N-[(2-chlorophenyl)methyl]-1-[4-[[(2-chlorophenyl)methylamino]methyl]cyclohexyl]methanamine (BioDeep_00000840697)

   


代谢物信息卡片


N-[(2-chlorophenyl)methyl]-1-[4-[[(2-chlorophenyl)methylamino]methyl]cyclohexyl]methanamine

化学式: C22H28Cl2N2 (390.1629428)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CC(CCC1CNCC2=CC=CC=C2Cl)CNCC3=CC=CC=C3Cl
InChI: InChI=1S/C22H28Cl2N2/c23-21-7-3-1-5-19(21)15-25-13-17-9-11-18(12-10-17)14-26-16-20-6-2-4-8-22(20)24/h1-8,17-18,25-26H,9-16H2

描述信息

D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents
D009676 - Noxae > D000963 - Antimetabolites
D004791 - Enzyme Inhibitors

同义名列表

1 个代谢物同义名

N-[(2-chlorophenyl)methyl]-1-[4-[[(2-chlorophenyl)methylamino]methyl]cyclohexyl]methanamine



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

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

  • Leila Gholami, Safura Jokar, Yousef Fatahi, Hedayat Samandari, Javad Hamzehalipour Almaki, Marjan Hosseini, Mohsen Parviz. Targeting Caveolin-1 and Claudin-5 with AY9944, Improve Blood-Brain Barrier Permeability; Computational Simulation and Experimental Study. Cellular and molecular neurobiology. 2022 May; 42(4):1125-1139. doi: 10.1007/s10571-020-01004-z. [PMID: 33222099]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Alireza P Shabanzadeh, Jason Charish, Nardos G Tassew, Nahal Farhani, Jinzhou Feng, Xinjue Qin, Shuzo Sugita, Andrea J Mothe, Thomas Wälchli, Paulo D Koeberle, Philippe P Monnier. Cholesterol synthesis inhibition promotes axonal regeneration in the injured central nervous system. Neurobiology of disease. 2021 03; 150(?):105259. doi: 10.1016/j.nbd.2021.105259. [PMID: 33434618]
  • Martin F J Perescis, Gilles van Luijtelaar, Clementina M van Rijn. Neonatal exposure to AY-9944 increases typical spike and wave discharges in WAG/Rij and Wistar rats. Epilepsy research. 2019 11; 157(?):106184. doi: 10.1016/j.eplepsyres.2019.106184. [PMID: 31539657]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Rebecca J Kapphahn, Michael J Richards, Deborah A Ferrington, Steven J Fliesler. Lipid-derived and other oxidative modifications of retinal proteins in a rat model of Smith-Lemli-Opitz syndrome. Experimental eye research. 2019 01; 178(?):247-254. doi: 10.1016/j.exer.2018.08.006. [PMID: 30114413]
  • Steven J Fliesler, Libin Xu. Oxysterols and Retinal Degeneration in a Rat Model of Smith-Lemli-Opitz Syndrome: Implications for an Improved Therapeutic Intervention. Molecules (Basel, Switzerland). 2018 Oct; 23(10):. doi: 10.3390/molecules23102720. [PMID: 30360379]
  • Leonardo Gatticchi, Bruno Cerra, Paolo Scarpelli, Lara Macchioni, Bartolomeo Sebastiani, Antimo Gioiello, Rita Roberti. Selected cholesterol biosynthesis inhibitors produce accumulation of the intermediate FF-MAS that targets nucleus and activates LXRα in HepG2 cells. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2017 Sep; 1862(9):842-852. doi: 10.1016/j.bbalip.2017.05.004. [PMID: 28499814]
  • Josi Herron, Rosalyn C Reese, Keri A Tallman, Rohini Narayanaswamy, Ned A Porter, Libin Xu. Identification of Environmental Quaternary Ammonium Compounds as Direct Inhibitors of Cholesterol Biosynthesis. Toxicological sciences : an official journal of the Society of Toxicology. 2016 06; 151(2):261-70. doi: 10.1093/toxsci/kfw041. [PMID: 26919959]
  • Yoonhee Kim, Chaeyoung Kim, Hye Young Jang, Inhee Mook-Jung. Inhibition of Cholesterol Biosynthesis Reduces γ-Secretase Activity and Amyloid-β Generation. Journal of Alzheimer's disease : JAD. 2016; 51(4):1057-68. doi: 10.3233/jad-150982. [PMID: 26923021]
  • R Kennedy Keller, David A Mitchell, Christopher C Goulah, Steven J Fliesler. Hepatic isoprenoid metabolism in a rat model of Smith-Lemli-Opitz Syndrome. Lipids. 2013 Mar; 48(3):219-29. doi: 10.1007/s11745-013-3762-x. [PMID: 23361583]
  • Libin Xu, Wei Liu, Lowell G Sheflin, Steven J Fliesler, Ned A Porter. Novel oxysterols observed in tissues and fluids of AY9944-treated rats: a model for Smith-Lemli-Opitz syndrome. Journal of lipid research. 2011 Oct; 52(10):1810-20. doi: 10.1194/jlr.m018366. [PMID: 21817059]
  • Jana Sánchez-Wandelmer, Alberto Dávalos, Emilio Herrera, Martin Giera, Sonia Cano, Gema de la Peña, Miguel A Lasunción, Rebeca Busto. Inhibition of cholesterol biosynthesis disrupts lipid raft/caveolae and affects insulin receptor activation in 3T3-L1 preadipocytes. Biochimica et biophysica acta. 2009 Sep; 1788(9):1731-9. doi: 10.1016/j.bbamem.2009.05.002. [PMID: 19433058]
  • Jeanne Zhen Huo, Miguel A Cortez, O Carter Snead. GABA receptor proteins within lipid rafts in the AY-9944 model of atypical absence seizures. Epilepsia. 2009 Apr; 50(4):776-88. doi: 10.1111/j.1528-1167.2008.01903.x. [PMID: 19054408]
  • Eun-Young Lee, Pan-Young Jeong, Sun-Young Kim, Yhong-Hee Shim, David J Chitwood, Young-Ki Paik. Effects of sterols on the development and aging of Caenorhabditis elegans. Methods in molecular biology (Clifton, N.J.). 2009; 462(?):167-79. doi: 10.1007/978-1-60327-115-8_11. [PMID: 19160668]
  • Kathleen Boesze-Battaglia, Monika Damek-Poprawa, Drake C Mitchell, Laura Greeley, Richard S Brush, Robert E Anderson, Michael J Richards, Steven J Fliesler. Alteration of retinal rod outer segment membrane fluidity in a rat model of Smith-Lemli-Opitz syndrome. Journal of lipid research. 2008 Jul; 49(7):1488-99. doi: 10.1194/jlr.m800031-jlr200. [PMID: 18344409]
  • Yamuna Devi Paila, Mamidanna R V S Murty, Mariappanadar Vairamani, Amitabha Chattopadhyay. Signaling by the human serotonin(1A) receptor is impaired in cellular model of Smith-Lemli-Opitz Syndrome. Biochimica et biophysica acta. 2008 Jun; 1778(6):1508-16. doi: 10.1016/j.bbamem.2008.03.002. [PMID: 18381059]
  • David A Ford, Julie K Monda, Richard S Brush, Robert E Anderson, Michael J Richards, Steven J Fliesler. Lipidomic analysis of the retina in a rat model of Smith-Lemli-Opitz syndrome: alterations in docosahexaenoic acid content of phospholipid molecular species. Journal of neurochemistry. 2008 May; 105(3):1032-47. doi: 10.1111/j.1471-4159.2007.05203.x. [PMID: 18182048]
  • Jovita Ponce, Natalia Pérez de la Ossa, Olivia Hurtado, Mónica Millan, Juan F Arenillas, Antonio Dávalos, Teresa Gasull. Simvastatin reduces the association of NMDA receptors to lipid rafts: a cholesterol-mediated effect in neuroprotection. Stroke. 2008 Apr; 39(4):1269-75. doi: 10.1161/strokeaha.107.498923. [PMID: 18323503]
  • Yasuhisa Yamashita, Masahide Nishibori, Takato Terada, Naoki Isobe, Masayuki Shimada. Gonadotropin-induced delta14-reductase and delta7-reductase gene expression in cumulus cells during meiotic resumption of porcine oocytes. Endocrinology. 2005 Jan; 146(1):186-94. doi: 10.1210/en.2004-0617. [PMID: 15459117]
  • Irina Serbanescu, Mary Ann Ryan, Ruchika Shukla, Miguel A Cortez, O Carter Snead, Stephen C Cunnane. Lovastatin exacerbates atypical absence seizures with only minimal effects on brain sterols. Journal of lipid research. 2004 Nov; 45(11):2038-43. doi: 10.1194/jlr.m400097-jlr200. [PMID: 15314096]
  • R Kennedy Keller, Michael Small, Steven J Fliesler. Enzyme blockade: a nonradioactive method to determine the absolute rate of cholesterol synthesis in the brain. Journal of lipid research. 2004 Oct; 45(10):1952-7. doi: 10.1194/jlr.d400007-jlr200. [PMID: 15258193]
  • Steven J Fliesler, Neal S Peachey, Michael J Richards, Barbara A Nagel, Dana K Vaughan. Retinal degeneration in a rodent model of Smith-Lemli-Opitz syndrome: electrophysiologic, biochemical, and morphologic features. Archives of ophthalmology (Chicago, Ill. : 1960). 2004 Aug; 122(8):1190-200. doi: 10.1001/archopht.122.8.1190. [PMID: 15302661]
  • Marc Issandou, Raphaëlle Guillard, Anne-Benedicte Boullay, Valerie Linhart, Elvira Lopez-Perez. Up-regulation of low-density lipoprotein receptor in human hepatocytes is induced by sequestration of free cholesterol in the endosomal/lysosomal compartment. Biochemical pharmacology. 2004 Jun; 67(12):2281-9. doi: 10.1016/j.bcp.2004.03.006. [PMID: 15163559]
  • Huirong Xie, Guoliang Xia, Anne Grete Byskov, Claus Yding Andersen, Shumin Bo, Yong Tao. Roles of gonadotropins and meiosis-activating sterols in meiotic resumption of cultured follicle-enclosed mouse oocytes. Molecular and cellular endocrinology. 2004 Apr; 218(1-2):155-63. doi: 10.1016/j.mce.2003.11.030. [PMID: 15130520]
  • Vasan Persad, C Guin Ting Wong, Miguel A Cortez, Yu Tian Wang, O Carter Snead. Hormonal regulation of atypical absence seizures. Annals of neurology. 2004 Mar; 55(3):353-61. doi: 10.1002/ana.10831. [PMID: 14991813]
  • R Kennedy Keller, Thomas P Arnold, Steven J Fliesler. Formation of 7-dehydrocholesterol-containing membrane rafts in vitro and in vivo, with relevance to the Smith-Lemli-Opitz syndrome. Journal of lipid research. 2004 Feb; 45(2):347-55. doi: 10.1194/jlr.m300232-jlr200. [PMID: 14594996]
  • Miguel A Cortez, Stephen C Cunnane, O Carter Snead. Brain sterols in the AY-9944 rat model of atypical absence seizures. Epilepsia. 2002 Jan; 43(1):3-8. doi: 10.1046/j.1528-1157.2002.22401.x. [PMID: 11879380]
  • C Roux, C Wolf, N Mulliez, W Gaoua, V Cormier, F Chevy, D Citadelle. Role of cholesterol in embryonic development. The American journal of clinical nutrition. 2000 05; 71(5 Suppl):1270S-9S. doi: 10.1093/ajcn/71.5.1270s. [PMID: 10799401]
  • W Gaoua, C Wolf, F Chevy, F Ilien, C Roux. Cholesterol deficit but not accumulation of aberrant sterols is the major cause of the teratogenic activity in the Smith-Lemli-Opitz syndrome animal model. Journal of lipid research. 2000 Apr; 41(4):637-46. doi: 10.1016/s0022-2275(20)32412-3. [PMID: 10744785]
  • W Gaoua, F Chevy, C Roux, C Wolf. Oxidized derivatives of 7-dehydrocholesterol induce growth retardation in cultured rat embryos: a model for antenatal growth retardation in the Smith-Lemli-Opitz syndrome. Journal of lipid research. 1999 Mar; 40(3):456-63. doi: 10.1016/s0022-2275(20)32450-0. [PMID: 10064734]
  • C M Chambers, M P McLean, G C Ness. Smith-Lemli-Opitz syndrome produced in rats with AY 9944 treated by intravenous injection of lipoprotein cholesterol. American journal of medical genetics. 1997 Jan; 68(3):322-7. doi: 10.1002/(sici)1096-8628(19970131)68:3<322::aid-ajmg14>3.0.co;2-v. [PMID: 9024567]
  • B Llirbat, C Wolf, F Chevy, D Citadelle, G Bereziat, C Roux. Normal and inhibited cholesterol synthesis in the cultured rat embryo. Journal of lipid research. 1997 Jan; 38(1):22-34. doi: 10.1016/s0022-2275(20)37272-2. [PMID: 9034197]
  • M Kolf-Clauw, F Chevy, C Wolf, B Siliart, D Citadelle, C Roux. Inhibition of 7-dehydrocholesterol reductase by the teratogen AY9944: a rat model for Smith-Lemli-Opitz syndrome. Teratology. 1996 Sep; 54(3):115-25. doi: 10.1002/(sici)1096-9926(199609)54:3<115::aid-tera1>3.0.co;2-2. [PMID: 8987154]
  • C Wolf, F Chevy, J Pham, M Kolf-Clauw, D Citadelle, N Mulliez, C Roux. Changes in serum sterols of rats treated with 7-dehydrocholesterol-delta 7-reductase inhibitors: comparison to levels in humans with Smith-Lemli-Opitz syndrome. Journal of lipid research. 1996 Jun; 37(6):1325-33. doi: NULL. [PMID: 8808767]
  • W M Pandak, Z R Vlahcevic, D M Heuman, P B Hylemon. Regulation of bile acid synthesis. V. Inhibition of conversion of 7-dehydrocholesterol to cholesterol is associated with down-regulation of cholesterol 7 alpha-hydroxylase activity and inhibition of bile acid synthesis. Journal of lipid research. 1990 Dec; 31(12):2149-58. doi: . [PMID: 1708805]
  • M Repetto, J C Maziere, D Citadelle, R Dupuis, M Meier, S Biade, D Quiec, C Roux. Teratogenic effect of the cholesterol synthesis inhibitor AY 9944 on rat embryos in vitro. Teratology. 1990 Dec; 42(6):611-8. doi: 10.1002/tera.1420420605. [PMID: 1708171]
  • C Rampini, C Adriambinintsoa, V Barbu, J C Maziere, C Maziere, C Roux. Combined effects of AY9944 and plasma LDL (or whole plasma) on lymphocyte blastic transformation. Biochemical pharmacology. 1989 Nov; 38(21):3887-91. doi: 10.1016/0006-2952(89)90601-1. [PMID: 2480790]
  • V Barbu, C Roux, D Lambert, R Dupuis, J Gardette, J C Maziere, C Maziere, E Elefant, J Polonovski. Cholesterol prevents the teratogenic action of AY 9944: importance of the timing of cholesterol supplementation to rats. The Journal of nutrition. 1988 Jun; 118(6):774-9. doi: 10.1093/jn/118.6.774. [PMID: 2453625]
  • S Kacew, M J Reasor. Newborn response to cationic amphiphilic drugs. Federation proceedings. 1985 Apr; 44(7):2323-7. doi: . [PMID: 2579857]
  • V Barbu, C Roux, R Dupuis, J Gardette, J C Maziere. Teratogenic effect of AY 9944 in rats: importance of the day of administration and maternal plasma cholesterol level. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1984 May; 176(1):54-9. doi: 10.3181/00379727-176-41842. [PMID: 6200888]
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  • G Kay, P A Wilce. Inhibition of sterol and DNA synthesis in peripheral blood lymphocytes by AY9944. Biochemical and biophysical research communications. 1983 Jan; 110(1):82-7. doi: 10.1016/0006-291x(83)91263-9. [PMID: 6188453]
  • K M Botham, G S Boyd. The effect of the hypocholesteremic drug, AY 9944 on the synthesis of bile salts in rat liver. European journal of biochemistry. 1981 Sep; 118(3):501-5. doi: 10.1111/j.1432-1033.1981.tb05547.x. [PMID: 6170514]
  • H Tojo, T M Huston. Effects of steroid blockers on LH-induced ovulation in the domestic fowl, Gallus domesticus. Journal of reproduction and fertility. 1981 Mar; 61(2):381-6. doi: 10.1530/jrf.0.0610381. [PMID: 6162953]
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  • B F Rice, L M Roth, F E Cole, A A MacPhee, K Davis, R L Ponthier, W H Sternberg. Hypercalcemia and neoplasia. Biologic, biochemical, and ultrastructural studies of a hypercalcemia-producing Leydig cell tumor of the rat. Laboratory investigation; a journal of technical methods and pathology. 1975 Oct; 33(4):428-39. doi: NULL. [PMID: 52757]
  • M L GIVNER, D DVORNIK. AGENTS AFFECTING LIPID METABOLISM. XV. BIOCHEMICAL STUDIES WITH THE CHOLESTEROL BIOSYNTHESIS INHIBITOR AY-9944 IN YOUNG AND MATURE RATS. Biochemical pharmacology. 1965 Apr; 14(?):611-9. doi: 10.1016/0006-2952(65)90233-9. [PMID: 14322980]
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