N-[(1R,2R,3E)-2-hydroxy-1-(hydroxymethyl)heptadec-3-en-1-yl]acetamide (BioDeep_00000857429)

   


代谢物信息卡片


N-[(1R,2R,3E)-2-hydroxy-1-(hydroxymethyl)heptadec-3-en-1-yl]acetamide

化学式: C20H39NO3 (341.29297840000004)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCCCCCCC=CC(C(CO)NC(=O)C)O
InChI: InChI=1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20-/m1/s1

描述信息

同义名列表

1 个代谢物同义名

N-[(1R,2R,3E)-2-hydroxy-1-(hydroxymethyl)heptadec-3-en-1-yl]acetamide



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代谢反应

0 个相关的代谢反应过程信息。

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INOH(0)

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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

  • Micah M Ross, Ted B Piorczynski, Jamison Harvey, Tyson S Burnham, Morgan Francis, Madison W Larsen, Kyle Roe, Jason M Hansen, Michael R Stark. Ceramide: a novel inducer for neural tube defects. Developmental dynamics : an official publication of the American Association of Anatomists. 2019 10; 248(10):979-996. doi: 10.1002/dvdy.93. [PMID: 31390103]
  • L Shi, D Banerjee, A Dobierzewska, S Sathishkumar, A A Karakashian, N V Giltiay, M N Nikolova-Karakashian. Direct regulation of IGF-binding protein 1 promoter by interleukin-1β via an insulin- and FoxO-1-independent mechanism. American journal of physiology. Endocrinology and metabolism. 2016 Apr; 310(8):E612-E623. doi: 10.1152/ajpendo.00289.2015. [PMID: 26884383]
  • Zhihui Zhu, Rongyu Li, Rolf Stricker, Georg Reiser. Extracellular α-crystallin protects astrocytes from cell death through activation of MAPK, PI3K/Akt signaling pathway and blockade of ROS release from mitochondria. Brain research. 2015 Sep; 1620(?):17-28. doi: 10.1016/j.brainres.2015.05.011. [PMID: 25998538]
  • Hideo Ogiso, Makoto Taniguchi, Toshiro Okazaki. Analysis of lipid-composition changes in plasma membrane microdomains. Journal of lipid research. 2015 Aug; 56(8):1594-605. doi: 10.1194/jlr.m059972. [PMID: 26116739]
  • Luigi Leanza, Paul O'Reilly, Anne Doyle, Elisa Venturini, Mario Zoratti, Eva Szegezdi, Ildiko Szabo. Correlation between potassium channel expression and sensitivity to drug-induced cell death in tumor cell lines. Current pharmaceutical design. 2014; 20(2):189-200. doi: 10.2174/13816128113199990032. [PMID: 23701546]
  • H Li, Y Zhou, A Zhao, Y Qiu, G Xie, Q Jiang, X Zheng, W Zhong, X Sun, Z Zhou, W Jia. Asymmetric dimethylarginine attenuates serum starvation-induced apoptosis via suppression of the Fas (APO-1/CD95)/JNK (SAPK) pathway. Cell death & disease. 2013 Oct; 4(?):e830. doi: 10.1038/cddis.2013.345. [PMID: 24091673]
  • Hideyuki Iwayama, Norishi Ueda. Role of mitochondrial Bax, caspases, and MAPKs for ceramide-induced apoptosis in renal proximal tubular cells. Molecular and cellular biochemistry. 2013 Jul; 379(1-2):37-42. doi: 10.1007/s11010-013-1624-8. [PMID: 23543151]
  • Tim Ting Chiu, Yi Sun, Alexandra Koshkina, Amira Klip. Rac-1 superactivation triggers insulin-independent glucose transporter 4 (GLUT4) translocation that bypasses signaling defects exerted by c-Jun N-terminal kinase (JNK)- and ceramide-induced insulin resistance. The Journal of biological chemistry. 2013 Jun; 288(24):17520-31. doi: 10.1074/jbc.m113.467647. [PMID: 23640896]
  • Mark J Dekker, Chris Baker, Mark Naples, Josh Samsoondar, Rianna Zhang, Wei Qiu, Jennifer Sacco, Khosrow Adeli. Inhibition of sphingolipid synthesis improves dyslipidemia in the diet-induced hamster model of insulin resistance: evidence for the role of sphingosine and sphinganine in hepatic VLDL-apoB100 overproduction. Atherosclerosis. 2013 May; 228(1):98-109. doi: 10.1016/j.atherosclerosis.2013.01.041. [PMID: 23466071]
  • Chin Siang Kue, Mi Young Jung, Daeho Cho, Tae Sung Kim. C6-ceramide enhances Interleukin-12-mediated T helper type 1 cell responses through a cyclooxygenase-2-dependent pathway. Immunobiology. 2012 Jun; 217(6):601-9. doi: 10.1016/j.imbio.2011.10.021. [PMID: 22112438]
  • Anjaneyulu Kowluru. Friendly, and not so friendly, roles of Rac1 in islet β-cell function: lessons learnt from pharmacological and molecular biological approaches. Biochemical pharmacology. 2011 Apr; 81(8):965-75. doi: 10.1016/j.bcp.2011.01.013. [PMID: 21300027]
  • William Weidong Du, Burton B Yang, Bing L Yang, Zhaoqun Deng, Ling Fang, Sze Wan Shan, Zina Jeyapalan, Yaou Zhang, Arun Seth, Albert J Yee. Versican G3 domain modulates breast cancer cell apoptosis: a mechanism for breast cancer cell response to chemotherapy and EGFR therapy. PloS one. 2011; 6(11):e26396. doi: 10.1371/journal.pone.0026396. [PMID: 22096483]
  • Isabelle Martins, Antoine Tesniere, Oliver Kepp, Mickael Michaud, Frederic Schlemmer, Laura Senovilla, Claire Séror, Didier Métivier, Jean-Luc Perfettini, Laurence Zitvogel, Guido Kroemer. Chemotherapy induces ATP release from tumor cells. Cell cycle (Georgetown, Tex.). 2009 Nov; 8(22):3723-8. doi: 10.4161/cc.8.22.10026. [PMID: 19855167]
  • Lellean JeBailey, Oshrit Wanono, Wenyan Niu, Jessica Roessler, Assaf Rudich, Amira Klip. Ceramide- and oxidant-induced insulin resistance involve loss of insulin-dependent Rac-activation and actin remodeling in muscle cells. Diabetes. 2007 Feb; 56(2):394-403. doi: 10.2337/db06-0823. [PMID: 17259384]
  • Cynthia Detre, Endre Kiss, Zoltán Varga, Katalin Ludányi, Katalin Pászty, Agnes Enyedi, Dorottya Kövesdi, György Panyi, Eva Rajnavölgyi, János Matkó. Death or survival: membrane ceramide controls the fate and activation of antigen-specific T-cells depending on signal strength and duration. Cellular signalling. 2006 Mar; 18(3):294-306. doi: 10.1016/j.cellsig.2005.05.012. [PMID: 16099142]
  • R Goswami, D Singh, G Phillips, J Kilkus, G Dawson. Ceramide regulation of the tumor suppressor phosphatase PTEN in rafts isolated from neurotumor cell lines. Journal of neuroscience research. 2005 Aug; 81(4):541-50. doi: 10.1002/jnr.20550. [PMID: 15968641]
  • Paul Gutwein, Alexander Stoeck, Svenja Riedle, Daniela Gast, Steffen Runz, Thomas P Condon, Alexander Marmé, Minh-Chau Phong, Otwin Linderkamp, Alexander Skorokhod, Peter Altevogt. Cleavage of L1 in exosomes and apoptotic membrane vesicles released from ovarian carcinoma cells. Clinical cancer research : an official journal of the American Association for Cancer Research. 2005 Apr; 11(7):2492-501. doi: 10.1158/1078-0432.ccr-04-1688. [PMID: 15814625]
  • Lu-Cheng Cao, Thomas W Honeyman, Rachel Cooney, Lori Kennington, Cheryl R Scheid, Julie A Jonassen. Mitochondrial dysfunction is a primary event in renal cell oxalate toxicity. Kidney international. 2004 Nov; 66(5):1890-900. doi: 10.1111/j.1523-1755.2004.00963.x. [PMID: 15496160]
  • Erika Suzuki, Kazuko Handa, Marcos S Toledo, Senitiroh Hakomori. Sphingosine-dependent apoptosis: a unified concept based on multiple mechanisms operating in concert. Proceedings of the National Academy of Sciences of the United States of America. 2004 Oct; 101(41):14788-93. doi: 10.1073/pnas.0406536101. [PMID: 15466700]
  • Pamela J Mansfield, Shannon S Carey, Vania Hinkovska-Galcheva, James A Shayman, Laurence A Boxer. Ceramide inhibition of phospholipase D and its relationship to RhoA and ARF1 translocation in GTP gamma S-stimulated polymorphonuclear leukocytes. Blood. 2004 Mar; 103(6):2363-8. doi: 10.1182/blood-2002-11-3341. [PMID: 14615385]
  • C M Perks, P V Newcomb, M Grohmann, R J Wright, H D Mason, J M P Holly. Prolactin acts as a potent survival factor against C2-ceramide-induced apoptosis in human granulosa cells. Human reproduction (Oxford, England). 2003 Dec; 18(12):2672-7. doi: 10.1093/humrep/deg496. [PMID: 14645190]
  • Scott R Witting, J Nicholas Maiorano, W Sean Davidson. Ceramide enhances cholesterol efflux to apolipoprotein A-I by increasing the cell surface presence of ATP-binding cassette transporter A1. The Journal of biological chemistry. 2003 Oct; 278(41):40121-7. doi: 10.1074/jbc.m305193200. [PMID: 12890677]
  • Xue Qing Wang, Ai Ying Xiao, Christian Sheline, Krzystztof Hyrc, Aizhen Yang, Mark P Goldberg, Dennis W Choi, Shan Ping Yu. Apoptotic insults impair Na+, K+-ATPase activity as a mechanism of neuronal death mediated by concurrent ATP deficiency and oxidant stress. Journal of cell science. 2003 May; 116(Pt 10):2099-110. doi: 10.1242/jcs.00420. [PMID: 12679386]
  • Brad L Upham, Tyler R Koski, Alisa M Rummel, Melinda R Wilson, Anelia Horvath, James E Trosko. Differential roles of 2, 6, and 8 carbon ceramides on the modulation of gap junctional communication and apoptosis during carcinogenesis. Cancer letters. 2003 Feb; 191(1):27-34. doi: 10.1016/s0304-3835(02)00620-1. [PMID: 12609706]
  • S Willaime-Morawek, K Brami-Cherrier, J Mariani, J Caboche, B Brugg. C-Jun N-terminal kinases/c-Jun and p38 pathways cooperate in ceramide-induced neuronal apoptosis. Neuroscience. 2003; 119(2):387-97. doi: 10.1016/s0306-4522(02)00996-x. [PMID: 12770554]
  • Leah J Siskind, Richard N Kolesnick, Marco Colombini. Ceramide channels increase the permeability of the mitochondrial outer membrane to small proteins. The Journal of biological chemistry. 2002 Jul; 277(30):26796-803. doi: 10.1074/jbc.m200754200. [PMID: 12006562]
  • Pamela J Mansfield, Vania Hinkovska-Galcheva, James A Shayman, Laurence A Boxer. Granulocyte colony-stimulating factor primes NADPH oxidase in neutrophils through translocation of cytochrome b(558) by gelatinase-granule release. The Journal of laboratory and clinical medicine. 2002 Jul; 140(1):9-16. doi: 10.1067/mlc.2002.124551. [PMID: 12080323]
  • Rachelle E Toman, Vilen Movsesyan, Shvetha K Murthy, Sheldon Milstien, Sarah Spiegel, Alan I Faden. Ceramide-induced cell death in primary neuronal cultures: upregulation of ceramide levels during neuronal apoptosis. Journal of neuroscience research. 2002 May; 68(3):323-30. doi: 10.1002/jnr.10190. [PMID: 12111862]
  • Laura Colombaioni, Laura M Frago, Isabel Varela-Nieto, Rossana Pesi, Mercedes Garcia-Gil. Serum deprivation increases ceramide levels and induces apoptosis in undifferentiated HN9.10e cells. Neurochemistry international. 2002 Apr; 40(4):327-36. doi: 10.1016/s0197-0186(01)00090-0. [PMID: 11792463]
  • Atsuko Itakura, Akane Tanaka, Akihiro Aioi, Hiroshi Tonogaito, Hiroshi Matsuda. Ceramide and sphingosine rapidly induce apoptosis of murine mast cells supported by interleukin-3 and stem cell factor. Experimental hematology. 2002 Mar; 30(3):272-8. doi: 10.1016/s0301-472x(01)00790-1. [PMID: 11882365]
  • Pamela J Mansfield, Vania Hinkovska-Galcheva, Shannon S Carey, James A Shayman, Laurence A Boxer. Regulation of polymorphonuclear leukocyte degranulation and oxidant production by ceramide through inhibition of phospholipase D. Blood. 2002 Feb; 99(4):1434-41. doi: 10.1182/blood.v99.4.1434. [PMID: 11830497]
  • Abdelkarim Abousalham, Tom C Hobman, Jay Dewald, Michael Garbutt, David N Brindley. Cell-permeable ceramides preferentially inhibit coated vesicle formation and exocytosis in Chinese hamster ovary compared with Madin-Darby canine kidney cells by preventing the membrane association of ADP-ribosylation factor. The Biochemical journal. 2002 Feb; 361(Pt 3):653-61. doi: 10.1042/0264-6021:3610653. [PMID: 11802796]
  • M Todaro, M Catalano, D Di Liberto, M Patti, M Zerilli, F Di Gaudio, G Di Gesù, G Vetri, G Modica, A Bono, M Ciaccio, Giorgio Stassi. High levels of exogenous C2-ceramide promote morphological and biochemical evidences of necrotic features in thyroid follicular cells. Journal of cellular biochemistry. 2002; 86(1):162-73. doi: 10.1002/jcb.10203. [PMID: 12112027]
  • D K Kim, E S Cho, J K Seong, H D Um. Adaptive concentrations of hydrogen peroxide suppress cell death by blocking the activation of SAPK/JNK pathway. Journal of cell science. 2001 Dec; 114(Pt 23):4329-34. doi: 10.1242/jcs.114.23.4329. [PMID: 11739664]
  • N Vitale, A S Caumont, S Chasserot-Golaz, G Du, S Wu, V A Sciorra, A J Morris, M A Frohman, M F Bader. Phospholipase D1: a key factor for the exocytotic machinery in neuroendocrine cells. The EMBO journal. 2001 May; 20(10):2424-34. doi: 10.1093/emboj/20.10.2424. [PMID: 11350931]
  • L C Edsall, O Cuvillier, S Twitty, S Spiegel, S Milstien. Sphingosine kinase expression regulates apoptosis and caspase activation in PC12 cells. Journal of neurochemistry. 2001 Mar; 76(5):1573-84. doi: 10.1046/j.1471-4159.2001.00164.x. [PMID: 11238741]
  • T Kajimoto, S Ohmori, Y Shirai, N Sakai, N Saito. Subtype-specific translocation of the delta subtype of protein kinase C and its activation by tyrosine phosphorylation induced by ceramide in HeLa cells. Molecular and cellular biology. 2001 Mar; 21(5):1769-83. doi: 10.1128/mcb.21.5.1769-1783.2001. [PMID: 11238914]
  • E Hajduch, A Balendran, I H Batty, G J Litherland, A S Blair, C P Downes, H S Hundal. Ceramide impairs the insulin-dependent membrane recruitment of protein kinase B leading to a loss in downstream signalling in L6 skeletal muscle cells. Diabetologia. 2001 Feb; 44(2):173-83. doi: 10.1007/s001250051596. [PMID: 11270673]
  • M P Muriel, N Lambeng, F Darios, P P Michel, E C Hirsch, Y Agid, M Ruberg. Mitochondrial free calcium levels (Rhod-2 fluorescence) and ultrastructural alterations in neuronally differentiated PC12 cells during ceramide-dependent cell death. The Journal of comparative neurology. 2000 Oct; 426(2):297-315. doi: 10.1002/1096-9861(20001016)426:2<297::aid-cne10>3.0.co;2-o. [PMID: 10982470]
  • P Navarro, A M Valverde, J L Rohn, M Benito, M Lorenzo. Akt mediates insulin rescue from apoptosis in brown adipocytes: effect of ceramide. Growth hormone & IGF research : official journal of the Growth Hormone Research Society and the International IGF Research Society. 2000 Oct; 10(5):256-66. doi: 10.1054/ghir.2000.0165. [PMID: 11042022]
  • C Menné, J P Lauritsen, J Dietrich, J Kastrup, A M Wegener, N Odum, C Geisler. Ceramide-induced TCR up-regulation. Journal of immunology (Baltimore, Md. : 1950). 2000 Sep; 165(6):3065-72. doi: 10.4049/jimmunol.165.6.3065. [PMID: 10975817]
  • A Di Nardo, L Benassi, C Magnoni, A Cossarizza, S Seidenari, A Giannetti. Ceramide 2 (N-acetyl sphingosine) is associated with reduction in Bcl-2 protein levels by Western blotting and with apoptosis in cultured human keratinocytes. The British journal of dermatology. 2000 Sep; 143(3):491-7. doi: 10.1111/j.1365-2133.2000.03700.x. [PMID: 10971319]
  • Y Sautin, N Takamura, S Shklyaev, Y Nagayama, A Ohtsuru, H Namba, S Yamashita. Ceramide-induced apoptosis of human thyroid cancer cells resistant to apoptosis by irradiation. Thyroid : official journal of the American Thyroid Association. 2000 Sep; 10(9):733-40. doi: 10.1089/thy.2000.10.733. [PMID: 11041449]
  • K A Meadows, J M Holly, C E Stewart. Tumor necrosis factor-alpha-induced apoptosis is associated with suppression of insulin-like growth factor binding protein-5 secretion in differentiating murine skeletal myoblasts. Journal of cellular physiology. 2000 Jun; 183(3):330-7. doi: 10.1002/(sici)1097-4652(200006)183:3<330::aid-jcp5>3.0.co;2-n. [PMID: 10797307]
  • H S Kim, D B Hausman, M M Compton, R G Dean, R J Martin, G J Hausman, D L Hartzell, C A Baile. Induction of apoptosis by all-trans-retinoic acid and C2-ceramide treatment in rat stromal-vascular cultures. Biochemical and biophysical research communications. 2000 Apr; 270(1):76-80. doi: 10.1006/bbrc.2000.2373. [PMID: 10733907]
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  • R Mihai, T Lai, G Schofield, J R Farndon. C2-Ceramide increases cytoplasmic calcium concentrations in human parathyroid cells. Biochemical and biophysical research communications. 2000 Feb; 268(2):636-41. doi: 10.1006/bbrc.2000.2159. [PMID: 10679256]
  • M Salinas, R López-Valdaliso, D Martín, A Alvarez, A Cuadrado. Inhibition of PKB/Akt1 by C2-ceramide involves activation of ceramide-activated protein phosphatase in PC12 cells. Molecular and cellular neurosciences. 2000 Feb; 15(2):156-69. doi: 10.1006/mcne.1999.0813. [PMID: 10673324]
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