Isopentenyl pyrophosphate (BioDeep_00000001656)

 

Secondary id: BioDeep_00000415832

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid

化学式: C5H12O7P2 (246.0058262)
中文名称: 异戊烯焦磷酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.13%

分子结构信息

SMILES: C(O[P@](=O)(OP(=O)(O)O)O)CC(=C)C
InChI: InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)

描述信息

Isopentenyl pyrophosphate, also known as delta3-isopentenyl diphosphate or ipp, is a member of the class of compounds known as isoprenoid phosphates. Isoprenoid phosphates are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit. Thus, isopentenyl pyrophosphate is considered to be an isoprenoid lipid molecule. Isopentenyl pyrophosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Isopentenyl pyrophosphate can be found in a number of food items such as american butterfish, conch, tea leaf willow, and butternut, which makes isopentenyl pyrophosphate a potential biomarker for the consumption of these food products. Isopentenyl pyrophosphate can be found primarily in human spleen tissue. Isopentenyl pyrophosphate exists in all living species, ranging from bacteria to humans. In humans, isopentenyl pyrophosphate is involved in several metabolic pathways, some of which include ibandronate action pathway, lovastatin action pathway, fluvastatin action pathway, and pravastatin action pathway. Isopentenyl pyrophosphate is also involved in several metabolic disorders, some of which include hypercholesterolemia, hyper-igd syndrome, lysosomal acid lipase deficiency (wolman disease), and wolman disease. Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in the non-mevalonate MEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids .
Isopentenyl pyrophosphate, IPP or isopentenyl diphosphate, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from Mevalonate-5-pyrophosphate, in a reaction catalyzed by the enzyme mevalonate-5-pyrophosphate decarboxylase. (wikipedia).

同义名列表

39 个代谢物同义名

({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid; 3-Methylbut-3-enyl phosphono hydrogen phosphoric acid; 3-Methylbut-3-en-1-yl trihydrogen diphosphoric acid; Diphosphoric acid mono(3-methyl-3-butenyl) ester; 3-Methylbut-3-enyl phosphono hydrogen phosphate; 3-Methylbut-3-en-1-yl trihydrogen diphosphate; Diphosphate mono(3-methyl-3-butenyl) ester; mono(3-Methyl-3-butenyl) diphosphoric acid; Isopentenyl pyrophosphate, 4-(14)C-labeled; delta3-Methyl-3-butenyl diphosphoric acid; delta-3-Isopentenyl pyrophosphoric acid; 3-Methyl-3-butenyl pyrophosphoric acid; Δ3-methyl-3-butenyl diphosphoric acid; δ3-methyl-3-butenyl diphosphate; mono(3-Methyl-3-butenyl) diphosphate; delta3-Isopentenyl diphosphoric acid; delta3-Methyl-3-butenyl diphosphate; Δ-3-isopentenyl pyrophosphoric acid; δ-3-Isopentenyl pyrophosphat; delta-3-Isopentenyl pyrophosphate; delta-3-Isopentenyl pyrophosphat; δ3-isopentenyl diphosphate; 3-Methyl-3-butenyl pyrophosphate; Δ3-isopentenyl diphosphoric acid; Δ3-methyl-3-butenyl diphosphate; Isopentenyl pyrophosphoric acid; delta3-Isopentenyl diphosphate; Isopentenyl pyrophosphic acid; Δ-3-isopentenyl pyrophosphate; Δ3-isopentenyl diphosphate; isopentenyl pyrophosphate; Isopentenyl-diphosphate; delta(3)-Isopentenyl-PP; Isopentenyl diphosphate; Isopentenyl-PP; IPPP; IPP; IPR; Isopentenyl pyrophosphate



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(18)

BioCyc(3)

PlantCyc(0)

代谢反应

881 个相关的代谢反应过程信息。

Reactome(219)

BioCyc(15)

WikiPathways(4)

Plant Reactome(572)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(69)

PharmGKB(0)

25 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

  • Hanwen Yu, Bowen Chen, Jing Li, Nan Dong, Xiangwei Chang, Jutao Wang, Huasheng Peng, Liangping Zha, Shuangying Gui. Identification and functional characterization of two trans-isopentenyl diphosphate synthases and one squalene synthase involved in triterpenoid biosynthesis in Platycodon grandiflorus. Planta. 2023 Nov; 258(6):115. doi: 10.1007/s00425-023-04273-2. [PMID: 37943378]
  • Zarley Rebholz, Leena Shewade, Kylie Kaler, Hailey Larose, Florian Schubot, Dorothea Tholl, Alexandre V Morozov, Paul E O'Maille. Emergence of terpene chemical communication in insects: Evolutionary recruitment of isoprenoid metabolism. Protein science : a publication of the Protein Society. 2023 Mar; ?(?):e4634. doi: 10.1002/pro.4634. [PMID: 36974623]
  • Meng Xia, Yifeng Zhang, Haiyun Gao, Yuan Liu, Xiaoyi Wu, Wei Gao. [Effect of isopentenyl pyrophosphate translocation on the biosynthesis of triptolide]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2021 Jun; 37(6):2039-2049. doi: 10.13345/j.cjb.200752. [PMID: 34227293]
  • Toni Krause, Michael Reichelt, Jonathan Gershenzon, Axel Schmidt. Analysis of the isoprenoid pathway intermediates, dimethylallyl diphosphate and isopentenyl diphosphate, from crude plant extracts by liquid chromatography tandem mass spectrometry. Phytochemical analysis : PCA. 2020 Nov; 31(6):770-777. doi: 10.1002/pca.2941. [PMID: 32337807]
  • Hachemi Kadri, Taher E Taher, Qin Xu, Maria Sharif, Elizabeth Ashby, Richard T Bryan, Benjamin E Willcox, Youcef Mehellou. Aryloxy Diester Phosphonamidate Prodrugs of Phosphoantigens (ProPAgens) as Potent Activators of Vγ9/Vδ2 T-Cell Immune Responses. Journal of medicinal chemistry. 2020 10; 63(19):11258-11270. doi: 10.1021/acs.jmedchem.0c01232. [PMID: 32930595]
  • Satoshi Yamashita, Seiji Takahashi. Molecular Mechanisms of Natural Rubber Biosynthesis. Annual review of biochemistry. 2020 06; 89(?):821-851. doi: 10.1146/annurev-biochem-013118-111107. [PMID: 32228045]
  • Cuihua Liu, Min He, Zhuang Wang, Juan Xu. Integrative Analysis of Terpenoid Profiles and Hormones from Fruits of Red-Flesh Citrus Mutants and Their Wild Types. Molecules (Basel, Switzerland). 2019 Sep; 24(19):. doi: 10.3390/molecules24193456. [PMID: 31547628]
  • Geraldy L S Liman, Tyler Hulko, Hallie P Febvre, Aaron C Brachfeld, Thomas J Santangelo. A linear pathway for mevalonate production supports growth of Thermococcus kodakarensis. Extremophiles : life under extreme conditions. 2019 Mar; 23(2):229-238. doi: 10.1007/s00792-019-01076-w. [PMID: 30673855]
  • Sarada D Tetali. Terpenes and isoprenoids: a wealth of compounds for global use. Planta. 2019 Jan; 249(1):1-8. doi: 10.1007/s00425-018-3056-x. [PMID: 30467631]
  • Laura K Henry, Suzanne T Thomas, Joshua R Widhalm, Joseph H Lynch, Thomas C Davis, Sharon A Kessler, Jörg Bohlmann, Joseph P Noel, Natalia Dudareva. Contribution of isopentenyl phosphate to plant terpenoid metabolism. Nature plants. 2018 09; 4(9):721-729. doi: 10.1038/s41477-018-0220-z. [PMID: 30127411]
  • Kevin W George, Mitchell G Thompson, Joonhoon Kim, Edward E K Baidoo, George Wang, Veronica Teixeira Benites, Christopher J Petzold, Leanne Jade G Chan, Suzan Yilmaz, Petri Turhanen, Paul D Adams, Jay D Keasling, Taek Soon Lee. Integrated analysis of isopentenyl pyrophosphate (IPP) toxicity in isoprenoid-producing Escherichia coli. Metabolic engineering. 2018 05; 47(?):60-72. doi: 10.1016/j.ymben.2018.03.004. [PMID: 29530749]
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  • Hiroyuki Kajiura, Nobuaki Suzuki, Yuji Tokumoto, Takuya Yoshizawa, Shinya Takeno, Kazuhito Fujiyama, Yoshinobu Kaneko, Hiroyoshi Matsumura, Yoshihisa Nakazawa. Two Eucommia farnesyl diphosphate synthases exhibit distinct enzymatic properties leading to end product preferences. Biochimie. 2017 Aug; 139(?):95-106. doi: 10.1016/j.biochi.2017.05.001. [PMID: 28478108]
  • Barbara Castella, Joanna Kopecka, Patrizia Sciancalepore, Giorgia Mandili, Myriam Foglietta, Nico Mitro, Donatella Caruso, Francesco Novelli, Chiara Riganti, Massimo Massaia. The ATP-binding cassette transporter A1 regulates phosphoantigen release and Vγ9Vδ2 T cell activation by dendritic cells. Nature communications. 2017 06; 8(?):15663. doi: 10.1038/ncomms15663. [PMID: 28580927]
  • Chen Xu, Yingjia Yu, Li Ling, Xueni Sun, Yan Li, Gengli Duan. Novel strategy for the facile enrichment of isopentenyl pyrophosphate in rat plasma via Ti4+ -immobilized polydopamine@Fe3 O4 core-shell microspheres. Journal of separation science. 2017 May; 40(10):2278-2285. doi: 10.1002/jssc.201600860. [PMID: 28371337]
  • Bok-Kyu Shin, Mihyang Kim, Jaehong Han. Exceptionally high percentage of IPP synthesis by Ginkgo biloba IspH is mainly due to Phe residue in the active site. Phytochemistry. 2017 Apr; 136(?):9-14. doi: 10.1016/j.phytochem.2017.01.012. [PMID: 28139297]
  • Julie E Chaves, Paloma Rueda Romero, Henning Kirst, Anastasios Melis. Role of isopentenyl-diphosphate isomerase in heterologous cyanobacterial (Synechocystis) isoprene production. Photosynthesis research. 2016 Dec; 130(1-3):517-527. doi: 10.1007/s11120-016-0293-3. [PMID: 27412351]
  • Ilya Pankratov, Ryan McQuinn, Jochanan Schwartz, Einat Bar, Zhangjun Fei, Efraim Lewinsohn, Dani Zamir, James J Giovannoni, Joseph Hirschberg. Fruit carotenoid-deficient mutants in tomato reveal a function of the plastidial isopentenyl diphosphate isomerase (IDI1) in carotenoid biosynthesis. The Plant journal : for cell and molecular biology. 2016 10; 88(1):82-94. doi: 10.1111/tpj.13232. [PMID: 27288653]
  • Mei Xia, Danny C Hesser, Prithwiraj De, Isaac G Sakala, Charles T Spencer, Jay S Kirkwood, Getahun Abate, Delphi Chatterjee, Karen M Dobos, Daniel F Hoft. A Subset of Protective γ9δ2 T Cells Is Activated by Novel Mycobacterial Glycolipid Components. Infection and immunity. 2016 09; 84(9):2449-62. doi: 10.1128/iai.01322-15. [PMID: 27297390]
  • Kariona A Grabińska, Eon Joo Park, William C Sessa. cis-Prenyltransferase: New Insights into Protein Glycosylation, Rubber Synthesis, and Human Diseases. The Journal of biological chemistry. 2016 08; 291(35):18582-90. doi: 10.1074/jbc.r116.739490. [PMID: 27402831]
  • Lemeng Dong, Esmer Jongedijk, Harro Bouwmeester, Alexander Van Der Krol. Monoterpene biosynthesis potential of plant subcellular compartments. The New phytologist. 2016 Jan; 209(2):679-90. doi: 10.1111/nph.13629. [PMID: 26356766]
  • Aparajita Banerjee, Alyssa L Preiser, Thomas D Sharkey. Engineering of Recombinant Poplar Deoxy-D-Xylulose-5-Phosphate Synthase (PtDXS) by Site-Directed Mutagenesis Improves Its Activity. PloS one. 2016; 11(8):e0161534. doi: 10.1371/journal.pone.0161534. [PMID: 27548482]
  • Xianan Zhang, Hongyu Guan, Zhubo Dai, Juan Guo, Ye Shen, Guanghong Cui, Wei Gao, Luqi Huang. Functional Analysis of the Isopentenyl Diphosphate Isomerase of Salvia miltiorrhiza via Color Complementation and RNA Interference. Molecules (Basel, Switzerland). 2015 Nov; 20(11):20206-18. doi: 10.3390/molecules201119689. [PMID: 26569204]
  • Laura K Henry, Michael Gutensohn, Suzanne T Thomas, Joseph P Noel, Natalia Dudareva. Orthologs of the archaeal isopentenyl phosphate kinase regulate terpenoid production in plants. Proceedings of the National Academy of Sciences of the United States of America. 2015 Aug; 112(32):10050-5. doi: 10.1073/pnas.1504798112. [PMID: 26216978]
  • Shakeel J Abbassi, Rishi K Vishwakarma, Parth Patel, Uma Kumari, Bashir M Khan. Bacopa monniera recombinant mevalonate diphosphate decarboxylase: Biochemical characterization. International journal of biological macromolecules. 2015 Aug; 79(?):661-8. doi: 10.1016/j.ijbiomac.2015.05.041. [PMID: 26027607]
  • Xiao-Mi Wang, Bo Yang, Cheng-Gang Ren, Hong-Wei Wang, Jin-Yan Wang, Chuan-Chao Dai. Involvement of abscisic acid and salicylic acid in signal cascade regulating bacterial endophyte-induced volatile oil biosynthesis in plantlets of Atractylodes lancea. Physiologia plantarum. 2015 Jan; 153(1):30-42. doi: 10.1111/ppl.12236. [PMID: 24862990]
  • Nazia Nisar, Li Li, Shan Lu, Nay Chi Khin, Barry J Pogson. Carotenoid metabolism in plants. Molecular plant. 2015 Jan; 8(1):68-82. doi: 10.1016/j.molp.2014.12.007. [PMID: 25578273]
  • Cinzia Formighieri, Anastasios Melis. Carbon partitioning to the terpenoid biosynthetic pathway enables heterologous β-phellandrene production in Escherichia coli cultures. Archives of microbiology. 2014 Dec; 196(12):853-61. doi: 10.1007/s00203-014-1024-9. [PMID: 25116411]
  • Sergiy G Krasutsky, Marek Urbansky, Chad E Davis, Christian Lherbet, Robert M Coates, C Dale Poulter. Synthesis of methylerythritol phosphate analogues and their evaluation as alternate substrates for IspDF and IspE from Agrobacterium tumefaciens. The Journal of organic chemistry. 2014 Oct; 79(19):9170-8. doi: 10.1021/jo501529k. [PMID: 25184438]
  • A Banerjee, T D Sharkey. Methylerythritol 4-phosphate (MEP) pathway metabolic regulation. Natural product reports. 2014 Aug; 31(8):1043-55. doi: 10.1039/c3np70124g. [PMID: 24921065]
  • Hao Zhang, Zheng-Xi Li. A type-III insect geranylgeranyl diphosphate synthase with a novel catalytic property. Protein and peptide letters. 2014 Jul; 21(7):615-23. doi: 10.2174/0929866521666140214123942. [PMID: 24527738]
  • Bhawna Saxena, Mayavan Subramaniyan, Karan Malhotra, Neel Sarovar Bhavesh, Shobha Devi Potlakayala, Shashi Kumar. Metabolic engineering of chloroplasts for artemisinic acid biosynthesis and impact on plant growth. Journal of biosciences. 2014 Mar; 39(1):33-41. doi: 10.1007/s12038-013-9402-z. [PMID: 24499788]
  • Changfang Zhou, Ziru Li, Amy E Wiberley-Bradford, Sean E Weise, Thomas D Sharkey. Isopentenyl diphosphate and dimethylallyl diphosphate/isopentenyl diphosphate ratio measured with recombinant isopentenyl diphosphate isomerase and isoprene synthase. Analytical biochemistry. 2013 Sep; 440(2):130-6. doi: 10.1016/j.ab.2013.05.028. [PMID: 23747531]
  • Aparajita Banerjee, Yan Wu, Rahul Banerjee, Yue Li, Honggao Yan, Thomas D Sharkey. Feedback inhibition of deoxy-D-xylulose-5-phosphate synthase regulates the methylerythritol 4-phosphate pathway. The Journal of biological chemistry. 2013 Jun; 288(23):16926-16936. doi: 10.1074/jbc.m113.464636. [PMID: 23612965]
  • Nobuaki Suzuki, Hirotaka Uefuji, Takashi Nishikawa, Yukio Mukai, Atsushi Yamashita, Masahira Hattori, Naotake Ogasawara, Takeshi Bamba, Ei-ichiro Fukusaki, Akio Kobayashi, Yoshiyuki Ogata, Nozomu Sakurai, Hideyuki Suzuki, Daisuke Shibata, Yoshihisa Nakazawa. Construction and analysis of EST libraries of the trans-polyisoprene producing plant, Eucommia ulmoides Oliver. Planta. 2012 Nov; 236(5):1405-17. doi: 10.1007/s00425-012-1679-x. [PMID: 22729820]
  • Grégory Guirimand, Anthony Guihur, Michael A Phillips, Audrey Oudin, Gaëlle Glévarec, Samira Mahroug, Céline Melin, Nicolas Papon, Marc Clastre, Nathalie Giglioli-Guivarc'h, Benoit St-Pierre, Manuel Rodríguez-Concepción, Vincent Burlat, Vincent Courdavault. Triple subcellular targeting of isopentenyl diphosphate isomerases encoded by a single gene. Plant signaling & behavior. 2012 Nov; 7(11):1495-7. doi: 10.4161/psb.21892. [PMID: 22951398]
  • Kuo-Hsun Teng, Po-Huang Liang. Undecaprenyl diphosphate synthase, a cis-prenyltransferase synthesizing lipid carrier for bacterial cell wall biosynthesis. Molecular membrane biology. 2012 Nov; 29(7):267-73. doi: 10.3109/09687688.2012.674162. [PMID: 22471620]
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