,9Z,12Z-octadecadienoate; 12-Nitro-9,12-octadecadienoate; 10-Nitro-9,12-octadecadienoate; 10-Nitrolinoleic acid; 9-Nitrolinoleic acid; Nitrolinoleic acid; 10-Nitrolinoleate; 774603-04-2; C10-LNO2; LNO2 CPD; 9-HODE; LNO2
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:34125
- KEGG: C13800
- PubChem: 5282259
- PubChem: 656744
- HMDB: HMDB0005049
- LipidMAPS: LMFA01120001
- foodb: FDB023611
- chemspider: 4445433
- CAS: 774603-04-2
- PMhub: MS000006109
- PubChem: 854045
- PDB-CCD: LNA
- 3DMET: B04581
- NIKKAJI: J2.402.207B
- RefMet: 10-Nitrolinoleic acid
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
- Qiongju Qiu, Giancarlo Abis, Florence Mattingly-Peck, Steven Lynham, Franca Fraternali, Maria R Conte. Allosteric Regulation of the Soluble Epoxide Hydrolase by Nitro Fatty Acids: a Combined Experimental and Computational Approach.
Journal of molecular biology.
2022 09; 434(17):167600. doi:
10.1016/j.jmb.2022.167600. [PMID: 35460669] - Tanja K Rudolph, Thorben Ravekes, Anna Klinke, Kai Friedrichs, Martin Mollenhauer, Michaela Pekarova, Gabriela Ambrozova, Hana Martiskova, Jatinder-Jit Kaur, Bianca Matthes, Alex Schwoerer, Steven R Woodcock, Lukas Kubala, Bruce A Freeman, Stephan Baldus, Volker Rudolph. Nitrated fatty acids suppress angiotensin II-mediated fibrotic remodelling and atrial fibrillation.
Cardiovascular research.
2016 Jan; 109(1):174-84. doi:
10.1093/cvr/cvv254. [PMID: 26598510] - Xiaochun Tang, Yanhong Guo, Kae Nakamura, Huarong Huang, Milton Hamblin, Lin Chang, Luis Villacorta, Kejie Yin, Hongsheng Ouyang, Jifeng Zhang. Nitroalkenes induce rat aortic smooth muscle cell apoptosis via activation of caspase-dependent pathways.
Biochemical and biophysical research communications.
2010 Jun; 397(2):239-44. doi:
10.1016/j.bbrc.2010.05.091. [PMID: 20493166] - Marcienne M Wright, Junghyun Kim, Thomas D Hock, Norbert Leitinger, Bruce A Freeman, Anupam Agarwal. Human haem oxygenase-1 induction by nitro-linoleic acid is mediated by cAMP, AP-1 and E-box response element interactions.
The Biochemical journal.
2009 Aug; 422(2):353-61. doi:
10.1042/bj20090339. [PMID: 19534727] - Paola Manini, Luigia Capelli, Samantha Reale, Marianna Arzillo, Orlando Crescenzi, Alessandra Napolitano, Vincenzo Barone, Marco d'Ischia. Chemistry of nitrated lipids: remarkable instability of 9-nitrolinoleic acid in neutral aqueous medium and a novel nitronitrate ester product by concurrent autoxidation/nitric oxide-release pathways.
The Journal of organic chemistry.
2008 Oct; 73(19):7517-25. doi:
10.1021/jo801364v. [PMID: 18767799] - Richard L Alexander, Darcy J P Bates, Marcus W Wright, S Bruce King, Charles S Morrow. Modulation of nitrated lipid signaling by multidrug resistance protein 1 (MRP1): glutathione conjugation and MRP1-mediated efflux inhibit nitrolinoleic acid-induced, PPARgamma-dependent transcription activation.
Biochemistry.
2006 Jun; 45(25):7889-96. doi:
10.1021/bi0605639. [PMID: 16784241] - Emersom S Lima, Marcelo G Bonini, Ohara Augusto, Hermes V Barbeiro, Heraldo P Souza, Dulcineia S P Abdalla. Nitrated lipids decompose to nitric oxide and lipid radicals and cause vasorelaxation.
Free radical biology & medicine.
2005 Aug; 39(4):532-9. doi:
10.1016/j.freeradbiomed.2005.04.005. [PMID: 16043024] - Francisco J Schopfer, Paul R S Baker, Gregory Giles, Phil Chumley, Carlos Batthyany, Jack Crawford, Rakesh P Patel, Neil Hogg, Bruce P Branchaud, Jack R Lancaster, Bruce A Freeman. Fatty acid transduction of nitric oxide signaling. Nitrolinoleic acid is a hydrophobically stabilized nitric oxide donor.
The Journal of biological chemistry.
2005 May; 280(19):19289-97. doi:
10.1074/jbc.m414689200. [PMID: 15764811]