N-(1,3-Dihydroxyoctadec-4-en-2-yl)acetamide (BioDeep_00000175550)
human metabolite blood metabolite
代谢物信息卡片
N-(1,3-Dihydroxyoctadec-4-en-2-yl)acetamide
化学式: C20H39NO3 (341.29297840000004)
中文名称:
谱图信息:
最多检出来源 Bos taurus(endogenous) 9.09%
分子结构信息
SMILES: CCCCCCCCCCCCCC=CC(O)C(CO)NC(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)
相关代谢途径
Reactome(0)
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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)
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
- 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.
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American journal of physiology. Endocrinology and metabolism.
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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.
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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.
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Cell death and differentiation.
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PloS one.
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Journal of lipids.
2011; 2011(?):565316. doi:
10.1155/2011/565316. [PMID: 21490804] - Chia-Yang Lu, Chien-Chun Li, Kai-Li Liu, Chia-Wen Tsai, Chong-Kuei Lii, Haw-Wen Chen. Docosahexaenoic acid down-regulates phenobarbital-induced cytochrome P450 2B1 gene expression in rat primary hepatocytes via the sphingomyelinase/ceramide pathway.
The Journal of nutritional biochemistry.
2010 Apr; 21(4):338-44. doi:
10.1016/j.jnutbio.2009.01.007. [PMID: 19427778] - Frank J Raucci, Dayanjan S Wijesinghe, Charles E Chalfant, Clive M Baumgarten. Exogenous and endogenous ceramides elicit volume-sensitive chloride current in ventricular myocytes.
Cardiovascular research.
2010 Apr; 86(1):55-62. doi:
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Lipids in health and disease.
2010 Feb; 9(?):15. doi:
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Cell cycle (Georgetown, Tex.).
2009 Nov; 8(22):3723-8. doi:
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The Journal of biological chemistry.
2009 Feb; 284(9):5697-708. 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:
10.1194/jlr.m600380-jlr200. [PMID: 16990644] - V E MacRae, T Burdon, S F Ahmed, C Farquharson. Ceramide inhibition of chondrocyte proliferation and bone growth is IGF-I independent.
The Journal of endocrinology.
2006 Nov; 191(2):369-77. doi:
10.1677/joe.1.06958. [PMID: 17088406] - Akira Abe, Miki Hiraoka, James A Shayman. Positional specificity of lysosomal phospholipase A2.
Journal of lipid research.
2006 Oct; 47(10):2268-79. doi:
10.1194/jlr.m600183-jlr200. [PMID: 16837646] - 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:
10.1002/ijc.21788. [PMID: 16432837] - 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] - 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:
10.1194/jlr.m500337-jlr200. [PMID: 16106045] - 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] - 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] - 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] - Helen E Townley, Kerrie McDonald, Gareth I Jenkins, Marc R Knight, Christopher J Leaver. Ceramides induce programmed cell death in Arabidopsis cells in a calcium-dependent manner.
Biological chemistry.
2005 Feb; 386(2):161-6. doi:
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Kidney international.
2004 Nov; 66(5):1890-900. doi:
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The Plant journal : for cell and molecular biology.
2004 Nov; 40(4):596-610. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
2004 Oct; 101(41):14788-93. doi:
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The Journal of veterinary medical science.
2004 Oct; 66(10):1177-82. doi:
10.1292/jvms.66.1177. [PMID: 15528845] - 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] - 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:
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Biochemical pharmacology.
2003 Dec; 66(11):2223-39. doi:
10.1016/j.bcp.2003.07.010. [PMID: 14609747] - 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:
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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] - 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] - Eduardo Latorre, M Pilar Collado, Inmaculada Fernández, M Dolores Aragonés, R Edgardo Catalán. Signaling events mediating activation of brain ethanolamine plasmalogen hydrolysis by ceramide.
European journal of biochemistry.
2003 Jan; 270(1):36-46. doi:
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Clinical cancer research : an official journal of the American Association for Cancer Research.
2003 Jan; 9(1):415-23. doi:
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Annals of the New York Academy of Sciences.
2002 Nov; 976(?):214-23. doi:
10.1111/j.1749-6632.2002.tb04744.x. [PMID: 12502564] - Teresa Gómez Del Pulgar, Maria L De Ceballos, Manuel Guzmán, Guillermo Velasco. Cannabinoids protect astrocytes from ceramide-induced apoptosis through the phosphatidylinositol 3-kinase/protein kinase B pathway.
The Journal of biological chemistry.
2002 Sep; 277(39):36527-33. doi:
10.1074/jbc.m205797200. [PMID: 12133838] - Monika Poppe, Claus Reimertz, Gudrun Münstermann, Donat Kögel, Jochen H M Prehn. Ceramide-induced apoptosis of D283 medulloblastoma cells requires mitochondrial respiratory chain activity but occurs independently of caspases and is not sensitive to Bcl-xL overexpression.
Journal of neurochemistry.
2002 Aug; 82(3):482-94. doi:
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The Journal of biological chemistry.
2002 Jul; 277(30):26796-803. doi:
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The Journal of laboratory and clinical medicine.
2002 Jul; 140(1):9-16. doi:
10.1067/mlc.2002.124551. [PMID: 12080323] - Shampa Mallick, Samir Kumar Mandal, Ranjan Bhadra. Human placental lipid induces mitogenesis and melanogenesis in B16F10 melanoma cells.
Journal of biosciences.
2002 Jun; 27(3):243-9. doi:
10.1007/bf02704913. [PMID: 12089473] - T Kondo, T Kitano, K Iwai, M Watanabe, Y Taguchi, T Yabu, H Umehara, N Domae, T Uchiyama, T Okazaki. Control of ceramide-induced apoptosis by IGF-1: involvement of PI-3 kinase, caspase-3 and catalase.
Cell death and differentiation.
2002 Jun; 9(6):682-92. doi:
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Journal of neuroscience research.
2002 May; 68(3):323-30. doi:
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The Journal of biological chemistry.
2002 Apr; 277(14):11788-94. doi:
10.1074/jbc.m111568200. [PMID: 11796726] - 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:
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The Journal of biological chemistry.
2002 Mar; 277(12):10100-7. doi:
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Experimental hematology.
2002 Mar; 30(3):272-8. doi:
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Molecular pharmacology.
2002 Mar; 61(3):620-7. doi:
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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:
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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.
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The British journal of dermatology.
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