N,N-Dimethylsphingosine (BioDeep_00001874364)
代谢物信息卡片
N,N-Dimethylsphingosine
化学式: C20H41NO2 (327.31371260000003)
中文名称: N,N-二甲基-D-赤型鞘氨醇(PKC抑制剂)
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N(C)C)O
InChI: InChI=1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m0/s1
描述信息
A sphingoid that is sphingosine in which the two amino hydrogens are replaced by methyl groups.
D004791 - Enzyme Inhibitors
同义名列表
1 个代谢物同义名
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:78759
- PubChem: 5282309
- ChEMBL: CHEMBL322333
- CAS: 119567-63-4
- MetaboLights: MTBLC78759
- RefMet: N,N-Dimethylsphingosine
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)
4 个相关的物种来源信息
- 5691 Trypanosoma brucei: 10.1371/JOURNAL.PNTD.0001618
- 3039 Euglena gracilis: 10.3389/FBIOE.2021.662655
- 5691 Trypanosoma brucei: 10.1371/JOURNAL.PNTD.0001618
- 3039 Euglena gracilis: 10.3389/FBIOE.2021.662655
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
- Shy Yang, Jin-Ping Hu, Yan Li. The involvement of blood cells in the phosphorylation of the selective sphingosine-1-phosphate receptor 1 agonist SYL-927.
Die Pharmazie.
2019 02; 74(2):107-110. doi:
10.1691/ph.2019.8809. [PMID: 30782260] - Yan-Chang Lei, Ling-Ling Yang, Wen Li, Pan Luo, Pei-Fen Zheng. Inhibition of sphingosine kinase 1 ameliorates acute liver failure by reducing high-mobility group box 1 cytoplasmic translocation in liver cells.
World journal of gastroenterology.
2015 Dec; 21(46):13055-63. doi:
10.3748/wjg.v21.i46.13055. [PMID: 26676341] - Caroline H Johnson, Gary J Patti, Jean-Philippe Courade, Leah P Shriver, Linh T Hoang, Marianne Manchester, Gary Siuzdak. Alterations in Spinal Cord Metabolism during Treatment of Neuropathic Pain.
Journal of neuroimmune pharmacology : the official journal of the Society on NeuroImmune Pharmacology.
2015 Sep; 10(3):396-401. doi:
10.1007/s11481-015-9624-y. [PMID: 26232265] - Daniel Plano, Shantu Amin, Arun K Sharma. Importance of sphingosine kinase (SphK) as a target in developing cancer therapeutics and recent developments in the synthesis of novel SphK inhibitors.
Journal of medicinal chemistry.
2014 Jul; 57(13):5509-24. doi:
10.1021/jm4011687. [PMID: 24471412] - Li-Wen Lai, Kim-Chong Yong, Yeong-Hau H Lien. Pharmacologic recruitment of regulatory T cells as a therapy for ischemic acute kidney injury.
Kidney international.
2012 May; 81(10):983-992. doi:
10.1038/ki.2011.412. [PMID: 22189844] - Laurence Chan. Harnessing regulatory T cells for therapeutic purposes.
Kidney international.
2012 May; 81(10):935-936. doi:
10.1038/ki.2012.29. [PMID: 22543901] - Tian Lan, Weihua Liu, Xi Xie, Suowen Xu, Kaipeng Huang, Jing Peng, Xiaoyan Shen, Peiqing Liu, Lijing Wang, Pu Xia, Heqing Huang. Sphingosine kinase-1 pathway mediates high glucose-induced fibronectin expression in glomerular mesangial cells.
Molecular endocrinology (Baltimore, Md.).
2011 Dec; 25(12):2094-105. doi:
10.1210/me.2011-0095. [PMID: 21998146] - Keith P Alden, Sandrine Dhondt-Cordelier, Kerrie L McDonald, Theresa J Reape, Carl K-Y Ng, Paul F McCabe, Christopher J Leaver. Sphingolipid long chain base phosphates can regulate apoptotic-like programmed cell death in plants.
Biochemical and biophysical research communications.
2011 Jul; 410(3):574-80. doi:
10.1016/j.bbrc.2011.06.028. [PMID: 21683064] - Joanna M Woodcock, Yuefang Ma, Carl Coolen, Duyen Pham, Claire Jones, Angel F Lopez, Stuart M Pitson. Sphingosine and FTY720 directly bind pro-survival 14-3-3 proteins to regulate their function.
Cellular signalling.
2010 Sep; 22(9):1291-9. doi:
10.1016/j.cellsig.2010.04.004. [PMID: 20403428] - Robert A McDonald, Susan Pyne, Nigel J Pyne, Anne Grant, Cherry L Wainwright, Roger M Wadsworth. The sphingosine kinase inhibitor N,N-dimethylsphingosine inhibits neointimal hyperplasia.
British journal of pharmacology.
2010 Feb; 159(3):543-53. doi:
10.1111/j.1476-5381.2009.00533.x. [PMID: 20015089] - Antonina Kolmakova, Mohanraj Rajesh, David Zang, Roberto Pili, Subroto Chatterjee. VEGF recruits lactosylceramide to induce endothelial cell adhesion molecule expression and angiogenesis in vitro and in vivo.
Glycoconjugate journal.
2009 Jul; 26(5):547-58. doi:
10.1007/s10719-008-9206-9. [PMID: 19219548] - Michael ter Braak, Kerstin Danneberg, Karin Lichte, Kerstin Liphardt, Nicholas T Ktistakis, Stuart M Pitson, Timothy Hla, Karl H Jakobs, Dagmar Meyer zu Heringdorf. Galpha(q)-mediated plasma membrane translocation of sphingosine kinase-1 and cross-activation of S1P receptors.
Biochimica et biophysica acta.
2009 May; 1791(5):357-70. doi:
10.1016/j.bbalip.2009.01.019. [PMID: 19830907] - David R Gude, Sergio E Alvarez, Steven W Paugh, Poulami Mitra, JiaDe Yu, Rachael Griffiths, Suzanne E Barbour, Sheldon Milstien, Sarah Spiegel. Apoptosis induces expression of sphingosine kinase 1 to release sphingosine-1-phosphate as a "come-and-get-me" signal.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2008 Aug; 22(8):2629-38. doi:
10.1096/fj.08-107169. [PMID: 18362204] - Ji-Yeong Jo, Hyo-Lim Kim, Yun-Kyung Lee, Hideaki Tomura, Yoe-Sik Bae, Fumikazu Okajima, Dong-Soon Im. N,N-Dimethyl-D-erythro-sphingosine inhibits store-operated Ca2+ entry in U937 monocytes.
Journal of pharmacological sciences.
2008 Jul; 107(3):303-7. doi:
10.1254/jphs.08078fp. [PMID: 18635921] - Hyo-Lim Kim, Mijin Han, Dong-Soon Im. Differential signaling of sphingosine derivatives in U937 human monocytes depends on the degree of N-methylation.
Prostaglandins & other lipid mediators.
2008 Jun; 86(1-4):68-72. doi:
10.1016/j.prostaglandins.2008.03.003. [PMID: 18467142] - Hyo-Lim Kim, Santosh J Sacket, Mijin Han, Dong-Soon Im. Characterization of N,N,-dimethyl-D-erythro-sphingosine-induced apoptosis and signaling in U937 cells: independence of sphingosine kinase inhibition.
Prostaglandins & other lipid mediators.
2008 Jun; 86(1-4):18-25. doi:
10.1016/j.prostaglandins.2008.01.001. [PMID: 18316219] - You-Xun Jin, Hwan-Soo Yoo, Akio Kihara, Chang-Hwan Choi, Seikwan Oh, Dong-Cheul Moon, Yasuyuki Igarashi, Yong-Moon Lee. Sphingosine kinase assay system with fluorescent detection in high performance liquid chromatography.
Archives of pharmacal research.
2006 Nov; 29(11):1049-54. doi:
10.1007/bf02969290. [PMID: 17146975] - Yun-Kyung Lee, Young-Jin Im, Yu-Lee Kim, Dong-Soon Im. Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes.
Biochemical and biophysical research communications.
2006 Sep; 348(3):1116-22. doi:
10.1016/j.bbrc.2006.07.164. [PMID: 16904073] - Harsimran S Saini, Rochelle P Coelho, Sravan K Goparaju, Puneet S Jolly, Michael Maceyka, Sarah Spiegel, Carmen Sato-Bigbee. Novel role of sphingosine kinase 1 as a mediator of neurotrophin-3 action in oligodendrocyte progenitors.
Journal of neurochemistry.
2005 Dec; 95(5):1298-310. doi:
10.1111/j.1471-4159.2005.03451.x. [PMID: 16313513] - Andreas Billich, Frédéric Bornancin, Diana Mechtcheriakova, François Natt, Dieter Huesken, Thomas Baumruker. Basal and induced sphingosine kinase 1 activity in A549 carcinoma cells: function in cell survival and IL-1beta and TNF-alpha induced production of inflammatory mediators.
Cellular signalling.
2005 Oct; 17(10):1203-17. doi:
10.1016/j.cellsig.2004.12.005. [PMID: 16038795] - Fu-Xu Wang, Zuo-Ren Dong, Ze-Lin Liu, Ling Pan, Jian-Min Luo, Xue-Jun Zhang, Hong-Ling Hao, Xiao-Ling Li, Jing-Ci Yang, Ling-Ling Jiang. mitochondrial ceramidase overexpression up-regulates Bcl-2 protein level in K562 cells, probably through its metabolite sphingosine-1-phosphate.
Zhongguo shi yan xue ye xue za zhi.
2004 Oct; 12(5):577-83. doi:
. [PMID: 15498114] - Sven C D Van IJzendoorn, Johanna M Van Der Wouden, Gerhard Liebisch, Gerd Schmitz, Dick Hoekstra. Polarized membrane traffic and cell polarity development is dependent on dihydroceramide synthase-regulated sphinganine turnover.
Molecular biology of the cell.
2004 Sep; 15(9):4115-24. doi:
10.1091/mbc.e04-04-0290. [PMID: 15229289] - Carole A Welsch, Lukas W A Roth, Jean François Goetschy, N Rao Movva. Genetic, biochemical, and transcriptional responses of Saccharomyces cerevisiae to the novel immunomodulator FTY720 largely mimic those of the natural sphingolipid phytosphingosine.
The Journal of biological chemistry.
2004 Aug; 279(35):36720-31. doi:
10.1074/jbc.m406179200. [PMID: 15190065] - Hai-Feng Duan, Chu-Tse Wu, Ying Lu, Hua Wang, Hong-Jun Liu, Qun-Wei Zhang, Xiang-Xu Jia, Zhu-Zhuang Lu, Li-Sheng Wang. Sphingosine kinase activation regulates hepatocyte growth factor induced migration of endothelial cells.
Experimental cell research.
2004 Aug; 298(2):593-601. doi:
10.1016/j.yexcr.2004.04.049. [PMID: 15265705] - Tilla S Worgall, Rebecca A Juliano, Toru Seo, Richard J Deckelbaum. Ceramide synthesis correlates with the posttranscriptional regulation of the sterol-regulatory element-binding protein.
Arteriosclerosis, thrombosis, and vascular biology.
2004 May; 24(5):943-8. doi:
10.1161/01.atv.0000125703.20434.4d. [PMID: 15132973] - Norio Hanafusa, Yutaka Yatomi, Koei Yamada, Yuichi Hori, Masaomi Nangaku, Toshihiro Okuda, Toshiro Fujita, Kiyoshi Kurokawa, Masafumi Fukagawa. Sphingosine 1-phosphate stimulates rat mesangial cell proliferation from outside the cells.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2002 Apr; 17(4):580-6. doi:
10.1093/ndt/17.4.580. [PMID: 11917049] - O Cuvillier, T Levade. Sphingosine 1-phosphate antagonizes apoptosis of human leukemia cells by inhibiting release of cytochrome c and Smac/DIABLO from mitochondria.
Blood.
2001 Nov; 98(9):2828-36. doi:
10.1182/blood.v98.9.2828. [PMID: 11675357] - J S Karliner, N Honbo, K Summers, M O Gray, E J Goetzl. The lysophospholipids sphingosine-1-phosphate and lysophosphatidic acid enhance survival during hypoxia in neonatal rat cardiac myocytes.
Journal of molecular and cellular cardiology.
2001 Sep; 33(9):1713-7. doi:
10.1006/jmcc.2001.1429. [PMID: 11549349] - Y Osawa, M Nagaki, Y Banno, Y Nozawa, H Moriwaki, S Nakashima. Sphingosine kinase regulates hepatoma cell differentiation: roles of hepatocyte nuclear factor and retinoid receptor.
Biochemical and biophysical research communications.
2001 Aug; 286(4):673-7. doi:
10.1006/bbrc.2001.5451. [PMID: 11520048] - 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] - K W Young, M D Bootman, D R Channing, P Lipp, P R Maycox, J Meakin, R A Challiss, S R Nahorski. Lysophosphatidic acid-induced Ca2+ mobilization requires intracellular sphingosine 1-phosphate production. Potential involvement of endogenous EDG-4 receptors.
The Journal of biological chemistry.
2000 Dec; 275(49):38532-9. doi:
10.1074/jbc.m006631200. [PMID: 10954727] - H Okamoto, Y Yatomi, T Ohmori, K Satoh, Y Matsumoto, Y Ozaki. Sphingosine 1-phosphate stimulates G(i)- and Rho-mediated vascular endothelial cell spreading and migration.
Thrombosis research.
2000 Aug; 99(3):259-65. doi:
10.1016/s0049-3848(00)00251-6. [PMID: 10942792] - F Y Chuang, M Sassaroli, J C Unkeless. Convergence of Fc gamma receptor IIA and Fc gamma receptor IIIB signaling pathways in human neutrophils.
Journal of immunology (Baltimore, Md. : 1950).
2000 Jan; 164(1):350-60. doi:
10.4049/jimmunol.164.1.350. [PMID: 10605030] - C Sharma, T Smith, S Li, G J Schroepfer, D H Needleman. Inhibition of Ca2+ release channel (ryanodine receptor) activity by sphingolipid bases: mechanism of action.
Chemistry and physics of lipids.
2000 Jan; 104(1):1-11. doi:
10.1016/s0009-3084(99)00106-1. [PMID: 10660207] - A Olivera, T Kohama, L Edsall, V Nava, O Cuvillier, S Poulton, S Spiegel. Sphingosine kinase expression increases intracellular sphingosine-1-phosphate and promotes cell growth and survival.
The Journal of cell biology.
1999 Nov; 147(3):545-58. doi:
10.1083/jcb.147.3.545. [PMID: 10545499] - L Cavallini, R Venerando, G Miotto, A Alexandre. Ganglioside GM1 protection from apoptosis of rat heart fibroblasts.
Archives of biochemistry and biophysics.
1999 Oct; 370(2):156-62. doi:
10.1006/abbi.1999.1378. [PMID: 10510273] - L C Edsall, J R Van Brocklyn, O Cuvillier, B Kleuser, S Spiegel. N,N-Dimethylsphingosine is a potent competitive inhibitor of sphingosine kinase but not of protein kinase C: modulation of cellular levels of sphingosine 1-phosphate and ceramide.
Biochemistry.
1998 Sep; 37(37):12892-8. doi:
10.1021/bi980744d. [PMID: 9737868] - C Caldwell, V Norman, A Urbina, A Jarvis, C Quinonez, M Stemm, A S Dahms. Regulatory differences among avian ecto-ATPases.
Biochemical and biophysical research communications.
1997 Sep; 238(3):728-32. doi:
10.1006/bbrc.1997.7377. [PMID: 9325157] - E A Sweeney, C Sakakura, T Shirahama, A Masamune, H Ohta, S Hakomori, Y Igarashi. Sphingosine and its methylated derivative N,N-dimethylsphingosine (DMS) induce apoptosis in a variety of human cancer cell lines.
International journal of cancer.
1996 May; 66(3):358-66. doi:
10.1002/(sici)1097-0215(19960503)66:3<358::aid-ijc16>3.0.co;2-7. [PMID: 8621258] - B Lau, P M Macdonald. Determination of the pKa of membrane-bound N,N-dimethylsphingosine using deuterium NMR spectroscopy.
Biochimica et biophysica acta.
1995 Jul; 1237(1):37-42. doi:
10.1016/0005-2736(95)00083-f. [PMID: 7619840] - K Uemura, A Hara, T Taketomi. Inhibition of neurite outgrowth in neuroblastoma cells by sphingosine.
Journal of biochemistry.
1993 Oct; 114(4):610-4. doi:
10.1093/oxfordjournals.jbchem.a124225. [PMID: 8276777] - B Felding-Habermann, Y Igarashi, B A Fenderson, L S Park, N S Radin, J Inokuchi, G Strassmann, K Handa, S Hakomori. A ceramide analogue inhibits T cell proliferative response through inhibition of glycosphingolipid synthesis and enhancement of N,N-dimethylsphingosine synthesis.
Biochemistry.
1990 Jul; 29(26):6314-22. doi:
10.1021/bi00478a028. [PMID: 2207076] - . .
.
. doi:
. [PMID: 10751414]