5-(N,N-Hexamethylene)amiloride (BioDeep_00000393131)
代谢物信息卡片
化学式: C12H18ClN7O (311.1261288)
中文名称: 5-(N,N-六亚甲基)阿米洛利
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1CCCN(CC1)C2=NC(=C(N=C2Cl)C(=O)N=C(N)N)N
InChI: InChI=1S/C12H18ClN7O/c13-8-10(20-5-3-1-2-4-6-20)18-9(14)7(17-8)11(21)19-12(15)16/h1-6H2,(H2,14,18)(H4,15,16,19,21)
描述信息
D000970 - Antineoplastic Agents
同义名列表
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:76400
- PubChem: 1794
- ChEMBL: CHEMBL501701
- CAS: 1345839-29-3
- CAS: 1428-95-1
- PMhub: MS000243462
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
- Noah H Somberg, João Medeiros-Silva, Hyunil Jo, Jun Wang, William F DeGrado, Mei Hong. Hexamethylene amiloride binds the SARS-CoV-2 envelope protein at the protein-lipid interface.
Protein science : a publication of the Protein Society.
2023 10; 32(10):e4755. doi:
10.1002/pro.4755
. [PMID: 37632140] - Kiem Vu, Benjamin J Buckley, Richard S Bujaroski, Eduardo Blumwald, Michael J Kelso, Angie Gelli. Antifungal activity of 6-substituted amiloride and hexamethylene amiloride (HMA) analogs.
Frontiers in cellular and infection microbiology.
2023; 13(?):1101568. doi:
10.3389/fcimb.2023.1101568
. [PMID: 36923593] - Trine Lisberg Toft-Bertelsen, Mads Gravers Jeppesen, Eva Tzortzini, Kai Xue, Karin Giller, Stefan Becker, Amer Mujezinovic, Bo Hjorth Bentzen, Loren B Andreas, Antonios Kolocouris, Thomas Nitschke Kledal, Mette Marie Rosenkilde. Amantadine has potential for the treatment of COVID-19 because it inhibits known and novel ion channels encoded by SARS-CoV-2.
Communications biology.
2021 12; 4(1):1347. doi:
10.1038/s42003-021-02866-9
. [PMID: 34853399] - Benjamin J Buckley, Ashraf Aboelela, Hiwa Majed, Richard S Bujaroski, Karen L White, Andrew K Powell, Wen Wang, Kasiram Katneni, Jessica Saunders, David M Shackleford, Susan A Charman, Gregory M Cook, Michael J Kelso, Marie Ranson. Systematic evaluation of structure-property relationships and pharmacokinetics in 6-(hetero)aryl-substituted matched pair analogs of amiloride and 5-(N,N-hexamethylene)amiloride.
Bioorganic & medicinal chemistry.
2021 05; 37(?):116116. doi:
10.1016/j.bmc.2021.116116
. [PMID: 33799173] - 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] - Venkata S Mandala, Matthew J McKay, Alexander A Shcherbakov, Aurelio J Dregni, Antonios Kolocouris, Mei Hong. Structure and drug binding of the SARS-CoV-2 envelope protein transmembrane domain in lipid bilayers.
Nature structural & molecular biology.
2020 12; 27(12):1202-1208. doi:
10.1038/s41594-020-00536-8
. [PMID: 33177698] - Leandro Rocha Silva, Paulo Fernando da Silva Santos-Júnior, Júlia de Andrade Brandão, Letícia Anderson, Ênio José Bassi, João Xavier de Araújo-Júnior, Sílvia Helena Cardoso, Edeildo Ferreira da Silva-Júnior. Druggable targets from coronaviruses for designing new antiviral drugs.
Bioorganic & medicinal chemistry.
2020 11; 28(22):115745. doi:
10.1016/j.bmc.2020.115745
. [PMID: 33007557] - Carmen Aravena, Ana R Beltrán, Marcelo Cornejo, Viviana Torres, Emilce S Díaz, Enrique Guzmán-Gutiérrez, Fabián Pardo, Andrea Leiva, Luis Sobrevia, Marco A Ramírez. Potential role of sodium-proton exchangers in the low concentration arsenic trioxide-increased intracellular pH and cell proliferation.
PloS one.
2012; 7(12):e51451. doi:
10.1371/journal.pone.0051451
. [PMID: 23236503] - Roland Montserret, Nathalie Saint, Christophe Vanbelle, Andrés Gerardo Salvay, Jean-Pierre Simorre, Christine Ebel, Nicolas Sapay, Jean-Guillaume Renisio, Anja Böckmann, Eike Steinmann, Thomas Pietschmann, Jean Dubuisson, Christophe Chipot, François Penin. NMR structure and ion channel activity of the p7 protein from hepatitis C virus.
The Journal of biological chemistry.
2010 Oct; 285(41):31446-61. doi:
10.1074/jbc.m110.122895
. [PMID: 20667830] - Konstantin Pervushin, Edward Tan, Krupakar Parthasarathy, Xin Lin, Feng Li Jiang, Dejie Yu, Ardcharaporn Vararattanavech, Tuck Wah Soong, Ding Xiang Liu, Jaume Torres. Structure and inhibition of the SARS coronavirus envelope protein ion channel.
PLoS pathogens.
2009 Jul; 5(7):e1000511. doi:
10.1371/journal.ppat.1000511
. [PMID: 19593379] - Lauren Wilson, Peter Gage, Gary Ewart. Hexamethylene amiloride blocks E protein ion channels and inhibits coronavirus replication.
Virology.
2006 Sep; 353(2):294-306. doi:
10.1016/j.virol.2006.05.028
. [PMID: 16815524] - A Premkumar, C R Horan, P W Gage. Dengue virus M protein C-terminal peptide (DVM-C) forms ion channels.
The Journal of membrane biology.
2005 Mar; 204(1):33-8. doi:
10.1007/s00232-005-0744-9
. [PMID: 16007501] - A Premkumar, L Wilson, G D Ewart, P W Gage. Cation-selective ion channels formed by p7 of hepatitis C virus are blocked by hexamethylene amiloride.
FEBS letters.
2004 Jan; 557(1-3):99-103. doi:
10.1016/s0014-5793(03)01453-4
. [PMID: 14741348] - A D Hibell, K M Thompson, M Xing, P P Humphrey, A D Michel. Complexities of measuring antagonist potency at P2X(7) receptor orthologs.
The Journal of pharmacology and experimental therapeutics.
2001 Mar; 296(3):947-57. doi:
NULL
. [PMID: 11181928] - L Vroye, R Beauwens, J Van Sande, D Daloze, J C Braekman, P E Golstein. The Na+-I- cotransporter of the thyroid: characterisation of new inhibitors.
Pflugers Archiv : European journal of physiology.
1998 Jan; 435(2):259-66. doi:
10.1007/pl00008081
. [PMID: 9382940] - S Yamaguchi, M Tamagawa, N Nakajima, H Nakaya. Selective impairment of HCO3(-)-dependent pHi regulation by lysophosphatidylcholine in guinea pig ventricular myocardium.
Cardiovascular research.
1998 Jan; 37(1):179-86. doi:
10.1016/s0008-6363(97)00203-4
. [PMID: 9539872] - M L Barreto-Chaves, M de Mello-Aires. Luminal arginine vasopressin stimulates Na(+)-H+ exchange and H(+)-ATPase in cortical distal tubule via V1 receptor.
Kidney international.
1997 Oct; 52(4):1035-41. doi:
10.1038/ki.1997.425
. [PMID: 9328942] - M L Barreto-Chaves, M Mello-Aires. Effect of luminal angiotensin II and ANP on early and late cortical distal tubule HCO3- reabsorption.
The American journal of physiology.
1996 Nov; 271(5 Pt 2):F977-84. doi:
10.1152/ajprenal.1996.271.5.f977
. [PMID: 8945991] - N A Rebouças, G Malnic. Regulation of rat proximal tubule Na/H exchange by protein kinase C.
Kidney & blood pressure research.
1996; 19(2):87-93. doi:
10.1159/000174049
. [PMID: 8871887] - J H Ravesloot, T Eisen, R Baron, W F Boron. Role of Na-H exchangers and vacuolar H+ pumps in intracellular pH regulation in neonatal rat osteoclasts.
The Journal of general physiology.
1995 Feb; 105(2):177-208. doi:
10.1085/jgp.105.2.177
. [PMID: 7760016] - C W Song, G E Kim, J C Lyons, C M Makepeace, R J Griffin, G H Rao, E J Cragoe. Thermosensitization by increasing intracellular acidity with amiloride and its analogs.
International journal of radiation oncology, biology, physics.
1994 Dec; 30(5):1161-9. doi:
10.1016/0360-3016(94)90324-7
. [PMID: 7961026] - J Luo, I F Tannock. Inhibition of the regulation of intracellular pH: potential of 5-(N,N-hexamethylene) amiloride in tumour-selective therapy.
British journal of cancer.
1994 Oct; 70(4):617-24. doi:
10.1038/bjc.1994.360
. [PMID: 7917906] - Y F Chen, R H Yang, Q C Meng, E J Cragoe, S Oparil. Sodium-proton (Na+/H+) exchange inhibition increases blood pressure in spontaneously hypertensive rat.
The American journal of the medical sciences.
1994 Sep; 308(3):145-51. doi:
10.1097/00000441-199409000-00004
. [PMID: 8074129] - L C Nuttle, G R Dubyak. Differential activation of cation channels and non-selective pores by macrophage P2z purinergic receptors expressed in Xenopus oocytes.
The Journal of biological chemistry.
1994 May; 269(19):13988-96. doi:
. [PMID: 7514597]
- R Fernandez, M J Lopes, R F de Lira, W F Dantas, E J Cragoe Júnior, G Malnic. Mechanism of acidification along cortical distal tubule of the rat.
The American journal of physiology.
1994 Feb; 266(2 Pt 2):F218-26. doi:
10.1152/ajprenal.1994.266.2.f218
. [PMID: 8141323] - F I Wolf, A Di Francesco, A Cittadini. Characterization of magnesium efflux from Ehrlich ascites tumor cells.
Archives of biochemistry and biophysics.
1994 Feb; 308(2):335-41. doi:
10.1006/abbi.1994.1048
. [PMID: 7509147] - C W Song, J C Lyons, R J Griffin, C M Makepeace, E J Cragoe. Increase in thermosensitivity of tumor cells by lowering intracellular pH.
Cancer research.
1993 Apr; 53(7):1599-601. doi:
NULL
. [PMID: 8384080] - M R Holthe, O Brørs, E J Cragoe, T Veel, M Raeder. Determination of active 5-(N,N-hexamethylene)amiloride in pig plasma.
Journal of chromatography.
1992 Sep; 579(2):376-81. doi:
10.1016/0378-4347(92)80408-i
. [PMID: 1429989] - A L Wilson, S W Womble, C Prakash, E J Cragoe, I A Blair, L E Limbird. Novel amiloride analog allosterically modulates the alpha 2-adrenergic receptor but does not inhibit Na+/H+ exchange.
Molecular pharmacology.
1992 Aug; 42(2):175-9. doi:
NULL
. [PMID: 1325028] - D J Goldsmith, L Poston, M Watson, J Morris, P J Hilton, E J Cragoe. Effect of autologous serum on human leucocyte Na+/H+ exchange and intracellular pH.
Clinical science (London, England : 1979).
1990 Oct; 79(4):357-64. doi:
10.1042/cs0790357
. [PMID: 2171856] - B G Etscheid, G A Jamieson, K Toscas, M L Villereal. Loss of bradykinin receptors and TPA-stimulated Na+ influx in SV40-transformed WI-38 cells.
The American journal of physiology.
1990 Oct; 259(4 Pt 1):C549-56. doi:
10.1152/ajpcell.1990.259.4.c549
. [PMID: 2171345] - J J Grantham, J A Grantham, V S Donoso, E J Cragoe. Effect of amiloride on the compensatory renal growth that follows uninephrectomy in mice.
The Journal of laboratory and clinical medicine.
1989 Aug; 114(2):129-34. doi:
NULL
. [PMID: 2546998]