N-Hexanoylsphingosine (BioDeep_00000176926)
human metabolite blood metabolite
代谢物信息卡片
N-(1,3-dihydroxyoctadec-4-en-2-yl)hexanamide
化学式: C24H47NO3 (397.3555752)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCCCCCCCCCC=CC(O)C(CO)NC(=O)CCCCC
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)
相关代谢途径
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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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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
- 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] - 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] - 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] - 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] - Lide Arana, Patricia Gangoiti, Alberto Ouro, Miguel Trueba, Antonio Gómez-Muñoz. Ceramide and ceramide 1-phosphate in health and disease.
Lipids in health and disease.
2010 Feb; 9(?):15. doi:
10.1186/1476-511x-9-15. [PMID: 20137073] - 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] - 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] - 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] - Malgorzata Czarny, Jan E Schnitzer. Neutral sphingomyelinase inhibitor scyphostatin prevents and ceramide mimics mechanotransduction in vascular endothelium.
American journal of physiology. Heart and circulatory physiology.
2004 Sep; 287(3):H1344-52. doi:
10.1152/ajpheart.00222.2004. [PMID: 15142848] - 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]