N-Hexanoylsphingosine (BioDeep_00001028389)

   


代谢物信息卡片


N-(hexanoyl)sphing-4-enine

化学式: C24H47NO3 (397.3555752)
中文名称: N-己酰基-D-赤型鞘氨醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCCCCCCCCC=CC(C(CO)NC(=O)CCCCC)O
InChI: InChI=1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+/t22-,23+/m0/s1

描述信息

同义名列表

2 个代谢物同义名

N-(hexanoyl)sphing-4-enine; N-Hexanoylsphingosine



数据库引用编号

4 个数据库交叉引用编号

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)

0 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

  • Nicolas Coant, John D Bickel, Ronald Rahaim, Yuka Otsuka, Yong-Mi Choi, Ruijuan Xu, Michael Simoes, Chris Cariello, Cungui Mao, Essa M Saied, Christoph Arenz, Timothy P Spicer, Thomas D Bannister, Peter J Tonge, Michael V Airola, Louis Scampavia, Yusuf A Hannun, Robert C Rizzo, John D Haley. Neutral ceramidase-active site inhibitor chemotypes and binding modes. Bioorganic chemistry. 2023 10; 139(?):106747. doi: 10.1016/j.bioorg.2023.106747. [PMID: 37531819]
  • Yang Liu, Rui Shao, Tongchuan Suo, Junjie Zhu, Erwei Liu, Yajing Wang, Lin Miao, Xiumei Gao. Traditional Chinese Medicine Danzhi qing'e decoction inhibits inflammation-associated prostatic hyperplasia via inactivation of ERK1/2 signal pathway. Journal of ethnopharmacology. 2023 Jun; 309(?):116354. doi: 10.1016/j.jep.2023.116354. [PMID: 36906158]
  • Lingling Xuan, Feifei Han, Lili Gong, Yali Lv, Zirui Wan, He Liu, Lulu Ren, Song Yang, Wen Zhang, Ting Li, Chunting Tan, Lihong Liu. Ceramide induces MMP-9 expression through JAK2/STAT3 pathway in airway epithelium. Lipids in health and disease. 2020 Aug; 19(1):196. doi: 10.1186/s12944-020-01373-w. [PMID: 32829707]
  • Francesca Zanieri, Ana Levi, David Montefusco, Lisa Longato, Francesco De Chiara, Luca Frenguelli, Sara Omenetti, Fausto Andreola, Tu Vinh Luong, Veronica Massey, Juan Caballeria, Constantino Fondevila, Sriram S Shanmugavelandy, Todd Fox, Giuseppe Mazza, Josepmaria Argemi, Ramon Bataller, Lauren Ashley Cowart, Mark Kester, Massimo Pinzani, Krista Rombouts. Exogenous Liposomal Ceramide-C6 Ameliorates Lipidomic Profile, Energy Homeostasis, and Anti-Oxidant Systems in NASH. Cells. 2020 05; 9(5):. doi: 10.3390/cells9051237. [PMID: 32429478]
  • Jianzhong Chen, Sachin K Khiste, Xiaomei Fu, Kartik R Roy, Yixuan Dong, Jian Zhang, Mei Liu, Yong-Yu Liu, Zhijun Liu. Rubusoside-assisted solubilization of poorly soluble C6-Ceramide for a pilot pharmacokinetic study. Prostaglandins & other lipid mediators. 2020 02; 146(?):106402. doi: 10.1016/j.prostaglandins.2019.106402. [PMID: 31841664]
  • Lei Li, Mridula Dwivedi, Nelli Erwin, Simone Möbitz, Peter Nussbaumer, Roland Winter. Interaction of KRas4B protein with C6-ceramide containing lipid model membranes. Biochimica et biophysica acta. Biomembranes. 2018 May; 1860(5):1008-1014. doi: 10.1016/j.bbamem.2018.01.016. [PMID: 29357287]
  • Qian Cheng, Xin Li, Yue Wang, Min Dong, Feng-Huang Zhan, Jing Liu. The ceramide pathway is involved in the survival, apoptosis and exosome functions of human multiple myeloma cells in vitro. Acta pharmacologica Sinica. 2018 Apr; 39(4):561-568. doi: 10.1038/aps.2017.118. [PMID: 28858294]
  • Samy A F Morad, Terence E Ryan, P Darrell Neufer, Tonya N Zeczycki, Traci S Davis, Matthew R MacDougall, Todd E Fox, Su-Fern Tan, David J Feith, Thomas P Loughran, Mark Kester, David F Claxton, Brian M Barth, Tye G Deering, Myles C Cabot. Ceramide-tamoxifen regimen targets bioenergetic elements in acute myelogenous leukemia. Journal of lipid research. 2016 07; 57(7):1231-42. doi: 10.1194/jlr.m067389. [PMID: 27140664]
  • Srinivas Ganta, Amit Singh, Niravkumar R Patel, Joseph Cacaccio, Yashesh H Rawal, Barbara J Davis, Mansoor M Amiji, Timothy P Coleman. Development of EGFR-targeted nanoemulsion for imaging and novel platinum therapy of ovarian cancer. Pharmaceutical research. 2014 Sep; 31(9):2490-502. doi: 10.1007/s11095-014-1345-z. [PMID: 24643932]
  • Santosh S Dhule, Patrice Penfornis, Jibao He, Michael R Harris, Treniece Terry, Vijay John, Radhika Pochampally. The combined effect of encapsulating curcumin and C6 ceramide in liposomal nanoparticles against osteosarcoma. Molecular pharmaceutics. 2014 Feb; 11(2):417-27. doi: 10.1021/mp400366r. [PMID: 24380633]
  • Yongzhong Wang, Yunfei Ding, Ziming Liu, Xingrong Liu, Li Chen, Weili Yan. Bioactive lipids-based pH sensitive micelles for co-delivery of doxorubicin and ceramide to overcome multidrug resistance in leukemia. Pharmaceutical research. 2013 Nov; 30(11):2902-16. doi: 10.1007/s11095-013-1121-5. [PMID: 23793993]
  • Paul Dent. Ceramide in the prostate. Cancer biology & therapy. 2013 Oct; 14(10):881-2. doi: 10.4161/cbt.26212. [PMID: 24025252]
  • Archana Mukhopadhyay, Kayann Tabanor, Rathnam Chaguturu, Jane V Aldrich. Targeting inhibitor 2 of protein phosphatase 2A as a therapeutic strategy for prostate cancer treatment. Cancer biology & therapy. 2013 Oct; 14(10):962-72. doi: 10.4161/cbt.25943. [PMID: 24025258]
  • Chin Siang Kue, Hui Xuan Lim, Mi Young Jung, Hye-Jin Hong, Daeho Cho, Tae Sung Kim. C6-ceramide in combination with transforming growth factor-β enhances Treg cell differentiation and stable FoxP3 expression in vitro and in vivo. Immunobiology. 2013 Jul; 218(7):952-9. doi: 10.1016/j.imbio.2012.11.003. [PMID: 23313049]
  • Juan M Duran, Felix Campelo, Josse van Galen, Timo Sachsenheimer, Jesús Sot, Mikhail V Egorov, Carles Rentero, Carlos Enrich, Roman S Polishchuk, Félix M Goñi, Britta Brügger, Felix Wieland, Vivek Malhotra. Sphingomyelin organization is required for vesicle biogenesis at the Golgi complex. The EMBO journal. 2012 Dec; 31(24):4535-46. doi: 10.1038/emboj.2012.317. [PMID: 23178595]
  • Takayuki Sassa, Shota Suto, Yuriko Okayasu, Akio Kihara. A shift in sphingolipid composition from C24 to C16 increases susceptibility to apoptosis in HeLa cells. Biochimica et biophysica acta. 2012 Jul; 1821(7):1031-7. doi: 10.1016/j.bbalip.2012.04.008. [PMID: 22579584]
  • 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]
  • Margaret Flowers, Gemma Fabriás, Antonio Delgado, Josefina Casas, Jose Luis Abad, Myles C Cabot. C6-ceramide and targeted inhibition of acid ceramidase induce synergistic decreases in breast cancer cell growth. Breast cancer research and treatment. 2012 Jun; 133(2):447-58. doi: 10.1007/s10549-011-1768-8. [PMID: 21935601]
  • Jong Min Choi, So Jung Chu, Kyong Hoon Ahn, Seok Kyun Kim, Jung Eun Ji, Jong Hoon Won, Hyung Chul Kim, Moon Jung Back, Dae Kyong Kim. C(6)-ceramide enhances phagocytic activity of Kupffer cells through the production of endogenous ceramides. Molecules and cells. 2011 Oct; 32(4):325-31. doi: 10.1007/s10059-011-1034-2. [PMID: 21874540]
  • Javier Moral-Sanz, Teresa Gonzalez, Carmen Menendez, Miren David, Laura Moreno, Alvaro Macias, Julio Cortijo, Carmen Valenzuela, Francisco Perez-Vizcaino, Angel Cogolludo. Ceramide inhibits Kv currents and contributes to TP-receptor-induced vasoconstriction in rat and human pulmonary arteries. American journal of physiology. Cell physiology. 2011 Jul; 301(1):C186-94. doi: 10.1152/ajpcell.00243.2010. [PMID: 21490312]
  • Wing-Kee Lee, Blazej Torchalski, Naschla Kohistani, Frank Thévenod. ABCB1 protects kidney proximal tubule cells against cadmium-induced apoptosis: roles of cadmium and ceramide transport. Toxicological sciences : an official journal of the Society of Toxicology. 2011 Jun; 121(2):343-56. doi: 10.1093/toxsci/kfr071. [PMID: 21436125]
  • Qi Hou, Junfei Jin, Hui Zhou, Sergei A Novgorodov, Alicja Bielawska, Zdzislaw M Szulc, Yusuf A Hannun, Lina M Obeid, Yi-Te Hsu. Mitochondrially targeted ceramides preferentially promote autophagy, retard cell growth, and induce apoptosis. Journal of lipid research. 2011 Feb; 52(2):278-88. doi: 10.1194/jlr.m012161. [PMID: 21081756]
  • Benjamin Smith, Francesca Galbiati, Ludovico Cantuti Castelvetri, Maria I Givogri, Aurora Lopez-Rosas, Ernesto R Bongarzone. Peripheral neuropathy in the Twitcher mouse involves the activation of axonal caspase 3. ASN neuro. 2011; 3(4):. doi: 10.1042/an20110019. [PMID: 21929508]
  • Jeffrey D Clogston, Anil K Patri. Lipid component quantitation by thin layer chromatography. Methods in molecular biology (Clifton, N.J.). 2011; 697(?):109-17. doi: 10.1007/978-1-60327-198-1_11. [PMID: 21116959]
  • Zdzislaw M Szulc, Aiping Bai, Jacek Bielawski, Nalini Mayroo, Doreen E Miller, Hanna Gracz, Yusuf A Hannun, Alicja Bielawska. Synthesis, NMR characterization and divergent biological actions of 2'-hydroxy-ceramide/dihydroceramide stereoisomers in MCF7 cells. Bioorganic & medicinal chemistry. 2010 Nov; 18(21):7565-79. doi: 10.1016/j.bmc.2010.08.050. [PMID: 20851613]
  • Sindura B Ganapathi, Todd E Fox, Mark Kester, Keith S Elmslie. Ceramide modulates HERG potassium channel gating by translocation into lipid rafts. American journal of physiology. Cell physiology. 2010 Jul; 299(1):C74-86. doi: 10.1152/ajpcell.00462.2009. [PMID: 20375276]
  • Yong-Yu Liu, Jing Yuan Yu, Dongmei Yin, Gauri Anand Patwardhan, Vineet Gupta, Yoshio Hirabayashi, Walter M Holleran, Armando E Giuliano, S Michal Jazwinski, Valerie Gouaze-Andersson, David P Consoli, Myles C Cabot. A role for ceramide in driving cancer cell resistance to doxorubicin. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2008 Jul; 22(7):2541-51. doi: 10.1096/fj.07-092981. [PMID: 18245173]
  • Kyle D Kent, Elizabeth A Clubbs, W James Harper, Joshua A Bomser. Apoptotic effects of dietary and synthetic sphingolipids in androgen-independent (PC-3) prostate cancer cells. Lipids. 2008 Feb; 43(2):143-9. doi: 10.1007/s11745-007-3148-z. [PMID: 18188632]
  • Chun Chui Tsao, Alina Felicia Nica, Svitlana M Kurinna, Tilahun Jiffar, Marc Mumby, Peter P Ruvolo. Mitochondrial protein phosphatase 2A regulates cell death induced by simulated ischemia in kidney NRK-52E cells. Cell cycle (Georgetown, Tex.). 2007 Oct; 6(19):2377-85. doi: 10.4161/cc.6.19.4737. [PMID: 17700073]
  • Abbas Samadi. Ceramide-induced cell death in lens epithelial cells. Molecular vision. 2007 Sep; 13(?):1618-26. doi: ". [PMID: 17893663]
  • Ramasubbu N Mahalakshmi, Mei Yong Ng, Ke Guo, Zeng Qi, Walter Hunziker, Pascal Béguin. Nuclear localization of endogenous RGK proteins and modulation of cell shape remodeling by regulated nuclear transport. Traffic (Copenhagen, Denmark). 2007 Sep; 8(9):1164-78. doi: 10.1111/j.1600-0854.2007.00599.x. [PMID: 17605760]
  • Wing-Kee Lee, Blazej Torchalski, Frank Thévenod. Cadmium-induced ceramide formation triggers calpain-dependent apoptosis in cultured kidney proximal tubule cells. American journal of physiology. Cell physiology. 2007 Sep; 293(3):C839-47. doi: 10.1152/ajpcell.00197.2007. [PMID: 17596294]
  • Todd E Fox, Kristy L Houck, Sean M O'Neill, Murali Nagarajan, Thomas C Stover, Pawel T Pomianowski, Onur Unal, Jong K Yun, Stanley J Naides, Mark Kester. Ceramide recruits and activates protein kinase C zeta (PKC zeta) within structured membrane microdomains. The Journal of biological chemistry. 2007 Apr; 282(17):12450-7. doi: 10.1074/jbc.m700082200. [PMID: 17308302]
  • Leyre Brizuela, Miriam Rábano, Ana Peña, Patricia Gangoiti, José María Macarulla, Miguel Trueba, Antonio Gómez-Muñoz. Sphingosine 1-phosphate: a novel stimulator of aldosterone secretion. Journal of lipid research. 2006 Jun; 47(6):1238-49. doi: 10.1194/jlr.m500510-jlr200. [PMID: 16554657]
  • Jesús Sot, Félix M Goñi, Alicia Alonso. Molecular associations and surface-active properties of short- and long-N-acyl chain ceramides. Biochimica et biophysica acta. 2005 Jun; 1711(1):12-9. doi: 10.1016/j.bbamem.2005.02.014. [PMID: 15904658]
  • Thomas C Stover, Arati Sharma, Gavin P Robertson, Mark Kester. Systemic delivery of liposomal short-chain ceramide limits solid tumor growth in murine models of breast adenocarcinoma. Clinical cancer research : an official journal of the American Association for Cancer Research. 2005 May; 11(9):3465-74. doi: 10.1158/1078-0432.ccr-04-1770. [PMID: 15867249]
  • Karsten Lindner, Ulrike Uhlig, Stefan Uhlig. Ceramide alters endothelial cell permeability by a nonapoptotic mechanism. British journal of pharmacology. 2005 May; 145(1):132-40. doi: 10.1038/sj.bjp.0706173. [PMID: 15735657]
  • 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]
  • Elizabeth M Jablonski, Ashley N Webb, Nisha A McConnell, Marcus C Riley, Francis M Hughes. Plasma membrane aquaporin activity can affect the rate of apoptosis but is inhibited after apoptotic volume decrease. American journal of physiology. Cell physiology. 2004 Apr; 286(4):C975-85. doi: 10.1152/ajpcell.00180.2003. [PMID: 14644770]
  • Tom Stover, Mark Kester. Liposomal delivery enhances short-chain ceramide-induced apoptosis of breast cancer cells. The Journal of pharmacology and experimental therapeutics. 2003 Nov; 307(2):468-75. doi: 10.1124/jpet.103.054056. [PMID: 12975495]
  • Marianne Fillet, Mohamed Bentires-Alj, Valerie Deregowski, Roland Greimers, Jacques Gielen, Jacques Piette, Vincent Bours, Marie-Paule Merville. Mechanisms involved in exogenous C2- and C6-ceramide-induced cancer cell toxicity. Biochemical pharmacology. 2003 May; 65(10):1633-42. doi: 10.1016/s0006-2952(03)00125-4. [PMID: 12754099]
  • 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]
  • Pradeep Sathyanarayana, Manoj K Barthwal, Chanakya N Kundu, Mary Ellen Lane, Andreas Bergmann, Guri Tzivion, Ajay Rana. Activation of the Drosophila MLK by ceramide reveals TNF-alpha and ceramide as agonists of mammalian MLK3. Molecular cell. 2002 Dec; 10(6):1527-33. doi: 10.1016/s1097-2765(02)00734-7. [PMID: 12504027]
  • H J Kim, J Y Mun, Y J Chun, K H Choi, M Y Kim. Bax-dependent apoptosis induced by ceramide in HL-60 cells. FEBS letters. 2001 Sep; 505(2):264-8. doi: 10.1016/s0014-5793(01)02836-8. [PMID: 11566188]
  • B Ogretmen, D Schady, J Usta, R Wood, J M Kraveka, C Luberto, H Birbes, Y A Hannun, L M Obeid. Role of ceramide in mediating the inhibition of telomerase activity in A549 human lung adenocarcinoma cells. The Journal of biological chemistry. 2001 Jul; 276(27):24901-10. doi: 10.1074/jbc.m100314200. [PMID: 11335714]
  • Q He, R T Riley, R P Sharma. Fumonisin-induced tumor necrosis factor-alpha expression in a porcine kidney cell line is independent of sphingoid base accumulation induced by ceramide synthase inhibition. Toxicology and applied pharmacology. 2001 Jul; 174(1):69-77. doi: 10.1006/taap.2001.9189. [PMID: 11437650]
  • N A Bourbon, J Yun, D Berkey, Y Wang, M Kester. Inhibitory actions of ceramide upon PKC-epsilon/ERK interactions. American journal of physiology. Cell physiology. 2001 Jun; 280(6):C1403-11. doi: 10.1152/ajpcell.2001.280.6.c1403. [PMID: 11350735]
  • M Selzner, A Bielawska, M A Morse, H A Rüdiger, D Sindram, Y A Hannun, P A Clavien. Induction of apoptotic cell death and prevention of tumor growth by ceramide analogues in metastatic human colon cancer. Cancer research. 2001 Feb; 61(3):1233-40. doi: ". [PMID: 11221856]
  • S Jayadev, J C Barrett, E Murphy. Elevated ceramide is downstream of altered calcium homeostasis in low serum-induced apoptosis. American journal of physiology. Cell physiology. 2000 Nov; 279(5):C1640-7. doi: 10.1152/ajpcell.2000.279.5.c1640. [PMID: 11029312]
  • K Kitatani, T Oka, T Murata, M Hayama, S Akiba, T Sato. Acceleration by ceramide of calcium-dependent translocation of phospholipase A2 from cytosol to membranes in platelets. Archives of biochemistry and biophysics. 2000 Oct; 382(2):296-302. doi: 10.1006/abbi.2000.2028. [PMID: 11068881]
  • E Klapisz, J Masliah, G Béréziat, C Wolf, K S Koumanov. Sphingolipids and cholesterol modulate membrane susceptibility to cytosolic phospholipase A(2). Journal of lipid research. 2000 Oct; 41(10):1680-8. doi: 10.1016/s0022-2275(20)32002-2. [PMID: 11013311]
  • R Charles, L Sandirasegarane, J Yun, N Bourbon, R Wilson, R P Rothstein, S W Levison, M Kester. Ceramide-coated balloon catheters limit neointimal hyperplasia after stretch injury in carotid arteries. Circulation research. 2000 Aug; 87(4):282-8. doi: 10.1161/01.res.87.4.282. [PMID: 10948061]
  • K L Puranam, W X Guo, W H Qian, K Nikbakht, R M Boustany. CLN3 defines a novel antiapoptotic pathway operative in neurodegeneration and mediated by ceramide. Molecular genetics and metabolism. 1999 Apr; 66(4):294-308. doi: 10.1006/mgme.1999.2834. [PMID: 10191118]
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  • F Irie, Y Hirabayashi. Application of exogenous ceramide to cultured rat spinal motoneurons promotes survival or death by regulation of apoptosis depending on its concentrations. Journal of neuroscience research. 1998 Nov; 54(4):475-85. doi: 10.1002/(sici)1097-4547(19981115)54:4<475::aid-jnr5>3.0.co;2-p. [PMID: 9822158]
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  • J W Kok, T Babia, C M Filipeanu, A Nelemans, G Egea, D Hoekstra. PDMP blocks brefeldin A-induced retrograde membrane transport from golgi to ER: evidence for involvement of calcium homeostasis and dissociation from sphingolipid metabolism. The Journal of cell biology. 1998 Jul; 142(1):25-38. doi: 10.1083/jcb.142.1.25. [PMID: 9660860]
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  • S D Long, P H Pekala. Lipid mediators of insulin resistance: ceramide signalling down-regulates GLUT4 gene transcription in 3T3-L1 adipocytes. The Biochemical journal. 1996 Oct; 319 ( Pt 1)(?):179-84. doi: 10.1042/bj3190179. [PMID: 8870666]