Myxothiazol (BioDeep_00000010826)

   


代谢物信息卡片


Myxothiazol A

化学式: C25H33N3O3S2 (487.1963)
中文名称: 粘噻唑
谱图信息: 最多检出来源 Homo sapiens(not specific) 50%

分子结构信息

SMILES: CC(C)C=CC=CC(C)C1=NC(=CS1)C2=NC(=CS2)C=CC(C(C)C(=CC(=O)N)OC)OC
InChI: InChI=1S/C25H33N3O3S2/c1-16(2)9-7-8-10-17(3)24-28-20(15-33-24)25-27-19(14-32-25)11-12-21(30-5)18(4)22(31-6)13-23(26)29/h7-18,21H,1-6H3,(H2,26,29)/b9-7+,10-8+,12-11+,22-13+/t17-,18+,21-/m0/s1

描述信息

A 2,4-bi-1,3-thiazole substituted at the 4-position with a (1E,3S,4R,5E)-7-amino-3,5-dimethoxy-4-methyl-7-oxohepta-1,5-dien-1-yl] group and at the 2-position with a (2S,3E,5E)-7-methylocta-3,5-dien-2-yl group. It is an inhibitor of coenzyme Q - cytochrome c reductase.
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
D004791 - Enzyme Inhibitors

同义名列表

3 个代谢物同义名

Myxothiazol; Myxothiazol A; Myxothiazol A



数据库引用编号

15 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)

3 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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 ATF4, AXIN2, BCL2, CAT, GUCY1A1, HIF1A, MELK, NOS3, VEGFA
Peripheral membrane protein 3 HSD17B6, MELK, NDUFA5
Endoplasmic reticulum membrane 1 BCL2
Nucleus 8 ATF4, AXIN2, BCL2, CYC1, HIF1A, MXD3, NOS3, VEGFA
cytosol 8 ATF4, AXIN2, BCL2, CAT, GUCY1A1, HIF1A, NOS3, PRKCQ
nuclear body 1 HIF1A
centrosome 2 ATF4, AXIN2
nucleoplasm 4 ATF4, ATP2B1, HIF1A, NOS3
RNA polymerase II transcription regulator complex 3 ATF4, HIF1A, MXD3
Cell membrane 4 ATF4, ATP2B1, MELK, TNF
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 2 ATP2B1, MT-CYB
Synapse 1 ATP2B1
cell cortex 1 MELK
cell surface 2 TNF, VEGFA
glutamatergic synapse 2 ATP2B1, GUCY1A1
Golgi apparatus 2 NOS3, VEGFA
Golgi membrane 2 INS, NOS3
mitochondrial inner membrane 4 ATP5ME, CYC1, MT-CYB, NDUFA5
neuronal cell body 1 TNF
presynaptic membrane 1 ATP2B1
plasma membrane 6 ATP2B1, AXIN2, MELK, NOS3, PRKCQ, TNF
synaptic vesicle membrane 1 ATP2B1
Membrane 7 ATP2B1, BCL2, CAT, CYC1, MELK, MT-CYB, VEGFA
basolateral plasma membrane 1 ATP2B1
caveola 1 NOS3
extracellular exosome 3 ATP2B1, CAT, SOD2
Lumenal side 1 HSD17B6
endoplasmic reticulum 3 BCL2, HSD17B6, VEGFA
extracellular space 3 INS, TNF, VEGFA
perinuclear region of cytoplasm 1 NOS3
adherens junction 1 VEGFA
mitochondrion 7 ATP5ME, BCL2, CAT, CYC1, MT-CYB, NDUFA5, SOD2
protein-containing complex 4 ATF4, BCL2, CAT, HIF1A
intracellular membrane-bounded organelle 3 ATP2B1, CAT, HSD17B6
Microsome membrane 1 HSD17B6
Secreted 2 INS, VEGFA
extracellular region 4 CAT, INS, TNF, VEGFA
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, CYC1
mitochondrial outer membrane 1 BCL2
Mitochondrion matrix 1 SOD2
mitochondrial matrix 2 CAT, SOD2
centriolar satellite 1 PRKCQ
motile cilium 1 HIF1A
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 ATF4
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
beta-catenin destruction complex 1 AXIN2
axon cytoplasm 1 HIF1A
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Mitochondrion inner membrane 3 CYC1, MT-CYB, NDUFA5
Matrix side 1 NDUFA5
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 CAT
GABA-ergic synapse 1 GUCY1A1
extracellular matrix 1 VEGFA
mitochondrial nucleoid 1 SOD2
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 VEGFA
lateral plasma membrane 1 ATP2B1
nuclear speck 2 ATF4, HIF1A
neuron projection 1 ATF4
chromatin 3 ATF4, HIF1A, MXD3
cell projection 1 ATP2B1
phagocytic cup 1 TNF
cytoskeleton 1 NOS3
Basolateral cell membrane 1 ATP2B1
endosome lumen 1 INS
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
Nucleus speckle 2 ATF4, HIF1A
euchromatin 1 HIF1A
Presynaptic cell membrane 1 ATP2B1
myelin sheath 1 BCL2
respiratory chain complex I 1 NDUFA5
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
platelet alpha granule lumen 1 VEGFA
endocytic vesicle membrane 1 NOS3
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 2 ATP2B1, PRKCQ
aggresome 1 PRKCQ
respiratory chain complex III 2 CYC1, MT-CYB
dendrite membrane 1 ATF4
guanylate cyclase complex, soluble 1 GUCY1A1
nuclear periphery 1 ATF4
proton-transporting ATP synthase complex 1 ATP5ME
proton-transporting ATP synthase complex, coupling factor F(o) 1 ATP5ME
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
BAD-BCL-2 complex 1 BCL2
photoreceptor ribbon synapse 1 ATP2B1
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
ATF4-CREB1 transcription factor complex 1 ATF4
ATF1-ATF4 transcription factor complex 1 ATF4
CHOP-ATF4 complex 1 ATF4
Lewy body core 1 ATF4
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yanqiao Zhu, Reena Narsai, Cunman He, Yan Wang, Oliver Berkowitz, James Whelan, Lim Chee Liew. Coordinated regulation of the mitochondrial retrograde response by circadian clock regulators and ANAC017. Plant communications. 2023 Jan; 4(1):100501. doi: 10.1016/j.xplc.2022.100501. [PMID: 36463409]
  • Nicolas Melis, Romain Carcy, Isabelle Rubera, Marc Cougnon, Christophe Duranton, Michel Tauc, Didier F Pisani. Akt Inhibition as Preconditioning Treatment to Protect Kidney Cells against Anoxia. International journal of molecular sciences. 2021 Dec; 23(1):. doi: 10.3390/ijms23010152. [PMID: 35008578]
  • Seán M Kilbride, Jayne E Telford, Gavin P Davey. Complex I Controls Mitochondrial and Plasma Membrane Potentials in Nerve Terminals. Neurochemical research. 2021 Jan; 46(1):100-107. doi: 10.1007/s11064-020-02990-8. [PMID: 32130629]
  • Yu-Ting Li, Mei-Jun Liu, Ying Li, Peng Liu, Shi-Jie Zhao, Hui-Yuan Gao, Zi-Shan Zhang. Photoprotection by mitochondrial alternative pathway is enhanced at heat but disabled at chilling. The Plant journal : for cell and molecular biology. 2020 10; 104(2):403-415. doi: 10.1111/tpj.14931. [PMID: 32683757]
  • Nicole A Alber, Greg C Vanlerberghe. Signaling interactions between mitochondria and chloroplasts in Nicotiana tabacum leaf. Physiologia plantarum. 2019 Oct; 167(2):188-204. doi: 10.1111/ppl.12879. [PMID: 30467859]
  • Veronika Zelinová, Loriana Demecsová, Ladislav Tamás. Impact of antimycin A and myxothiazol on cadmium-induced superoxide, hydrogen peroxide, and nitric oxide generation in barley root tip. Protoplasma. 2019 Sep; 256(5):1375-1383. doi: 10.1007/s00709-019-01389-9. [PMID: 31079230]
  • Nicole A Alber, Hampavi Sivanesan, Greg C Vanlerberghe. The occurrence and control of nitric oxide generation by the plant mitochondrial electron transport chain. Plant, cell & environment. 2017 Jul; 40(7):1074-1085. doi: 10.1111/pce.12884. [PMID: 27987212]
  • Sebastian Schieferdecker, Thomas E Exner, Harald Gross, Martin Roth, Markus Nett. New myxothiazols from the predatory bacterium Myxococcus fulvus. The Journal of antibiotics. 2014 Jul; 67(7):519-25. doi: 10.1038/ja.2014.31. [PMID: 24690915]
  • Mina Davoudi, Jukka Kallijärvi, Sanna Marjavaara, Heike Kotarsky, Eva Hansson, Per Levéen, Vineta Fellman. A mouse model of mitochondrial complex III dysfunction induced by myxothiazol. Biochemical and biophysical research communications. 2014 Apr; 446(4):1079-84. doi: 10.1016/j.bbrc.2014.03.058. [PMID: 24661880]
  • Fraser D Russell, Karina D Hamilton. Nutrient deprivation increases vulnerability of endothelial cells to proinflammatory insults. Free radical biology & medicine. 2014 Feb; 67(?):408-15. doi: 10.1016/j.freeradbiomed.2013.12.007. [PMID: 24334251]
  • Nam-Hoon Kim, Bong-Ki Hong, Soo Youn Choi, Hyug Moo Kwon, Chul-Soo Cho, Eugene C Yi, Wan-Uk Kim. Reactive oxygen species regulate context-dependent inhibition of NFAT5 target genes. Experimental & molecular medicine. 2013 Jul; 45(?):e32. doi: 10.1038/emm.2013.61. [PMID: 23867654]
  • Sheo B Singh, Weiguo Liu, Xiaohua Li, Tom Chen, Ali Shafiee, Deborah Card, George Abruzzo, Amy Flattery, Charles Gill, John R Thompson, Mark Rosenbach, Sarah Dreikorn, Viktor Hornak, Maria Meinz, Myra Kurtz, Rosemarie Kelly, Janet C Onishi. Antifungal spectrum, in vivo efficacy, and structure-activity relationship of ilicicolin h. ACS medicinal chemistry letters. 2012 Oct; 3(10):814-7. doi: 10.1021/ml300173e. [PMID: 24900384]
  • Minoru Satoh, Sohachi Fujimoto, Hideyuki Horike, Masahito Ozeki, Hajime Nagasu, Naruya Tomita, Tamaki Sasaki, Naoki Kashihara. Mitochondrial damage-induced impairment of angiogenesis in the aging rat kidney. Laboratory investigation; a journal of technical methods and pathology. 2011 Feb; 91(2):190-202. doi: 10.1038/labinvest.2010.175. [PMID: 20921951]
  • Cleverson Busso, Erich B Tahara, Renata Ogusucu, Ohara Augusto, Jose Ribamar Ferreira-Junior, Alexander Tzagoloff, Alicia J Kowaltowski, Mario H Barros. Saccharomyces cerevisiae coq10 null mutants are responsive to antimycin A. The FEBS journal. 2010 Nov; 277(21):4530-8. doi: 10.1111/j.1742-4658.2010.07862.x. [PMID: 20875086]
  • Claudio Coddou, Juan F Codocedo, Shuo Li, Juan G Lillo, Claudio Acuña-Castillo, Paulina Bull, Stanko S Stojilkovic, J Pablo Huidobro-Toro. Reactive oxygen species potentiate the P2X2 receptor activity through intracellular Cys430. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2009 Sep; 29(39):12284-91. doi: 10.1523/jneurosci.2096-09.2009. [PMID: 19793987]
  • Patries M Herst, Michael V Berridge. Cell surface oxygen consumption: a major contributor to cellular oxygen consumption in glycolytic cancer cell lines. Biochimica et biophysica acta. 2007 Feb; 1767(2):170-7. doi: 10.1016/j.bbabio.2006.11.018. [PMID: 17266920]
  • Tsuyoshi Sugio, Tomohiro Hisazumi, Tadayoshi Kanao, Kazuo Kamimura, Fumiaki Takeuchi, Atsunori Negishi. Existence of aa3-type ubiquinol oxidase as a terminal oxidase in sulfite oxidation of Acidithiobacillus thiooxidans. Bioscience, biotechnology, and biochemistry. 2006 Jul; 70(7):1584-91. doi: 10.1271/bbb.50623. [PMID: 16861791]
  • Xiaoming Zhou, Joan D Ferraris, Maurice B Burg. Mitochondrial reactive oxygen species contribute to high NaCl-induced activation of the transcription factor TonEBP/OREBP. American journal of physiology. Renal physiology. 2006 May; 290(5):F1169-76. doi: 10.1152/ajprenal.00378.2005. [PMID: 16303854]
  • Boris V Chernyak, Denis S Izyumov, Konstantin G Lyamzaev, Alina A Pashkovskaya, Olga Y Pletjushkina, Yuri N Antonenko, Dmitrii V Sakharov, Karel W A Wirtz, Vladimir P Skulachev. Production of reactive oxygen species in mitochondria of HeLa cells under oxidative stress. Biochimica et biophysica acta. 2006 May; 1757(5-6):525-34. doi: 10.1016/j.bbabio.2006.02.019. [PMID: 16678116]
  • Kapuganti Jagadis Gupta, Maria Stoimenova, Werner M Kaiser. In higher plants, only root mitochondria, but not leaf mitochondria reduce nitrite to NO, in vitro and in situ. Journal of experimental botany. 2005 Oct; 56(420):2601-9. doi: 10.1093/jxb/eri252. [PMID: 16131511]
  • Alfredo Guéra, Angeles Calatayud, Bartolomé Sabater, Eva Barreno. Involvement of the thylakoidal NADH-plastoquinone-oxidoreductase complex in the early responses to ozone exposure of barley (Hordeum vulgare L.) seedlings. Journal of experimental botany. 2005 Jan; 56(409):205-18. doi: 10.1093/jxb/eri024. [PMID: 15557294]
  • Ivan Nalvarte, Anastasios E Damdimopoulos, Giannis Spyrou. Human mitochondrial thioredoxin reductase reduces cytochrome c and confers resistance to complex III inhibition. Free radical biology & medicine. 2004 May; 36(10):1270-8. doi: 10.1016/j.freeradbiomed.2004.02.072. [PMID: 15110392]
  • Vitaly D Samuilov, Elena M Lagunova, Dmitry B Kiselevsky, Elena V Dzyubinskaya, Yana V Makarova, Mikhail V Gusev. Participation of chloroplasts in plant apoptosis. Bioscience reports. 2003 Apr; 23(2-3):103-17. doi: 10.1023/a:1025576307912. [PMID: 14570380]
  • Kirsten E Tollefson, James Kroczynski, Michael V Cutaia. Time-dependent interactions of oxidant-sensitive fluoroprobes with inhibitors of cellular metabolism. Laboratory investigation; a journal of technical methods and pathology. 2003 Mar; 83(3):367-75. doi: 10.1097/01.lab.0000059934.53602.4f. [PMID: 12649337]
  • Laurent Cournac, Gwendal Latouche, Zoran Cerovic, Kevin Redding, Jacques Ravenel, Gilles Peltier. In vivo interactions between photosynthesis, mitorespiration, and chlororespiration in Chlamydomonas reinhardtii. Plant physiology. 2002 Aug; 129(4):1921-8. doi: 10.1104/pp.001636. [PMID: 12177506]
  • Wieslawa Jarmuszkiewicz, Francis E Sluse, Lilla Hryniewiecka, Claudine M Sluse-Goffart. Interactions between the cytochrome pathway and the alternative oxidase in isolated Acanthamoeba castellanii mitochondria. Journal of bioenergetics and biomembranes. 2002 Feb; 34(1):31-40. doi: 10.1023/a:1013866603094. [PMID: 11860178]
  • T Joët, L Cournac, E M Horvath, P Medgyesy, G Peltier. Increased sensitivity of photosynthesis to antimycin A induced by inactivation of the chloroplast ndhB gene. Evidence for a participation of the NADH-dehydrogenase complex to cyclic electron flow around photosystem I. Plant physiology. 2001 Apr; 125(4):1919-29. doi: 10.1104/pp.125.4.1919. [PMID: 11299371]
  • M Waśniewska, J Duszyński. The role of mitochondrial dysfunction in regulation of store-operated calcium channels in glioma C6 and human fibroblast cells. FEBS letters. 2000 Aug; 478(3):237-40. doi: 10.1016/s0014-5793(00)01862-7. [PMID: 10930575]
  • V M Ortega, J G Bohner, C D Chase. The tobacco apocytochrome b gene predicts sensitivity to the respiratory inhibitors antimycin A and myxothiazol. Current genetics. 2000 May; 37(5):315-21. doi: 10.1007/s002940050533. [PMID: 10853768]
  • A Makowska, K Zablocki, J Duszyński. The role of mitochondria in the regulation of calcium influx into Jurkat cells. European journal of biochemistry. 2000 Feb; 267(3):877-84. doi: 10.1046/j.1432-1327.2000.01066.x. [PMID: 10651826]
  • B Gomez, N C Robinson. Phospholipase digestion of bound cardiolipin reversibly inactivates bovine cytochrome bc1. Biochemistry. 1999 Jul; 38(28):9031-8. doi: 10.1021/bi990603r. [PMID: 10413476]
  • C Romeo, S Eaton, P A Quant, L Spitz, A Pierro. Neonatal oxidative liver metabolism: effects of hydrogen peroxide, a putative mediator of septic damage. Journal of pediatric surgery. 1999 Jul; 34(7):1107-11. doi: 10.1016/s0022-3468(99)90577-8. [PMID: 10442601]
  • M Zamparelli, S Eaton, P A Quant, A McEwan, L Spitz, A Pierro. Analgesic doses of fentanyl impair oxidative metabolism of neonatal hepatocytes. Journal of pediatric surgery. 1999 Feb; 34(2):260-3. doi: 10.1016/s0022-3468(99)90186-0. [PMID: 10052800]
  • P Bonora, I Principi, A Hochkoeppler, R Borghese, D Zannoni. The respiratory chain of the halophilic anoxygenic purple bacterium Rhodospirillum sodomense. Archives of microbiology. 1998 Nov; 170(6):435-41. doi: 10.1007/s002030050664. [PMID: 9799287]
  • H Myllykallio, F Drepper, P Mathis, F Daldal. Membrane-anchored cytochrome cy mediated microsecond time range electron transfer from the cytochrome bc1 complex to the reaction center in Rhodobacter capsulatus. Biochemistry. 1998 Apr; 37(16):5501-10. doi: 10.1021/bi973123d. [PMID: 9548933]
  • G Moschettini, A Hochkoeppler, B Monti, B Benelli, D Zannoni. The electron transport system of the halophilic purple nonsulfur bacterium Rhodospirillum salinarum. 1. A functional and thermodynamic analysis of the respiratory chain in aerobically and photosynthetically grown cells. Archives of microbiology. 1997 Oct; 168(4):302-9. doi: 10.1007/s002030050503. [PMID: 9297468]
  • F Buttgereit, M D Brand. A hierarchy of ATP-consuming processes in mammalian cells. The Biochemical journal. 1995 Nov; 312 ( Pt 1)(?):163-7. doi: 10.1042/bj3120163. [PMID: 7492307]
  • C W Van den Bergen, A M Wagner, K Krab, A L Moore. The relationship between electron flux and the redox poise of the quinone pool in plant mitochondria. Interplay between quinol-oxidizing and quinone-reducing pathways. European journal of biochemistry. 1994 Dec; 226(3):1071-8. doi: 10.1111/j.1432-1033.1994.01071.x. [PMID: 7813462]
  • G Bechmann, H Weiss, P R Rich. Non-linear inhibition curves for tight-binding inhibitors of dimeric ubiquinol-cytochrome c oxidoreductases. Evidence for rapid inhibitor mobility. European journal of biochemistry. 1992 Sep; 208(2):315-25. doi: 10.1111/j.1432-1033.1992.tb17189.x. [PMID: 1325904]
  • P Bennoun, M Delosme, U Kück. Mitochondrial genetics of Chlamydomonas reinhardtii: resistance mutations marking the cytochrome b gene. Genetics. 1991 Feb; 127(2):335-43. doi: 10.1093/genetics/127.2.335. [PMID: 2004707]
  • S Japa, D S Beattie. Electron transfer through center o of the cytochrome b-c1 complex of yeast mitochondria involves subunit VII, the ubiquinone-binding protein. The Journal of biological chemistry. 1989 Aug; 264(24):13994-7. doi: . [PMID: 2547777]
  • Q S Zhu, S G Sprague, D S Beattie. Reduction of exogenous quinones and 2,6-dichlorophenol indophenol in cytochrome b-deficient yeast mitochondria: a differential effect on center i and center o of the cytochrome b-c1 complex. Archives of biochemistry and biophysics. 1988 Sep; 265(2):447-53. doi: 10.1016/0003-9861(88)90148-8. [PMID: 2844120]
  • B C Tripathy, J S Rieske. Antimycin-resistant alternate electron pathway to plastocyanin in bovine-heart complex III. Journal of bioenergetics and biomembranes. 1985 Jun; 17(3):141-50. doi: 10.1007/bf00751058. [PMID: 2989259]