C2 Ceramide (BioDeep_00000598269)
代谢物信息卡片
N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-acetamide
化学式: C20H39NO3 (341.29297840000004)
中文名称: N-乙酰基神经鞘氨醇
谱图信息:
最多检出来源 Homo sapiens(lipidomics) 66.67%
分子结构信息
SMILES: C(/[C@H]([C@H](CO)NC(=O)C)O)=C\CCCCCCCCCCCCC
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+/m0/s1
描述信息
C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C61074 - Serine/Threonine Kinase Inhibitor
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors
A N-acylsphingosine that has an acetamido group at position 2.
D004791 - Enzyme Inhibitors
C2 Ceramide (Ceramide 2) is the main lipid of the stratum corneum and a protein phosphatase 1 (PP1) activator. C2 Ceramide activates PP2A and ceramide-activated protein phosphatase (CAPP). C2 Ceramide induces cells differentiation, autophagy and apoptosis, inhibits mitochondrial respiratory chain complex III. C2 Ceramide is also a skin conditioning agent that protects the epidermal barrier from water loss[1][2][3][4][5].
同义名列表
数据库引用编号
10 个数据库交叉引用编号
- ChEBI: CHEBI:46979
- ChEBI: CHEBI:92736
- PubChem: 5497136
- Metlin: METLIN411
- ChEMBL: CHEMBL105867
- LipidMAPS: LMSP02010014
- CAS: 195194-58-2
- CAS: 3102-57-6
- MetaboLights: MTBLC46979
- medchemexpress: HY-101180
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
- Tayde Quiroz-Acosta, Karina Bermeo, Isabel Arenas, David E Garcia. Inactivation of potassium channels by ceramide in rat pancreatic β-cells.
Archives of biochemistry and biophysics.
2023 02; 735(?):109520. doi:
10.1016/j.abb.2023.109520. [PMID: 36646267] - Yuanyuan Zhang, Bingke Ma, Shuangshuang Hao, Jiaqi Wang, Ruichen Zhang, Muhammad Ishfaq, Chenxi Shi, Liang Yuan, Rui Li, Changwen Li, Fangping Liu. Drug-induced liver injury: Oltipraz and C2-ceramide intervene HNF-1α/GSTA1 expression via JNK signaling pathway.
Journal of applied toxicology : JAT.
2021 12; 41(12):2011-2020. doi:
10.1002/jat.4181. [PMID: 33959992] - Akira Abe, Miki Hiraoka, Fumiko Matsuzawa, Sei-Ichi Aikawa, Youichi Niimura. Esterification of side-chain oxysterols by lysosomal phospholipase A2.
Biochimica et biophysica acta. Molecular and cell biology of lipids.
2020 10; 1865(10):158787. doi:
10.1016/j.bbalip.2020.158787. [PMID: 32777483] - 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] - Akira Abe, Miki Hiraoka, Hiroshi Ohguro, John J Tesmer, James A Shayman. Preferential hydrolysis of truncated oxidized glycerophospholipids by lysosomal phospholipase A2.
Journal of lipid research.
2017 02; 58(2):339-349. doi:
10.1194/jlr.m070730. [PMID: 27993948] - Yong Wang, Xingwen Li, Liyuan Sun, Baihuan Feng, Wenjun Sun. Acid sphingomyelinase mediates 50-Hz magnetic field-induced EGF receptor clustering on lipid raft.
Journal of receptor and signal transduction research.
2016 Dec; 36(6):593-600. doi:
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Theriogenology.
2013 Aug; 80(3):206-11. doi:
10.1016/j.theriogenology.2013.04.016. [PMID: 23731666] - 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:
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The Journal of biological chemistry.
2013 Jun; 288(24):17520-31. doi:
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PloS one.
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The Journal of biological chemistry.
2012 Nov; 287(47):39898-910. doi:
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The Journal of nutritional biochemistry.
2010 Apr; 21(4):338-44. doi:
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Cardiovascular research.
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Cell cycle (Georgetown, Tex.).
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The Journal of biological chemistry.
2009 Feb; 284(9):5697-708. doi:
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Blood.
2008 Apr; 111(8):4365-74. doi:
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Journal of lipid research.
2007 Oct; 48(10):2255-63. doi:
10.1194/jlr.m700277-jlr200. [PMID: 17626977] - Abbas Samadi. Ceramide-induced cell death in lens epithelial cells.
Molecular vision.
2007 Sep; 13(?):1618-26. doi:
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The European journal of neuroscience.
2007 May; 25(10):3030-8. doi:
10.1111/j.1460-9568.2007.05557.x. [PMID: 17561816] - Helena Van Overloop, Yves Denizot, Myriam Baes, Paul P Van Veldhoven. On the presence of C2-ceramide in mammalian tissues: possible relationship to etherphospholipids and phosphorylation by ceramide kinase.
Biological chemistry.
2007 Mar; 388(3):315-24. doi:
10.1515/bc.2007.035. [PMID: 17338639] - 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] - Amy B Ghering, W Sean Davidson. Ceramide structural features required to stimulate ABCA1-mediated cholesterol efflux to apolipoprotein A-I.
Journal of lipid research.
2006 Dec; 47(12):2781-8. doi:
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The Journal of endocrinology.
2006 Nov; 191(2):369-77. doi:
10.1677/joe.1.06958. [PMID: 17088406] - Bernhard Kniep, Eva Kniep, Nurdan Ozkucur, Steffen Barz, Michael Bachmann, Florence Malisan, Roberto Testi, Ernst Peter Rieber. 9-O-acetyl GD3 protects tumor cells from apoptosis.
International journal of cancer.
2006 Jul; 119(1):67-73. doi:
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Cellular signalling.
2006 Mar; 18(3):294-306. doi:
10.1016/j.cellsig.2005.05.012. [PMID: 16099142] - Natalia V Giltiay, Alexander A Karakashian, Alexander P Alimov, Sandy Ligthle, Mariana N Nikolova-Karakashian. Ceramide- and ERK-dependent pathway for the activation of CCAAT/enhancer binding protein by interleukin-1beta in hepatocytes.
Journal of lipid research.
2005 Nov; 46(11):2497-505. doi:
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2005 Aug; 81(4):541-50. doi:
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Biochimica et biophysica acta.
2005 Jun; 1711(1):12-9. doi:
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2005 Feb; 386(2):161-6. doi:
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The Journal of veterinary medical science.
2004 Oct; 66(10):1177-82. doi:
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Blood.
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Human reproduction (Oxford, England).
2003 Dec; 18(12):2672-7. doi:
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The Journal of biological chemistry.
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The Journal of biological chemistry.
2002 Mar; 277(12):10100-7. doi:
10.1074/jbc.m110321200. [PMID: 11792699] - 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] - Tadakazu Kondo, Yoshiko Suzuki, Toshiyuki Kitano, Kazuya Iwai, Mitsumasa Watanabe, Hisanori Umehara, Naoharu Daido, Naochika Domae, Masaro Tashima, Takashi Uchiyama, Toshiro Okazaki. Vesnarinone causes oxidative damage by inhibiting catalase function through ceramide action in myeloid cell apoptosis.
Molecular pharmacology.
2002 Mar; 61(3):620-7. doi:
10.1124/mol.61.3.620. [PMID: 11854443] - 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] - A Guidarelli, E Clementi, C De Nadai, R Bersacchi, O Cantoni. TNFalpha enhances the DNA single-strand breakage induced by the short-chain lipid hydroperoxide analogue tert-butylhydroperoxide via ceramide-dependent inhibition of complex III followed by enforced superoxide and hydrogen peroxide formation.
Experimental cell research.
2001 Oct; 270(1):56-65. doi:
10.1006/excr.2001.5323. [PMID: 11597127] - I N Singh, L M Stromberg, S G Bourgoin, V A Sciorra, A J Morris, D N Brindley. Ceramide inhibition of mammalian phospholipase D1 and D2 activities is antagonized by phosphatidylinositol 4,5-bisphosphate.
Biochemistry.
2001 Sep; 40(37):11227-33. doi:
10.1021/bi010787l. [PMID: 11551222] - G Ghosh Choudhury, J H Zhang, N Ghosh-Choudhury, H E Abboud. Ceramide blocks PDGF-induced DNA synthesis in mesangial cells via inhibition of Akt kinase in the absence of apoptosis.
Biochemical and biophysical research communications.
2001 Sep; 286(5):1183-90. doi:
10.1006/bbrc.2001.5483. [PMID: 11527425] - N Gupta, E Nodzenski, N N Khodarev, J Yu, L Khorasani, M A Beckett, D W Kufe, R R Weichselbaum. Angiostatin effects on endothelial cells mediated by ceramide and RhoA.
EMBO reports.
2001 Jun; 2(6):536-40. doi:
10.1093/embo-reports/kve115. [PMID: 11415988] - 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] - I Spyridopoulos, P Mayer, K S Shook, D I Axel, R Viebahn, K R Karsch. Loss of cyclin A and G1-cell cycle arrest are a prerequisite of ceramide-induced toxicity in human arterial endothelial cells.
Cardiovascular research.
2001 Apr; 50(1):97-107. doi:
10.1016/s0008-6363(01)00196-1. [PMID: 11282082] - 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] - S Stratford, D B DeWald, S A Summers. Ceramide dissociates 3'-phosphoinositide production from pleckstrin homology domain translocation.
The Biochemical journal.
2001 Mar; 354(Pt 2):359-68. doi:
10.1042/0264-6021:3540359. [PMID: 11171115] - 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 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] - 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] - 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] - 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] - C Paolucci, P Rovere, C De Nadai, A A Manfredi, E Clementi. Nitric oxide inhibits the tumor necrosis factor alpha -regulated endocytosis of human dendritic cells in a cyclic GMP-dependent way.
The Journal of biological chemistry.
2000 Jun; 275(26):19638-44. doi:
10.1074/jbc.m000511200. [PMID: 10777484] - 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] - G Dawson. Mechanisms of apoptosis in embryonic cortical neurons (E6 and E7) in culture involve lipid signalling, protein phosphorylation and caspase activation.
International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience.
2000 Apr; 18(2-3):247-57. doi:
10.1016/s0736-5748(99)00093-3. [PMID: 10715579] - D Lobner. Comparison of the LDH and MTT assays for quantifying cell death: validity for neuronal apoptosis?.
Journal of neuroscience methods.
2000 Mar; 96(2):147-52. doi:
10.1016/s0165-0270(99)00193-4. [PMID: 10720679] - K Migita, S Honda, S Yamasaki, Y Hirai, T Fukuda, T Aoyagi, M Kita, H Ida, T Tsukada, A Kawakami, Y Kawabe, K Eguchi. Regulation of rheumatoid synovial cell growth by ceramide.
Biochemical and biophysical research communications.
2000 Mar; 269(1):70-5. doi:
10.1006/bbrc.2000.2239. [PMID: 10694479] - 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] - D Allan. Lipid metabolic changes caused by short-chain ceramides and the connection with apoptosis.
The Biochemical journal.
2000 Feb; 345 Pt 3(?):603-10. doi:
10.1042/bj3450603. [PMID: 10642519] - M Sabatini, G Rolland, S Léonce, M Thomas, C Lesur, V Pérez, G de Nanteuil, J Bonnet. Effects of ceramide on apoptosis, proteoglycan degradation, and matrix metalloproteinase expression in rabbit articular cartilage.
Biochemical and biophysical research communications.
2000 Jan; 267(1):438-44. doi:
10.1006/bbrc.1999.1983. [PMID: 10623638]