Guanosine 3'-diphosphate 5'-triphosphate (BioDeep_00000005544)

 

Secondary id: BioDeep_00001869397

human metabolite


代谢物信息卡片


{[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acid

化学式: C10H18N5O20P5 (682.9233278)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 63.16%

分子结构信息

SMILES: C1=NC2=C(N1C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)OP(=O)(O)OP(=O)(O)O)O)N=C(NC2=O)N
InChI: InChI=1S/C10H18N5O20P5/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(32-39(26,27)33-36(18,19)20)3(31-9)1-30-38(24,25)35-40(28,29)34-37(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H,28,29)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1

描述信息

This compound belongs to the family of Purine Ribonucleoside Triphosphates. These are purine ribobucleotides with triphosphate group linked to the ribose moiety.

同义名列表

12 个代谢物同义名

{[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acid; {hydroxy[(2R,3S,4R,5R)-4-hydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)-2-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphoryl}oxyphosphonic acid; Guanosine 5-triphosphoric acid,3-diphosphoric acid; Guanosine 3-diphosphoric acid 5-triphosphoric acid; 3-Diphosphate 5-triphosphate, guanosine; 5-Triphosphate, guanosine 3-diphosphate; Guanosine 3 diphosphate 5 triphosphate; Guanosine 3-diphosphate 5-triphosphate; Guanosine 5-triphosphate,3-diphosphate; Guanosine pentaphosphoric acid; Pentaphosphate, guanosine; Guanosine pentaphosphate



数据库引用编号

17 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(1)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

7 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

  • Danye Qiu, Esther Lange, Thomas M Haas, Isabel Prucker, Shinji Masuda, Yan L Wang, Georg Felix, Gabriel Schaaf, Henning J Jessen. Bacterial Pathogen Infection Triggers Magic Spot Nucleotide Signaling in Arabidopsis thaliana Chloroplasts through Specific RelA/SpoT Homologues. Journal of the American Chemical Society. 2023 07; 145(29):16081-16089. doi: 10.1021/jacs.3c04445. [PMID: 37437195]
  • Marwa Mehrez, Shanna Romand, Ben Field. New perspectives on the molecular mechanisms of stress signalling by the nucleotide guanosine tetraphosphate (ppGpp), an emerging regulator of photosynthesis in plants and algae. The New phytologist. 2023 02; 237(4):1086-1099. doi: 10.1111/nph.18604. [PMID: 36349398]
  • Danny K Fung, Kaihong Bai, Jin Yang, Xiaoli Xu, David M Stevenson, Daniel Amador-Noguez, Laixin Luo, Jue D Wang. Metabolic Promiscuity of an Orphan Small Alarmone Hydrolase Facilitates Bacterial Environmental Adaptation. mBio. 2022 12; 13(6):e0242222. doi: 10.1128/mbio.02422-22. [PMID: 36472432]
  • Seddik Harchouni, Samantha England, Julien Vieu, Shanna Romand, Aicha Aouane, Sylvie Citerne, Bertrand Legeret, Jean Alric, Yonghua Li-Beisson, Benoît Menand, Benjamin Field. Guanosine tetraphosphate (ppGpp) accumulation inhibits chloroplast gene expression and promotes super grana formation in the moss Physcomitrium (Physcomitrella) patens. The New phytologist. 2022 10; 236(1):86-98. doi: 10.1111/nph.18320. [PMID: 35715975]
  • Hanwen Li, Jinqiang Nian, Shuang Fang, Meng Guo, Xiahe Huang, Fengxia Zhang, Qing Wang, Jian Zhang, Jiaoteng Bai, Guojun Dong, Peiyong Xin, Xianzhi Xie, Fan Chen, Guodong Wang, Yingchun Wang, Qian Qian, Jianru Zuo, Jinfang Chu, Xiaohui Ma. Regulation of nitrogen starvation responses by the alarmone (p)ppGpp in rice. Journal of genetics and genomics = Yi chuan xue bao. 2022 05; 49(5):469-480. doi: 10.1016/j.jgg.2022.02.006. [PMID: 35189402]
  • Shanna Romand, Hela Abdelkefi, Cécile Lecampion, Mohamed Belaroussi, Melanie Dussenne, Brigitte Ksas, Sylvie Citerne, Jose Caius, Stefano D'Alessandro, Hatem Fakhfakh, Stefano Caffarri, Michel Havaux, Ben Field. A guanosine tetraphosphate (ppGpp) mediated brake on photosynthesis is required for acclimation to nitrogen limitation in Arabidopsis. eLife. 2022 02; 11(?):. doi: 10.7554/elife.75041. [PMID: 35156611]
  • Luisana Avilan, Regine Lebrun, Carine Puppo, Sylvie Citerne, Stephane Cuiné, Yonghua Li-Beisson, Benoît Menand, Ben Field, Brigitte Gontero. ppGpp influences protein protection, growth and photosynthesis in Phaeodactylum tricornutum. The New phytologist. 2021 05; 230(4):1517-1532. doi: 10.1111/nph.17286. [PMID: 33595847]
  • Sophie E Irving, Naznin R Choudhury, Rebecca M Corrigan. The stringent response and physiological roles of (pp)pGpp in bacteria. Nature reviews. Microbiology. 2021 04; 19(4):256-271. doi: 10.1038/s41579-020-00470-y. [PMID: 33149273]
  • Smitha Sivapragasam, Arpita Ghosh, Sanjay Kumar, Danté T Johnson, Anne Grove. Similar solutions to a common challenge: regulation of genes encoding Ralstonia solanacearum xanthine dehydrogenase. FEMS microbiology letters. 2021 03; 368(4):. doi: 10.1093/femsle/fnab022. [PMID: 33620442]
  • Anita Śliwińska, Marcin R Naliwajski, Agnieszka Pietrosiuk, Katarzyna Sykłowska-Baranek. In Vitro Response of Polyscias filicifolia (Araliaceae) Shoots to Elicitation with Alarmone-Diadenosine Triphosphate, Methyl Jasmonate, and Salicylic Acid. Cells. 2021 02; 10(2):. doi: 10.3390/cells10020419. [PMID: 33671225]
  • Sumire Ono, Sae Suzuki, Doshun Ito, Shota Tagawa, Takashi Shiina, Shinji Masuda. Plastidial (p)ppGpp Synthesis by the Ca2+-Dependent RelA-SpoT Homolog Regulates the Adaptation of Chloroplast Gene Expression to Darkness in Arabidopsis. Plant & cell physiology. 2021 Feb; 61(12):2077-2086. doi: 10.1093/pcp/pcaa124. [PMID: 33089303]
  • Bret N Peterson, Megan K M Young, Shukun Luo, Jeffrey Wang, Aaron T Whiteley, Joshua J Woodward, Liang Tong, Jue D Wang, Daniel A Portnoy. (p)ppGpp and c-di-AMP Homeostasis Is Controlled by CbpB in Listeria monocytogenes. mBio. 2020 08; 11(4):. doi: 10.1128/mbio.01625-20. [PMID: 32843560]
  • Jun Liu, Menghao Yu, Tiyakhon Chatnaparat, Jae Hoon Lee, Yanli Tian, Baishi Hu, Youfu Zhao. Comparative transcriptomic analysis of global gene expression mediated by (p) ppGpp reveals common regulatory networks in Pseudomonas syringae. BMC genomics. 2020 Apr; 21(1):296. doi: 10.1186/s12864-020-6701-2. [PMID: 32272893]
  • Ho-Wen Yang, Menghao Yu, Jae Hoon Lee, Tiyakhon Chatnaparat, Youfu Zhao. The stringent response regulator (p) ppGpp mediates virulence gene expression and survival in Erwinia amylovora. BMC genomics. 2020 Mar; 21(1):261. doi: 10.1186/s12864-020-6699-5. [PMID: 32228459]
  • Gang Li, Qian Zhao, Tian Luan, Yangbo Hu, Yueling Zhang, Ting Li, Chunlai Wang, Fang Xie, Wanjiang Zhang, Paul R Langford, Siguo Liu. Basal-Level Effects of (p)ppGpp in the Absence of Branched-Chain Amino Acids in Actinobacillus pleuropneumoniae. Journal of bacteriology. 2020 03; 202(8):. doi: 10.1128/jb.00640-19. [PMID: 32015147]
  • Yanan Zhang, Doron Teper, Jin Xu, Nian Wang. Stringent response regulators (p)ppGpp and DksA positively regulate virulence and host adaptation of Xanthomonas citri. Molecular plant pathology. 2019 11; 20(11):1550-1565. doi: 10.1111/mpp.12865. [PMID: 31621195]
  • Varsha Jha, Nishant A Dafale, Hemant J Purohit. Regulatory rewiring through global gene regulations by PhoB and alarmone (p)ppGpp under various stress conditions. Microbiological research. 2019 Oct; 227(?):126309. doi: 10.1016/j.micres.2019.126309. [PMID: 31421713]
  • C Colomer-Winter, A L Flores-Mireles, S Kundra, S J Hultgren, J A Lemos. (p)ppGpp and CodY Promote Enterococcus faecalis Virulence in a Murine Model of Catheter-Associated Urinary Tract Infection. mSphere. 2019 07; 4(4):. doi: 10.1128/msphere.00392-19. [PMID: 31341072]
  • Séverin Ronneau, Julien Caballero-Montes, Jérôme Coppine, Aurélie Mayard, Abel Garcia-Pino, Régis Hallez. Regulation of (p)ppGpp hydrolysis by a conserved archetypal regulatory domain. Nucleic acids research. 2019 01; 47(2):843-854. doi: 10.1093/nar/gky1201. [PMID: 30496454]
  • Clément Patacq, Nicolas Chaudet, Fabien Létisse. Absolute Quantification of ppGpp and pppGpp by Double-Spike Isotope Dilution Ion Chromatography-High-Resolution Mass Spectrometry. Analytical chemistry. 2018 09; 90(18):10715-10723. doi: 10.1021/acs.analchem.8b00829. [PMID: 30110552]
  • Jia Chen, Yanni Huang, Xiaoyan Yang, Haijuan Zhang, Zhan Li, Bo Qin, Xingguo Chen, Hongdeng Qiu. Highly sensitive and visual detection of guanosine 3'-diphosphate-5'-di(tri)phosphate (ppGpp) in bacteria based on copper ions-mediated 4-mercaptobenzoic acid modified gold nanoparticles. Analytica chimica acta. 2018 Sep; 1023(?):89-95. doi: 10.1016/j.aca.2018.02.082. [PMID: 29754611]
  • Ben Field. Green magic: regulation of the chloroplast stress response by (p)ppGpp in plants and algae. Journal of experimental botany. 2018 05; 69(11):2797-2807. doi: 10.1093/jxb/erx485. [PMID: 29281108]
  • Rina Honoki, Sumire Ono, Akira Oikawa, Kazuki Saito, Shinji Masuda. Significance of accumulation of the alarmone (p)ppGpp in chloroplasts for controlling photosynthesis and metabolite balance during nitrogen starvation in Arabidopsis. Photosynthesis research. 2018 Mar; 135(1-3):299-308. doi: 10.1007/s11120-017-0402-y. [PMID: 28536785]
  • Anna M Puszynska, Erin K O'Shea. ppGpp Controls Global Gene Expression in Light and in Darkness in S. elongatus. Cell reports. 2017 Dec; 21(11):3155-3165. doi: 10.1016/j.celrep.2017.11.067. [PMID: 29241543]
  • Justyna Boniecka, Justyna Prusińska, Grażyna B Dąbrowska, Anna Goc. Within and beyond the stringent response-RSH and (p)ppGpp in plants. Planta. 2017 Nov; 246(5):817-842. doi: 10.1007/s00425-017-2780-y. [PMID: 28948393]
  • C Colomer-Winter, A O Gaca, J A Lemos. Association of Metal Homeostasis and (p)ppGpp Regulation in the Pathophysiology of Enterococcus faecalis. Infection and immunity. 2017 07; 85(7):. doi: 10.1128/iai.00260-17. [PMID: 28483855]
  • Régis Hallez, Marie Delaby, Stefano Sanselicio, Patrick H Viollier. Hit the right spots: cell cycle control by phosphorylated guanosines in alphaproteobacteria. Nature reviews. Microbiology. 2017 03; 15(3):137-148. doi: 10.1038/nrmicro.2016.183. [PMID: 28138140]
  • Wieland Steinchen, Gert Bange. The magic dance of the alarmones (p)ppGpp. Molecular microbiology. 2016 08; 101(4):531-44. doi: 10.1111/mmi.13412. [PMID: 27149325]
  • Aanisa Nazir, Rajendran Harinarayanan. (p)ppGpp and the bacterial cell cycle. Journal of biosciences. 2016 Jun; 41(2):277-82. doi: 10.1007/s12038-016-9611-3. [PMID: 27240988]
  • Kuldeepkumar Ramnaresh Gupta, Priyanka Baloni, Shantinath S Indi, Dipankar Chatterji. Regulation of Growth, Cell Shape, Cell Division, and Gene Expression by Second Messengers (p)ppGpp and Cyclic Di-GMP in Mycobacterium smegmatis. Journal of bacteriology. 2016 May; 198(9):1414-22. doi: 10.1128/jb.00126-16. [PMID: 26903417]
  • Matteo Sugliani, Hela Abdelkefi, Hang Ke, Emmanuelle Bouveret, Christophe Robaglia, Stefano Caffarri, Ben Field. An Ancient Bacterial Signaling Pathway Regulates Chloroplast Function to Influence Growth and Development in Arabidopsis. The Plant cell. 2016 Mar; 28(3):661-79. doi: 10.1105/tpc.16.00045. [PMID: 26908759]
  • Tiyakhon Chatnaparat, Zhong Li, Schuyler S Korban, Youfu Zhao. The bacterial alarmone (p)ppGpp is required for virulence and controls cell size and survival of Pseudomonas syringae on plants. Environmental microbiology. 2015 Nov; 17(11):4253-70. doi: 10.1111/1462-2920.12744. [PMID: 25626964]
  • Wieland Steinchen, Jan S Schuhmacher, Florian Altegoer, Christopher D Fage, Vasundara Srinivasan, Uwe Linne, Mohamed A Marahiel, Gert Bange. Catalytic mechanism and allosteric regulation of an oligomeric (p)ppGpp synthetase by an alarmone. Proceedings of the National Academy of Sciences of the United States of America. 2015 Oct; 112(43):13348-53. doi: 10.1073/pnas.1505271112. [PMID: 26460002]
  • Veronica Ancona, Jae Hoon Lee, Tiyakhon Chatnaparat, Jinrok Oh, Jong-In Hong, Youfu Zhao. The bacterial alarmone (p)ppGpp activates the type III secretion system in Erwinia amylovora. Journal of bacteriology. 2015 Apr; 197(8):1433-43. doi: 10.1128/jb.02551-14. [PMID: 25666138]
  • Usheer Kanjee, Koji Ogata, Walid A Houry. Direct binding targets of the stringent response alarmone (p)ppGpp. Molecular microbiology. 2012 Sep; 85(6):1029-43. doi: 10.1111/j.1365-2958.2012.08177.x. [PMID: 22812515]
  • Julia V Bugrysheva, Henry P Godfrey, Ira Schwartz, Felipe C Cabello. Patterns and regulation of ribosomal RNA transcription in Borrelia burgdorferi. BMC microbiology. 2011 Jan; 11(?):17. doi: 10.1186/1471-2180-11-17. [PMID: 21251259]
  • Maarten Vercruysse, Maarten Fauvart, Ann Jans, Serge Beullens, Kristien Braeken, Lore Cloots, Kristof Engelen, Kathleen Marchal, Jan Michiels. Stress response regulators identified through genome-wide transcriptome analysis of the (p)ppGpp-dependent response in Rhizobium etli. Genome biology. 2011; 12(2):R17. doi: 10.1186/gb-2011-12-2-r17. [PMID: 21324192]
  • Jun Wu, Jianping Xie. Magic spot: (p) ppGpp. Journal of cellular physiology. 2009 Aug; 220(2):297-302. doi: 10.1002/jcp.21797. [PMID: 19391118]
  • Hyun-Woo Rhee, Chang-Ro Lee, Seung-Hyon Cho, Mi-Ryung Song, Michael Cashel, Hyon E Choy, Young-Jae Seok, Jong-In Hong. Selective fluorescent chemosensor for the bacterial alarmone (p)ppGpp. Journal of the American Chemical Society. 2008 Jan; 130(3):784-5. doi: 10.1021/ja0759139. [PMID: 18166051]
  • Kristien Braeken, Martine Moris, Ruth Daniels, Jos Vanderleyden, Jan Michiels. New horizons for (p)ppGpp in bacterial and plant physiology. Trends in microbiology. 2006 Jan; 14(1):45-54. doi: 10.1016/j.tim.2005.11.006. [PMID: 16343907]
  • Grazyna Dabrowska, Justyna Prusińska, Anna Goc. [Plant mechanism of an adaptive stress response homologous to bacterial stringent response]. Postepy biochemii. 2006; 52(1):94-100. doi: ". [PMID: 16869307]
  • Marc B Concepcion, David R Nelson. Expression of spoT in Borrelia burgdorferi during serum starvation. Journal of bacteriology. 2003 Jan; 185(2):444-52. doi: 10.1128/jb.185.2.444-452.2003. [PMID: 12511489]
  • Akiyo Yamada, Kouichi Tsutsumi, Shizufumi Tanimoto, Yoshihiro Ozeki. Plant RelA/SpoT homolog confers salt tolerance in Escherichia coli and Saccharomyces cerevisiae. Plant & cell physiology. 2003 Jan; 44(1):3-9. doi: 10.1093/pcp/pcg001. [PMID: 12552141]
  • E A van der Biezen, J Sun, M J Coleman, M J Bibb, J D Jones. Arabidopsis RelA/SpoT homologs implicate (p)ppGpp in plant signaling. Proceedings of the National Academy of Sciences of the United States of America. 2000 Mar; 97(7):3747-52. doi: 10.1073/pnas.97.7.3747. [PMID: 10725385]
  • D Riesenberg. A radioimmunoassay for (p)ppGpp and its application to Streptomyces hygroscopicus. Journal of basic microbiology. 1985; 25(2):127-40. doi: 10.1002/jobm.3620250209. [PMID: 4009429]
  • J Akinyanju, R J Smith. Accumulation of ppGpp and pppGpp during nitrogen deprivation of the cyanophyte Anabaena cylindrica. FEBS letters. 1979 Nov; 107(1):173-6. doi: 10.1016/0014-5793(79)80489-5. [PMID: 115718]