9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- (BioDeep_00000175401)
human metabolite blood metabolite
代谢物信息卡片
9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-
化学式: C20H39NO2 (325.2981)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCCCCC=CCCCCCCCC(O)=NCCO
InChI: InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)
描述信息
同义名列表
数据库引用编号
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。
| 亚细胞结构定位 | 关联基因列表 |
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文献列表
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Disease models & mechanisms.
2012 Sep; 5(5):660-70. doi:
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2011 Jul; 52(7):1373-82. doi:
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European journal of pharmacology.
2011 Jun; 660(2-3):305-9. doi:
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2011 May; 52(5):1011-22. doi:
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2011 Mar; 96(3):787-91. doi:
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2011 Mar; 60(4):593-601. doi:
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2010; 17(14):1450-67. doi:
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Journal of molecular and cellular cardiology.
2010 Jan; 48(1):201-10. doi:
10.1016/j.yjmcc.2009.07.011. [PMID: 19616555] - L Jean-Gilles, S Feng, C R Tench, V Chapman, D A Kendall, D A Barrett, C S Constantinescu. Plasma endocannabinoid levels in multiple sclerosis.
Journal of the neurological sciences.
2009 Dec; 287(1-2):212-5. doi:
10.1016/j.jns.2009.07.021. [PMID: 19695579] - Sivaram Pillarisetti, Christopher W Alexander, Ish Khanna. Pain and beyond: fatty acid amides and fatty acid amide hydrolase inhibitors in cardiovascular and metabolic diseases.
Drug discovery today.
2009 Dec; 14(23-24):1098-111. doi:
10.1016/j.drudis.2009.08.002. [PMID: 19716430] - Grzegorz Godlewski, László Offertáler, Jens A Wagner, George Kunos. Receptors for acylethanolamides-GPR55 and GPR119.
Prostaglandins & other lipid mediators.
2009 Sep; 89(3-4):105-11. doi:
10.1016/j.prostaglandins.2009.07.001. [PMID: 19615459] - Dong-Soon Im. New intercellular lipid mediators and their GPCRs: an update.
Prostaglandins & other lipid mediators.
2009 Sep; 89(3-4):53-6. doi:
10.1016/j.prostaglandins.2009.01.002. [PMID: 19442546] - Matthew N Hill, Gregory E Miller, Erica J Carrier, Boris B Gorzalka, Cecilia J Hillard. Circulating endocannabinoids and N-acyl ethanolamines are differentially regulated in major depression and following exposure to social stress.
Psychoneuroendocrinology.
2009 Sep; 34(8):1257-62. doi:
10.1016/j.psyneuen.2009.03.013. [PMID: 19394765] - María Martínez de Ubago, Inmaculada García-Oya, Antonio Pérez-Pérez, Alberto Canfrán-Duque, Rocio Quintana-Portillo, Fernando Rodríguez de Fonseca, Carmen González-Yanes, Víctor Sánchez-Margalet. Oleoylethanolamide, a natural ligand for PPAR-alpha, inhibits insulin receptor signalling in HTC rat hepatoma cells.
Biochimica et biophysica acta.
2009 Aug; 1791(8):740-5. doi:
10.1016/j.bbalip.2009.03.014. [PMID: 19345745] - Joe Palandra, Jeff Prusakiewicz, Josef S Ozer, Yanhua Zhang, Timothy G Heath. Endogenous ethanolamide analysis in human plasma using HPLC tandem MS with electrospray ionization.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2009 Jul; 877(22):2052-60. doi:
10.1016/j.jchromb.2009.05.043. [PMID: 19535304] - Giulio G Muccioli, Angela Sia, Paul J Muchowski, Nephi Stella. Genetic manipulation of palmitoylethanolamide production and inactivation in Saccharomyces cerevisiae.
PloS one.
2009 Jun; 4(6):e5942. doi:
10.1371/journal.pone.0005942. [PMID: 19529773] - Frédéric Darios, Catherine Wasser, Anastasia Shakirzyanova, Artur Giniatullin, Kerry Goodman, Jose L Munoz-Bravo, Jesica Raingo, Jernej Jorgacevski, Marko Kreft, Robert Zorec, Juliana M Rosa, Luis Gandia, Luis M Gutiérrez, Thomas Binz, Rashid Giniatullin, Ege T Kavalali, Bazbek Davletov. Sphingosine facilitates SNARE complex assembly and activates synaptic vesicle exocytosis.
Neuron.
2009 Jun; 62(5):683-94. doi:
10.1016/j.neuron.2009.04.024. [PMID: 19524527] - Stefania Petrosino, Alessia Ligresti, Vincenzo Di Marzo. Endocannabinoid chemical biology: a tool for the development of novel therapies.
Current opinion in chemical biology.
2009 Jun; 13(3):309-20. doi:
10.1016/j.cbpa.2009.04.616. [PMID: 19457702] - Hong Lan, Galya Vassileva, Aaron Corona, Li Liu, Hana Baker, Andrei Golovko, Susan J Abbondanzo, Weiwen Hu, Shijun Yang, Yun Ning, Robert A Del Vecchio, Frederique Poulet, Maureen Laverty, Eric L Gustafson, Joseph A Hedrick, Timothy J Kowalski. GPR119 is required for physiological regulation of glucagon-like peptide-1 secretion but not for metabolic homeostasis.
The Journal of endocrinology.
2009 May; 201(2):219-30. doi:
10.1677/joe-08-0453. [PMID: 19282326] - Lina M Lauffer, Roman Iakoubov, Patricia L Brubaker. GPR119 is essential for oleoylethanolamide-induced glucagon-like peptide-1 secretion from the intestinal enteroendocrine L-cell.
Diabetes.
2009 May; 58(5):1058-66. doi:
10.2337/db08-1237. [PMID: 19208912] - Dagmar Koethe, Andrea Giuffrida, Daniela Schreiber, Martin Hellmich, Frauke Schultze-Lutter, Stefan Ruhrmann, Joachim Klosterkötter, Daniele Piomelli, F Markus Leweke. Anandamide elevation in cerebrospinal fluid in initial prodromal states of psychosis.
The British journal of psychiatry : the journal of mental science.
2009 Apr; 194(4):371-2. doi:
10.1192/bjp.bp.108.053843. [PMID: 19336792] - N L Cluny, C M Keenan, B Lutz, D Piomelli, K A Sharkey. The identification of peroxisome proliferator-activated receptor alpha-independent effects of oleoylethanolamide on intestinal transit in mice.
Neurogastroenterology and motility.
2009 Apr; 21(4):420-9. doi:
10.1111/j.1365-2982.2008.01248.x. [PMID: 19140957] - Dagmar Koethe, Daniela Schreiber, Andrea Giuffrida, Christian Mauss, Johannes Faulhaber, Bernd Heydenreich, Martin Hellmich, Rudolf Graf, Joachim Klosterkötter, Daniele Piomelli, F Markus Leweke. Sleep deprivation increases oleoylethanolamide in human cerebrospinal fluid.
Journal of neural transmission (Vienna, Austria : 1996).
2009 Mar; 116(3):301-5. doi:
10.1007/s00702-008-0169-6. [PMID: 19137236] - O I Voĭtychuk, V S Asmolkova, N M Hula, H V Sotkis, M Oz, Ia M Shuba. [Regulation of the excitability of neonatal cardiomyocytes by N-stearoyl- and N-oleoyl-ethanolamines].
Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994).
2009; 55(3):55-66. doi:
NULL. [PMID: 19526857] - Miriam Melis, Giuliano Pillolla, Antonio Luchicchi, Anna Lisa Muntoni, Sevil Yasar, Steven R Goldberg, Marco Pistis. Endogenous fatty acid ethanolamides suppress nicotine-induced activation of mesolimbic dopamine neurons through nuclear receptors.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2008 Dec; 28(51):13985-94. doi:
10.1523/jneurosci.3221-08.2008. [PMID: 19091987] - Ruben Nogueiras, Christelle Veyrat-Durebex, Paula M Suchanek, Marcella Klein, Johannes Tschöp, Charles Caldwell, Stephen C Woods, Gabor Wittmann, Masahiko Watanabe, Zsolt Liposits, Csaba Fekete, Ofer Reizes, Francoise Rohner-Jeanrenaud, Matthias H Tschöp. Peripheral, but not central, CB1 antagonism provides food intake-independent metabolic benefits in diet-induced obese rats.
Diabetes.
2008 Nov; 57(11):2977-91. doi:
10.2337/db08-0161. [PMID: 18716045] - F E Lithander, C M Strik, A-T McGill, A K MacGibbon, B H McArdle, S D Poppitt. No effect of an oleoylethanolamide-related phospholipid on satiety and energy intake: a randomised controlled trial of phosphatidylethanolamine.
Lipids in health and disease.
2008 Oct; 7(?):41. doi:
10.1186/1476-511x-7-41. [PMID: 18957134] - Gary J Schwartz, Jin Fu, Giuseppe Astarita, Xiaosong Li, Silvana Gaetani, Patrizia Campolongo, Vincenzo Cuomo, Daniele Piomelli. The lipid messenger OEA links dietary fat intake to satiety.
Cell metabolism.
2008 Oct; 8(4):281-288. doi:
10.1016/j.cmet.2008.08.005. [PMID: 18840358] - Clémentine Thabuis, Delphine Tissot-Favre, Jean-Baptiste Bezelgues, Jean-Charles Martin, Cristina Cruz-Hernandez, Fabiola Dionisi, Frédéric Destaillats. Biological functions and metabolism of oleoylethanolamide.
Lipids.
2008 Oct; 43(10):887-94. doi:
10.1007/s11745-008-3217-y. [PMID: 18704536] - S Gaetani, W H Kaye, V Cuomo, D Piomelli. Role of endocannabinoids and their analogues in obesity and eating disorders.
Eating and weight disorders : EWD.
2008 Sep; 13(3):e42-8. doi:
NULL. [PMID: 19011363] - Clémentine Thabuis, Delphine Tissot-Favre, Jean-Baptiste Bezelgues, Jean-Charles Martin, Cristina Cruz-Hernandez, Fabiola Dionisi, Frédéric Destaillats. Analysis of chemically synthesized oleoylethanolamide by gas-liquid chromatography.
Journal of chromatography. A.
2008 Aug; 1202(2):216-9. doi:
10.1016/j.chroma.2008.07.008. [PMID: 18644599] - Michael Webb, Lin Luo, Jing Ying Ma, Chui-Se Tham. Genetic deletion of Fatty Acid Amide Hydrolase results in improved long-term outcome in chronic autoimmune encephalitis.
Neuroscience letters.
2008 Jul; 439(1):106-10. doi:
10.1016/j.neulet.2008.04.090. [PMID: 18501510] - Jin Fu, Janet Kim, Fariba Oveisi, Giuseppe Astarita, Daniele Piomelli. Targeted enhancement of oleoylethanolamide production in proximal small intestine induces across-meal satiety in rats.
American journal of physiology. Regulatory, integrative and comparative physiology.
2008 Jul; 295(1):R45-50. doi:
10.1152/ajpregu.00126.2008. [PMID: 18434444] - F J Pavón, A Serrano, V Pérez-Valero, N Jagerovic, L Hernández-Folgado, F J Bermúdez-Silva, M Macías, P Goya, F R de Fonseca. Central versus peripheral antagonism of cannabinoid CB1 receptor in obesity: effects of LH-21, a peripherally acting neutral cannabinoid receptor antagonist, in Zucker rats.
Journal of neuroendocrinology.
2008 May; 20 Suppl 1(?):116-23. doi:
10.1111/j.1365-2826.2008.01693.x. [PMID: 18426510] - Akihiro Asakawa, Megumi Toyoshima, Kouji H Harada, Mineko Fujimiya, Kayoko Inoue, Akio Koizumi. The ubiquitous environmental pollutant perfluorooctanoicacid inhibits feeding behavior via peroxisome proliferator-activated receptor-alpha.
International journal of molecular medicine.
2008 Apr; 21(4):439-45. doi:
10.3892/ijmm.21.4.439. [PMID: 18360689] - Andreas Artmann, Gitte Petersen, Lars I Hellgren, Julie Boberg, Christian Skonberg, Christine Nellemann, Steen Honoré Hansen, Harald S Hansen. Influence of dietary fatty acids on endocannabinoid and N-acylethanolamine levels in rat brain, liver and small intestine.
Biochimica et biophysica acta.
2008 Apr; 1781(4):200-12. doi:
10.1016/j.bbalip.2008.01.006. [PMID: 18316044] - Jun Wang, Natsuo Ueda. Role of the endocannabinoid system in metabolic control.
Current opinion in nephrology and hypertension.
2008 Jan; 17(1):1-10. doi:
10.1097/mnh.0b013e3282f29071. [PMID: 18090663] - Antonia Serrano, Ignacio Del Arco, Francisco Javier Pavón, Manuel Macías, Vidal Perez-Valero, Fernando Rodríguez de Fonseca. The cannabinoid CB1 receptor antagonist SR141716A (Rimonabant) enhances the metabolic benefits of long-term treatment with oleoylethanolamide in Zucker rats.
Neuropharmacology.
2008 Jan; 54(1):226-34. doi:
10.1016/j.neuropharm.2007.03.007. [PMID: 17467748] - Giovanna Zolese, Tiziana Bacchetti, Simona Masciangelo, Letizia Ragni, Simona Ambrosi, Annarina Ambrosini, Milvia Marini, Gianna Ferretti. Effect of acylethanolamides on lipid peroxidation and paraoxonase activity.
BioFactors (Oxford, England).
2008; 33(3):201-9. doi:
10.1002/biof.5520330306. [PMID: 19478424] - Margarita Suardíaz, Guillermo Estivill-Torrús, Carlos Goicoechea, Ainhoa Bilbao, Fernando Rodríguez de Fonseca. Analgesic properties of oleoylethanolamide (OEA) in visceral and inflammatory pain.
Pain.
2007 Dec; 133(1-3):99-110. doi:
10.1016/j.pain.2007.03.008. [PMID: 17449181] - R G Pertwee. GPR55: a new member of the cannabinoid receptor clan?.
British journal of pharmacology.
2007 Dec; 152(7):984-6. doi:
10.1038/sj.bjp.0707464. [PMID: 17876300] - S E O'Sullivan. Cannabinoids go nuclear: evidence for activation of peroxisome proliferator-activated receptors.
British journal of pharmacology.
2007 Nov; 152(5):576-82. doi:
10.1038/sj.bjp.0707423. [PMID: 17704824] - Didier M Lambert, Giulio G Muccioli. Endocannabinoids and related N-acylethanolamines in the control of appetite and energy metabolism: emergence of new molecular players.
Current opinion in clinical nutrition and metabolic care.
2007 Nov; 10(6):735-44. doi:
10.1097/mco.0b013e3282f00061. [PMID: 18089956] - Eric Murillo-Rodríguez, Edgar Vázquez, Diana Millán-Aldaco, Marcela Palomero-Rivero, René Drucker-Colin. Effects of the fatty acid amide hydrolase inhibitor URB597 on the sleep-wake cycle, c-Fos expression and dopamine levels of the rat.
European journal of pharmacology.
2007 May; 562(1-2):82-91. doi:
10.1016/j.ejphar.2007.01.076. [PMID: 17336288] - Jin Fu, Giuseppe Astarita, Silvana Gaetani, Janet Kim, Benjamin F Cravatt, Ken Mackie, Daniele Piomelli. Food intake regulates oleoylethanolamide formation and degradation in the proximal small intestine.
The Journal of biological chemistry.
2007 Jan; 282(2):1518-28. doi:
10.1074/jbc.m607809200. [PMID: 17121838] - Yingkui Yang, Min Chen, Keith E Georgeson, Carroll M Harmon. Mechanism of oleoylethanolamide on fatty acid uptake in small intestine after food intake and body weight reduction.
American journal of physiology. Regulatory, integrative and comparative physiology.
2007 Jan; 292(1):R235-41. doi:
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