HELSS (BioDeep_00000605576)

   


代谢物信息卡片


6E-(bromomethylene)tetrahydro-3-(1-naphthalenyl)-2H-pyran-2-one

化学式: C16H13BrO2 (316.0098858)
中文名称: 溴烯醇内酯
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CC(=CBr)OC(=O)C1C2=CC=CC3=CC=CC=C32
InChI: InChI=1S/C16H13BrO2/c17-10-12-8-9-15(16(18)19-12)14-7-3-5-11-4-1-2-6-13(11)14/h1-7,10,15H,8-9H2/b12-10+

描述信息

D004791 - Enzyme Inhibitors > D010726 - Phosphodiesterase Inhibitors
Bromoenol lactone ((6E)-Bromoenol lactone) is a suicide-based irreversible, selective, potent inhibitor of calcium-independent phospholipase A2 (iPLA2β) with an IC50 value of approximately 7 μM, which inhibits antigen-stimulated mast cell exocytosis without blocking Ca2+ influx[1][2].

同义名列表

4 个代谢物同义名

Bromoenol lactone; HELSS; 6E-(bromomethylene)tetrahydro-3-(1-naphthalenyl)-2H-pyran-2-one; (6E)-Bromoenol lactone



数据库引用编号

6 个数据库交叉引用编号

分类词条

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。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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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

  • Satoko Nakayama, Emiko Yoda, Saki Yamashita, Yuka Takamatsu, Yasutomo Suzuki, Yukihiro Kondo, Shuntaro Hara. Knockdown of iPLA2γ enhances cisplatin-induced apoptosis by increasing ROS-dependent peroxidation of mitochondrial phospholipids in bladder cancer cells. Free radical biology & medicine. 2024 Aug; 220(?):301-311. doi: 10.1016/j.freeradbiomed.2024.05.016. [PMID: 38734266]
  • Adam J Rauckhorst, Kimberly M Broekemeier, Douglas R Pfeiffer. Regulation of the Ca(2+)-independent phospholipase A2 in liver mitochondria by changes in the energetic state. Journal of lipid research. 2014 May; 55(5):826-36. doi: 10.1194/jlr.m043307. [PMID: 24586040]
  • Andre C Eaddy, Brian S Cummings, Jane McHowat, Rick G Schnellmann. The role of endoplasmic reticulum Ca2+-independent phospholipase a2γ in oxidant-induced lipid peroxidation, Ca2+ release, and renal cell death. Toxicological sciences : an official journal of the Society of Toxicology. 2012 Aug; 128(2):544-52. doi: 10.1093/toxsci/kfs175. [PMID: 22584685]
  • A Paliege, T Roeschel, H Neymeyer, S Seidel, T Kahl, A L Daigeler, K Mutig, R Mrowka, N R Ferreri, B S Wilson, N Himmerkus, M Bleich, S Bachmann. Group VIA phospholipase A2 is a target for vasopressin signaling in the thick ascending limb. American journal of physiology. Renal physiology. 2012 Apr; 302(7):F865-74. doi: 10.1152/ajprenal.00222.2011. [PMID: 22218592]
  • Haowei Song, Mary Wohltmann, Min Tan, Shunzhong Bao, Jack H Ladenson, John Turk. Group VIA PLA2 (iPLA2β) is activated upstream of p38 mitogen-activated protein kinase (MAPK) in pancreatic islet β-cell signaling. The Journal of biological chemistry. 2012 Feb; 287(8):5528-41. doi: 10.1074/jbc.m111.285114. [PMID: 22194610]
  • Saikat Chakraborty, Zachary C Berwick, Paula J Bartlett, Sanjay Kumar, Andrew P Thomas, Michael Sturek, Johnathan D Tune, Alexander G Obukhov. Bromoenol lactone inhibits voltage-gated Ca2+ and transient receptor potential canonical channels. The Journal of pharmacology and experimental therapeutics. 2011 Nov; 339(2):329-40. doi: 10.1124/jpet.111.183673. [PMID: 21795434]
  • Jason L Blum, Gilbert R Kinsey, Prashant Monian, Bin Sun, Brian S Cummings, Jane McHowat, Rick G Schnellmann. Profiling of fatty acids released during calcium-induced mitochondrial permeability transition in isolated rabbit kidney cortex mitochondria. Toxicology in vitro : an international journal published in association with BIBRA. 2011 Aug; 25(5):1001-6. doi: 10.1016/j.tiv.2011.03.014. [PMID: 21443943]
  • Myoung Sook Han, Yu-Mi Lim, Wenying Quan, Jung Ran Kim, Kun Wook Chung, Mira Kang, Sunshin Kim, Sun Young Park, Joong-Soo Han, Shin-Young Park, Hyae Gyeong Cheon, Sang Dal Rhee, Tae-Sik Park, Myung-Shik Lee. Lysophosphatidylcholine as an effector of fatty acid-induced insulin resistance. Journal of lipid research. 2011 Jun; 52(6):1234-1246. doi: 10.1194/jlr.m014787. [PMID: 21447485]
  • Vincenzo Lariccia, Michael Fine, Simona Magi, Mei-Jung Lin, Alp Yaradanakul, Marc C Llaguno, Donald W Hilgemann. Massive calcium-activated endocytosis without involvement of classical endocytic proteins. The Journal of general physiology. 2011 Jan; 137(1):111-32. doi: 10.1085/jgp.201010468. [PMID: 21187336]
  • Andreas Drews, Stefanie Bovens, Kirsten Roebrock, Cord Sunderkötter, Dirk Reinhardt, Michael Schäfers, Andrea van der Velde, Alwine Schulze Elfringhoff, Jörg Fabian, Matthias Lehr. 1-(5-carboxyindol-1-yl)propan-2-one inhibitors of human cytosolic phospholipase A(2)alpha with reduced lipophilicity: synthesis, biological activity, metabolic stability, solubility, bioavailability, and topical in vivo activity. Journal of medicinal chemistry. 2010 Jul; 53(14):5165-78. doi: 10.1021/jm1001088. [PMID: 20583844]
  • Mounia Beloueche-Babari, Vaitha Arunan, L Elizabeth Jackson, Nina Perusinghe, Swee Y Sharp, Paul Workman, Martin O Leach. Modulation of melanoma cell phospholipid metabolism in response to heat shock protein 90 inhibition. Oncotarget. 2010 Jul; 1(3):185-97. doi: 10.18632/oncotarget.125. [PMID: 21037799]
  • Andrej Grkovich, Aaron Armando, Oswald Quehenberger, Edward A Dennis. TLR-4 mediated group IVA phospholipase A(2) activation is phosphatidic acid phosphohydrolase 1 and protein kinase C dependent. Biochimica et biophysica acta. 2009 Oct; 1791(10):975-82. doi: 10.1016/j.bbalip.2009.02.002. [PMID: 19230851]
  • Thomas M Nicotera, David P Schuster, Mustapha Bourhim, Kailash Chadha, Gary Klaich, David A Corral. Regulation of PSA secretion and survival signaling by calcium-independent phopholipase A(2)beta in prostate cancer cells. The Prostate. 2009 Sep; 69(12):1270-80. doi: 10.1002/pros.20968. [PMID: 19475654]
  • Brianna Peterson, Kyndra Stovall, Prashant Monian, James L Franklin, Brian S Cummings. Alterations in phospholipid and fatty acid lipid profiles in primary neocortical cells during oxidant-induced cell injury. Chemico-biological interactions. 2008 Aug; 174(3):163-76. doi: 10.1016/j.cbi.2008.05.028. [PMID: 18602625]
  • Tarik Smani, Tina Patel, Victoria M Bolotina. Complex regulation of store-operated Ca2+ entry pathway by PKC-epsilon in vascular SMCs. American journal of physiology. Cell physiology. 2008 Jun; 294(6):C1499-508. doi: 10.1152/ajpcell.00365.2007. [PMID: 18434622]
  • K Ross, G Parker, M Whitaker, N J Reynolds. Inhibition of calcium-independent phospholipase A impairs agonist-induced calcium entry in keratinocytes. The British journal of dermatology. 2008 Jan; 158(1):31-7. doi: 10.1111/j.1365-2133.2007.08298.x. [PMID: 18028502]
  • Jessica N Mazerik, Thomas Hagele, Shariq Sherwani, Valorie Ciapala, Susan Butler, M Lakshmi Kuppusamy, Melissa Hunter, Periannan Kuppusamy, Clay B Marsh, Narasimham L Parinandi. Phospholipase A2 activation regulates cytotoxicity of methylmercury in vascular endothelial cells. International journal of toxicology. 2007 Nov; 26(6):553-69. doi: 10.1080/10915810701707759. [PMID: 18066971]
  • Salam Ibrahim, Catherine Calzada, Valérie Pruneta-Deloche, Michel Lagarde, Gabriel Ponsin. The transfer of VLDL-associated phospholipids to activated platelets depends upon cytosolic phospholipase A2 activity. Journal of lipid research. 2007 Jul; 48(7):1533-8. doi: 10.1194/jlr.m600480-jlr200. [PMID: 17456899]
  • Kehinde Ross, Michael Whitaker, Nick J Reynolds. Agonist-induced calcium entry correlates with STIM1 translocation. Journal of cellular physiology. 2007 Jun; 211(3):569-76. doi: 10.1002/jcp.20993. [PMID: 17299780]
  • Gilbert R Kinsey, Jane McHowat, Kennerly S Patrick, Rick G Schnellmann. Role of Ca2+-independent phospholipase A2gamma in Ca2+-induced mitochondrial permeability transition. The Journal of pharmacology and experimental therapeutics. 2007 May; 321(2):707-15. doi: 10.1124/jpet.107.119545. [PMID: 17312185]
  • Gilbert R Kinsey, Jane McHowat, Caroline S Beckett, Rick G Schnellmann. Identification of calcium-independent phospholipase A2gamma in mitochondria and its role in mitochondrial oxidative stress. American journal of physiology. Renal physiology. 2007 Feb; 292(2):F853-60. doi: 10.1152/ajprenal.00318.2006. [PMID: 17047165]
  • Edward A Lock, Celia J Reed, Gilbert R Kinsey, Rick G Schnellmann. Caspase-dependent and -independent induction of phosphatidylserine externalization during apoptosis in human renal carcinoma Cak(1)-1 and A-498 cells. Toxicology. 2007 Jan; 229(1-2):79-90. doi: 10.1016/j.tox.2006.10.003. [PMID: 17097791]
  • François-Xavier Boittin, Olivier Petermann, Carole Hirn, Peggy Mittaud, Olivier M Dorchies, Emmanuelle Roulet, Urs T Ruegg. Ca2+-independent phospholipase A2 enhances store-operated Ca2+ entry in dystrophic skeletal muscle fibers. Journal of cell science. 2006 Sep; 119(Pt 18):3733-42. doi: 10.1242/jcs.03184. [PMID: 16926189]
  • Juan Ren, Yi-jin Xiao, Lisam Shanjukumar Singh, Xiaoxian Zhao, Zhenwen Zhao, Li Feng, Tyler M Rose, Glenn D Prestwich, Yan Xu. Lysophosphatidic acid is constitutively produced by human peritoneal mesothelial cells and enhances adhesion, migration, and invasion of ovarian cancer cells. Cancer research. 2006 Mar; 66(6):3006-14. doi: 10.1158/0008-5472.can-05-1292. [PMID: 16540649]
  • Haowei Song, Sasanka Ramanadham, Shunzhong Bao, Fong-Fu Hsu, John Turk. A bromoenol lactone suicide substrate inactivates group VIA phospholipase A2 by generating a diffusible bromomethyl keto acid that alkylates cysteine thiols. Biochemistry. 2006 Jan; 45(3):1061-73. doi: 10.1021/bi052065q. [PMID: 16411783]
  • Oliver Wichmann, Jochen Wittbrodt, Carsten Schultz. A small-molecule FRET probe to monitor phospholipase A2 activity in cells and organisms. Angewandte Chemie (International ed. in English). 2006 Jan; 45(3):508-12. doi: 10.1002/anie.200500751. [PMID: 16323228]
  • Evelin L Schaeffer, Wagner F Gattaz. Inhibition of calcium-independent phospholipase A2 activity in rat hippocampus impairs acquisition of short- and long-term memory. Psychopharmacology. 2005 Sep; 181(2):392-400. doi: 10.1007/s00213-005-2256-9. [PMID: 15830227]
  • Christine Péchoux, Raphaël Boisgard, Eric Chanat, Françoise Lavialle. Ca(2+)-independent phospholipase A2 participates in the vesicular transport of milk proteins. Biochimica et biophysica acta. 2005 Apr; 1743(3):317-29. doi: 10.1016/j.bbamcr.2005.01.006. [PMID: 15843044]
  • Gilbert R Kinsey, Brian S Cummings, Caroline S Beckett, Geraldine Saavedra, Wenliang Zhang, Jane McHowat, Rick G Schnellmann. Identification and distribution of endoplasmic reticulum iPLA2. Biochemical and biophysical research communications. 2005 Feb; 327(1):287-93. doi: 10.1016/j.bbrc.2004.12.016. [PMID: 15629460]
  • Michael N P Ng, Theresa E Kitos, Rosemary B Cornell. Contribution of lipid second messengers to the regulation of phosphatidylcholine synthesis during cell cycle re-entry. Biochimica et biophysica acta. 2004 Nov; 1686(1-2):85-99. doi: 10.1016/j.bbalip.2004.09.001. [PMID: 15522825]
  • Yi Liu, Yi Zhu, Francois Rannou, Tzong-Shyuan Lee, Kitty Formentin, Lingfang Zeng, Xiaohui Yuan, Nanping Wang, Shu Chien, Barry M Forman, John Y-J Shyy. Laminar flow activates peroxisome proliferator-activated receptor-gamma in vascular endothelial cells. Circulation. 2004 Aug; 110(9):1128-33. doi: 10.1161/01.cir.0000139850.08365.ec. [PMID: 15313948]
  • Brian S Cummings, Andrew K Gelasco, Gilbert R Kinsey, Jane McHowat, Rick G Schnellmann. Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress. Journal of the American Society of Nephrology : JASN. 2004 Jun; 15(6):1441-51. doi: 10.1097/01.asn.0000127923.57438.ec. [PMID: 15153555]
  • Jay S Grider, Cobern E Ott, Brian A Jackson. Dopamine D1 receptor-dependent inhibition of NaCl transport in the rat thick ascending limb: mechanism of action. European journal of pharmacology. 2003 Jul; 473(2-3):185-90. doi: 10.1016/s0014-2999(03)01965-4. [PMID: 12892837]
  • Brian S Cummings, Jane McHowat, Rick G Schnellmann. Role of an endoplasmic reticulum Ca(2+)-independent phospholipase A(2) in oxidant-induced renal cell death. American journal of physiology. Renal physiology. 2002 Sep; 283(3):F492-8. doi: 10.1152/ajprenal.00022.2002. [PMID: 12167600]
  • Syed Jalal Khundmiri, Eleanor Lederer. PTH and DA regulate Na-K ATPase through divergent pathways. American journal of physiology. Renal physiology. 2002 Mar; 282(3):F512-22. doi: 10.1152/ajprenal.00111.2000. [PMID: 11832434]
  • J McHowat, P J Kell, H B O'Neill, M H Creer. Endothelial cell PAF synthesis following thrombin stimulation utilizes Ca(2+)-independent phospholipase A(2). Biochemistry. 2001 Dec; 40(49):14921-31. doi: 10.1021/bi0156153. [PMID: 11732912]
  • L N Berti-Mattera, S Harwalkar, B Hughes, P L Wilkins, K Almhanna. Proliferative and morphological effects of endothelins in Schwann cells: roles of p38 mitogen-activated protein kinase and Ca(2+)-independent phospholipase A2. Journal of neurochemistry. 2001 Dec; 79(6):1136-48. doi: 10.1046/j.1471-4159.2001.00642.x. [PMID: 11752055]
  • M E Handlogten, C Huang, N Shiraishi, H Awata, R T Miller. The Ca2+-sensing receptor activates cytosolic phospholipase A2 via a Gqalpha -dependent ERK-independent pathway. The Journal of biological chemistry. 2001 Apr; 276(17):13941-8. doi: 10.1074/jbc.m007306200. [PMID: 11278341]
  • J McHowat, L M Swift, N Sarvazyan. Oxidant-induced inhibition of myocardial calcium-independent phospholipase A2. Cardiovascular toxicology. 2001; 1(4):309-16. doi: 10.1385/ct:1:4:309. [PMID: 12213969]
  • A K Roshak, E A Capper, C Stevenson, C Eichman, L A Marshall. Human calcium-independent phospholipase A2 mediates lymphocyte proliferation. The Journal of biological chemistry. 2000 Nov; 275(46):35692-8. doi: 10.1074/jbc.m002273200. [PMID: 10964913]
  • D E Yarger, C B Patrick, S I Rapoport, E J Murphy. A continuous fluorometric assay for phospholipase A(2) activity in brain cytosol. Journal of neuroscience methods. 2000 Jul; 100(1-2):127-33. doi: 10.1016/s0165-0270(00)00244-2. [PMID: 11040375]
  • C Pagès, A Rey, M Lafontan, P Valet, J S Saulnier-Blache. Ca(2+)-independent phospholipase A2 is required for alpha2-adrenergic-induced preadipocyte spreading. Biochemical and biophysical research communications. 1999 Nov; 265(2):572-6. doi: 10.1006/bbrc.1999.1726. [PMID: 10558911]
  • K Zabłocki, J Duszyński. Role of calcium-independent phospholipase A2 in the regulation of calcium influx into Jurkat cells. Polish journal of pharmacology. 1999 Mar; 51(2):163-6. doi: NULL. [PMID: 10425645]
  • J Balsinde, M A Balboa, E A Dennis. Antisense inhibition of group VI Ca2+-independent phospholipase A2 blocks phospholipid fatty acid remodeling in murine P388D1 macrophages. The Journal of biological chemistry. 1997 Nov; 272(46):29317-21. doi: 10.1074/jbc.272.46.29317. [PMID: 9361012]
  • M R Lennartz, A F Yuen, S M Masi, D G Russell, K F Buttle, J J Smith. Phospholipase A2 inhibition results in sequestration of plasma membrane into electronlucent vesicles during IgG-mediated phagocytosis. Journal of cell science. 1997 Sep; 110 ( Pt 17)(?):2041-52. doi: 10.1242/jcs.110.17.2041. [PMID: 9378755]
  • R W Gross, A E Rudolph, J Wang, C D Sommers, M J Wolf. Nitric oxide activates the glucose-dependent mobilization of arachidonic acid in a macrophage-like cell line (RAW 264.7) that is largely mediated by calcium-independent phospholipase A2. The Journal of biological chemistry. 1995 Jun; 270(25):14855-8. doi: 10.1074/jbc.270.25.14855. [PMID: 7797462]
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