Alamethicin from Trichoderma viride (BioDeep_00000175818)

   

human metabolite blood metabolite


代谢物信息卡片


4-({3-carbamoyl-1-[(1-hydroxy-3-phenylpropan-2-yl)carbamoyl]propyl}carbamoyl)-4-(2-{2-[2-({1-[2-(2-{2-[2-(2-{2-[4-carbamoyl-2-(2-{2-[2-(2-{[1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl]formamido}-2-methylpropanamido)propanamido]-2-methylpropanamido}propanamido)butanamido]-2-methylpropanamido}-3-methylbutanamido)-2-methylpropanamido]acetamido}-4-methylpentanamido)-2-methylpropanoyl]pyrrolidin-2-yl}formamido)-3-methylbutanamido]-2-methylpropanamido}-2-methylpropanamido)butanoic acid

化学式: C92H150N22O25 (1963.1141930000001)
中文名称: 丙甲菌素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)CC(C(=O)NC(C)(C)C(=O)N1CCCC1C(=O)NC(C(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)N)C(=O)NC(CC2=CC=CC=C2)CO)NC(=O)CNC(=O)C(C)(C)NC(=O)C(C(C)C)NC(=O)C(C)(C)NC(=O)C(CCC(=O)N)NC(=O)C(C)NC(=O)C(C)(C)NC(=O)C(C)NC(=O)C(C)(C)NC(=O)C3CCCN3C(=O)C(C)(C)NC(=O)C
InChI: InChI=1S/C92H150N22O25/c1-47(2)43-58(72(127)108-92(24,25)84(139)113-41-29-33-59(113)73(128)103-65(48(3)4)75(130)111-90(20,21)82(137)112-89(18,19)80(135)102-56(37-40-64(120)121)70(125)101-55(35-38-61(93)117)69(124)98-54(46-115)44-53-31-27-26-28-32-53)99-63(119)45-95-77(132)85(10,11)110-76(131)66(49(5)6)104-81(136)88(16,17)107-71(126)57(36-39-62(94)118)100-67(122)50(7)96-78(133)86(12,13)106-68(123)51(8)97-79(134)87(14,15)109-74(129)60-34-30-42-114(60)83(138)91(22,23)105-52(9)116/h26-28,31-32,47-51,54-60,65-66,115H,29-30,33-46H2,1-25H3,(H2,93,117)(H2,94,118)(H,95,132)(H,96,133)(H,97,134)(H,98,124)(H,99,119)(H,100,122)(H,101,125)(H,102,135)(H,103,128)(H,104,136)(H,105,116)(H,106,123)(H,107,126)(H,108,127)(H,109,129)(H,110,131)(H,111,130)(H,112,137)(H,120,121)

描述信息

D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents
D004791 - Enzyme Inhibitors > D014475 - Uncoupling Agents
D049990 - Membrane Transport Modulators
D007476 - Ionophores
Alamethicin, isolated from Trichoderma viride, is a channel-forming peptide antibiotic and induces voltage-gated conductance in model and cell membranes[1][2].

同义名列表

3 个代谢物同义名

4-({3-carbamoyl-1-[(1-hydroxy-3-phenylpropan-2-yl)carbamoyl]propyl}carbamoyl)-4-(2-{2-[2-({1-[2-(2-{2-[2-(2-{2-[4-carbamoyl-2-(2-{2-[2-(2-{[1-(2-acetamido-2-methylpropanoyl)pyrrolidin-2-yl]formamido}-2-methylpropanamido)propanamido]-2-methylpropanamido}propanamido)butanamido]-2-methylpropanamido}-3-methylbutanamido)-2-methylpropanamido]acetamido}-4-methylpentanamido)-2-methylpropanoyl]pyrrolidin-2-yl}formamido)-3-methylbutanamido]-2-methylpropanamido}-2-methylpropanamido)butanoic acid; Alamethicin from Trichoderma viride; alamethicin



数据库引用编号

7 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)

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

  • Vladimir I Novoderezhkin, Tatyana I Rokitskaya, Elena A Kotova, Yuri N Antonenko. Synchronization of opening and closing of two gramicidin A channels pulled together by a linker: possible relevance to channel clustering. Physical chemistry chemical physics : PCCP. 2023 Feb; 25(5):3752-3757. doi: 10.1039/d2cp04884a. [PMID: 36644888]
  • Masato Kondoh, Arisa Sano, Izuru Kawamura, Taka-Aki Ishibashi. Total Internal Reflection Raman Spectra of Alamethicin Interacting with Supported Lipid Bilayers at a Silica/Water Interface. The journal of physical chemistry. B. 2022 12; 126(50):10712-10720. doi: 10.1021/acs.jpcb.2c06371. [PMID: 36440848]
  • Subhadeep Koner, Joseph Tawfik, Farzin Mashali, Kristen B Kennison, William T McClintic, Frederick A Heberle, Yu-Ming Tu, Manish Kumar, Stephen A Sarles. Homogeneous hybrid droplet interface bilayers assembled from binary mixtures of DPhPC phospholipids and PB-b-PEO diblock copolymers. Biochimica et biophysica acta. Biomembranes. 2022 10; 1864(10):183997. doi: 10.1016/j.bbamem.2022.183997. [PMID: 35718208]
  • Evgeniy Salnikov, Burkhard Bechinger. Effect of lipid saturation on the topology and oligomeric state of helical membrane polypeptides. Biochimica et biophysica acta. Biomembranes. 2022 10; 1864(10):184001. doi: 10.1016/j.bbamem.2022.184001. [PMID: 35817122]
  • ZhangFei Su, J Jay Leitch, Jacek Lipkowski. Effect of Lipid Composition on the Inhibition Mechanism of Amiloride on Alamethicin Ion Channels in Supported Phospholipid Bilayers. Langmuir : the ACS journal of surfaces and colloids. 2022 07; 38(27):8398-8406. doi: 10.1021/acs.langmuir.2c00953. [PMID: 35749587]
  • Allan G Rasmusson, Ian Max Møller, Susanne Widell. Assessment of Respiratory Enzymes in Intact Cells by Permeabilization with Alamethicin. Methods in molecular biology (Clifton, N.J.). 2022; 2363(?):77-84. doi: 10.1007/978-1-0716-1653-6_7. [PMID: 34545487]
  • Elizabeth G Kelley, Paul D Butler, Michihiro Nagao. Collective dynamics in lipid membranes containing transmembrane peptides. Soft matter. 2021 Jun; 17(23):5671-5681. doi: 10.1039/d1sm00314c. [PMID: 33942045]
  • Cameron C Hanna, Yann O Hermant, Paul W R Harris, Margaret A Brimble. Discovery, Synthesis, and Optimization of Peptide-Based Antibiotics. Accounts of chemical research. 2021 04; 54(8):1878-1890. doi: 10.1021/acs.accounts.0c00841. [PMID: 33750106]
  • Erin R Birdsall, Megan K Petti, Vivek Saraswat, Joshua S Ostrander, Michael S Arnold, Martin T Zanni. Structure Changes of a Membrane Polypeptide under an Applied Voltage Observed with Surface-Enhanced 2D IR Spectroscopy. The journal of physical chemistry letters. 2021 Feb; 12(7):1786-1792. doi: 10.1021/acs.jpclett.0c03706. [PMID: 33576633]
  • William T McClintic, Graham J Taylor, Michael L Simpson, C Patrick Collier. Macromolecular Crowding Affects Voltage-Dependent Alamethicin Pore Formation in Lipid Bilayer Membranes. The journal of physical chemistry. B. 2020 06; 124(25):5095-5102. doi: 10.1021/acs.jpcb.0c01650. [PMID: 32428410]
  • Hai-Jing Liu, Xin Wang, Zhi-Ling Yang, Lin-Ling Ren, Ting-Ting Qian. Identification and biochemical characterization of the glutathione reductase family from Populus trichocarpa. Plant science : an international journal of experimental plant biology. 2020 May; 294(?):110459. doi: 10.1016/j.plantsci.2020.110459. [PMID: 32234218]
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  • Raimo Mikkola, Maria Andersson, Ekaterina Kharechkina, Svetlana Kruglova, Alexey Kruglov. Fusaricidin-Type Compounds Create Pores in Mitochondrial and Plasma Membranes of Mammalian Cells. Biomolecules. 2019 09; 9(9):. doi: 10.3390/biom9090433. [PMID: 31480526]
  • Joseph S Najem, Graham J Taylor, Nick Armendarez, Ryan J Weiss, Md Sakib Hasan, Garrett S Rose, Catherine D Schuman, Alex Belianinov, Stephen A Sarles, C Patrick Collier. Assembly and Characterization of Biomolecular Memristors Consisting of Ion Channel-doped Lipid Membranes. Journal of visualized experiments : JoVE. 2019 03; ?(145):. doi: 10.3791/58998. [PMID: 30907866]
  • Graham Taylor, Mary-Anne Nguyen, Subhadeep Koner, Eric Freeman, C Patrick Collier, Stephen A Sarles. Electrophysiological interrogation of asymmetric droplet interface bilayers reveals surface-bound alamethicin induces lipid flip-flop. Biochimica et biophysica acta. Biomembranes. 2019 01; 1861(1):335-343. doi: 10.1016/j.bbamem.2018.07.001. [PMID: 30006208]
  • Mengke Zhang, Jinpeng Wang, Yuan Lyu, Maya Fitriyanti, Hu Hou, Zhengyu Jin, Xiao Zhu, Ganesan Narsimhan. Understanding the antimicrobial activity of water soluble γ-cyclodextrin/alamethicin complex. Colloids and surfaces. B, Biointerfaces. 2018 Dec; 172(?):451-458. doi: 10.1016/j.colsurfb.2018.08.065. [PMID: 30196230]
  • Fatemeh Abbasi, Julia Alvarez-Malmagro, ZhangFei Su, J Jay Leitch, Jacek Lipkowski. Pore Forming Properties of Alamethicin in Negatively Charged Floating Bilayer Lipid Membranes Supported on Gold Electrodes. Langmuir : the ACS journal of surfaces and colloids. 2018 11; 34(45):13754-13765. doi: 10.1021/acs.langmuir.8b02554. [PMID: 30265810]
  • Bradley R Dotson, Dia Soltan, John Schmidt, Mariam Areskoug, Kenny Rabe, Corné Swart, Susanne Widell, Allan G Rasmusson. The antibiotic peptaibol alamethicin from Trichoderma permeabilises Arabidopsis root apical meristem and epidermis but is antagonised by cellulase-induced resistance to alamethicin. BMC plant biology. 2018 Aug; 18(1):165. doi: 10.1186/s12870-018-1370-x. [PMID: 30097019]
  • ZhangFei Su, Muzaffar Shodiev, J Jay Leitch, Fatemeh Abbasi, Jacek Lipkowski. Role of Transmembrane Potential and Defects on the Permeabilization of Lipid Bilayers by Alamethicin, an Ion-Channel-Forming Peptide. Langmuir : the ACS journal of surfaces and colloids. 2018 05; 34(21):6249-6260. doi: 10.1021/acs.langmuir.8b00928. [PMID: 29722994]
  • Tomoko Mizuguchi, Nobuyuki Matubayasi. Free-Energy Analysis of Peptide Binding in Lipid Membrane Using All-Atom Molecular Dynamics Simulation Combined with Theory of Solutions. The journal of physical chemistry. B. 2018 04; 122(13):3219-3229. doi: 10.1021/acs.jpcb.7b08241. [PMID: 29320189]
  • Enrico Forbrig, Jana K Staffa, Johannes Salewski, Maria Andrea Mroginski, Peter Hildebrandt, Jacek Kozuch. Monitoring the Orientational Changes of Alamethicin during Incorporation into Bilayer Lipid Membranes. Langmuir : the ACS journal of surfaces and colloids. 2018 02; 34(6):2373-2385. doi: 10.1021/acs.langmuir.7b04265. [PMID: 29353482]
  • Catherine Adam, Anna D Peters, M Giovanna Lizio, George F S Whitehead, Vincent Diemer, James A Cooper, Scott L Cockroft, Jonathan Clayden, Simon J Webb. The Role of Terminal Functionality in the Membrane and Antibacterial Activity of Peptaibol-Mimetic Aib Foldamers. Chemistry (Weinheim an der Bergstrasse, Germany). 2018 Feb; 24(9):2249-2256. doi: 10.1002/chem.201705299. [PMID: 29210477]
  • Victoria N Syryamina, Marta De Zotti, Claudio Toniolo, Fernando Formaggio, Sergei A Dzuba. Alamethicin self-assembling in lipid membranes: concentration dependence from pulsed EPR of spin labels. Physical chemistry chemical physics : PCCP. 2018 Jan; 20(5):3592-3601. doi: 10.1039/c7cp07298h. [PMID: 29340383]
  • Joseph E Faust, Pei-Yin Yang, Huey W Huang. Action of Antimicrobial Peptides on Bacterial and Lipid Membranes: A Direct Comparison. Biophysical journal. 2017 Apr; 112(8):1663-1672. doi: 10.1016/j.bpj.2017.03.003. [PMID: 28445757]
  • Ekaterina F Afanasyeva, Victoria N Syryamina, Sergei A Dzuba. Communication: Alamethicin can capture lipid-like molecules in the membrane. The Journal of chemical physics. 2017 Jan; 146(1):011103. doi: 10.1063/1.4973703. [PMID: 28063425]
  • Evgeniy S Salnikov, Jesus Raya, Marta De Zotti, Ekaterina Zaitseva, Cristina Peggion, Gema Ballano, Claudio Toniolo, Jan Raap, Burkhard Bechinger. Alamethicin Supramolecular Organization in Lipid Membranes from 19F Solid-State NMR. Biophysical journal. 2016 Dec; 111(11):2450-2459. doi: 10.1016/j.bpj.2016.09.048. [PMID: 27926846]
  • Melanie A Ladd, Patrick N Fitzsimmons, John W Nichols. Optimization of a UDP-glucuronosyltransferase assay for trout liver S9 fractions: activity enhancement by alamethicin, a pore-forming peptide. Xenobiotica; the fate of foreign compounds in biological systems. 2016 Dec; 46(12):1066-1075. doi: 10.3109/00498254.2016.1149634. [PMID: 26947351]
  • Zahra Hemmatian, Scott Keene, Erik Josberger, Takeo Miyake, Carina Arboleda, Jessica Soto-Rodríguez, François Baneyx, Marco Rolandi. Electronic control of H+ current in a bioprotonic device with Gramicidin A and Alamethicin. Nature communications. 2016 10; 7(?):12981. doi: 10.1038/ncomms12981. [PMID: 27713411]
  • Sunita Meena, Jitender Mehla, Raj Kumar, S K Sood. Common Mechanism of Cross-Resistance Development in Pathogenic Bacteria Bacillus cereus Against Alamethicin and Pediocin Involves Alteration in Lipid Composition. Current microbiology. 2016 Oct; 73(4):534-41. doi: 10.1007/s00284-016-1090-0. [PMID: 27378130]
  • B Scott Perrin, Richard W Pastor. Simulations of Membrane-Disrupting Peptides I: Alamethicin Pore Stability and Spontaneous Insertion. Biophysical journal. 2016 Sep; 111(6):1248-1257. doi: 10.1016/j.bpj.2016.08.014. [PMID: 27653483]
  • Rolando Guidelli, Lucia Becucci. Mechanism of voltage-gated channel formation in lipid membranes. Biochimica et biophysica acta. 2016 Apr; 1858(4):748-55. doi: 10.1016/j.bbamem.2015.12.035. [PMID: 26768224]
  • Wei-Ling Shi, Xiu-Lan Chen, Li-Xia Wang, Zhi-Ting Gong, Shuyu Li, Chun-Long Li, Bin-Bin Xie, Wei Zhang, Mei Shi, Chuanyou Li, Yu-Zhong Zhang, Xiao-Yan Song. Cellular and molecular insight into the inhibition of primary root growth of Arabidopsis induced by peptaibols, a class of linear peptide antibiotics mainly produced by Trichoderma spp. Journal of experimental botany. 2016 Apr; 67(8):2191-205. doi: 10.1093/jxb/erw023. [PMID: 26850879]
  • Kenneth J Barns, James C Weisshaar. Single-cell, time-resolved study of the effects of the antimicrobial peptide alamethicin on Bacillus subtilis. Biochimica et biophysica acta. 2016 Apr; 1858(4):725-32. doi: 10.1016/j.bbamem.2016.01.003. [PMID: 26777771]
  • Victoria I Bunik, Artem Artiukhov, Alexey Kazantsev, Renata Goncalves, Danilo Daloso, Henry Oppermann, Elena Kulakovskaya, Nikolay Lukashev, Alisdair Fernie, Martin Brand, Frank Gaunitz. Specific inhibition by synthetic analogs of pyruvate reveals that the pyruvate dehydrogenase reaction is essential for metabolism and viability of glioblastoma cells. Oncotarget. 2015 Nov; 6(37):40036-52. doi: 10.18632/oncotarget.5486. [PMID: 26503465]
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  • Sara Bobone, Marta De Zotti, Annalisa Bortolotti, Barbara Biondi, Gema Ballano, Antonio Palleschi, Claudio Toniolo, Fernando Formaggio, Lorenzo Stella. The fluorescence and infrared absorption probe para-cyanophenylalanine: Effect of labeling on the behavior of different membrane-interacting peptides. Biopolymers. 2015 Sep; 104(5):521-32. doi: 10.1002/bip.22674. [PMID: 25968959]
  • Yuan Zhou, Ping Dong, Yanqi Wei, Jun Qian, Daoben Hua. Synthesis of poly(sulfobetaine methacrylate)-grafted chitosan under γ-ray irradiation for alamethicin assembly. Colloids and surfaces. B, Biointerfaces. 2015 Aug; 132(?):132-7. doi: 10.1016/j.colsurfb.2015.05.019. [PMID: 26037702]
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