Geranyl-PP (BioDeep_00000004295)

 

Secondary id: BioDeep_00000638324

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

化学式: C10H20O7P2 (314.068423)
中文名称: 香叶基焦磷酸铵盐, 香叶基焦磷酸
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.08%

分子结构信息

SMILES: CC(=CCCC(=CCOP(=O)(O)OP(=O)(O)O)C)C
InChI: InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+

描述信息

Geranyl diphosphate is the precursor of monoterpenes, a large family of natural occurring C10 compounds predominately found in plants and animals. Geranyl diphosphate is regarded as a key intermediate in the steroid, isoprene and terpene biosynthesis pathways and is used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids. (wikipedia). In humans, geranyl diphosphate synthase (GPPS) catalyzes the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl diphosphate. Animals produce IPP through the mevalonate (MVA) pathway. Isoprenoid compounds have been implicated in several human disease states including coronary heart disease, blindness, infectious hepatitis and cancer.; ; Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia; Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids.
Geranyl diphosphate is the precursor of monoterpenes, a large family of natural occurring C10 compounds predominately found in plants and animals. Geranyl diphosphate is regarded as a key intermediate in the steroid, isoprene and terpene biosynthesis pathways and is used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids. (wikipedia). In humans, geranyl diphosphate synthase (GPPS) catalyzes the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl diphosphate. Animals produce IPP through the mevalonate (MVA) pathway. Isoprenoid compounds have been implicated in several human disease states including coronary heart disease, blindness, infectious hepatitis and cancer. Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia.

同义名列表

26 个代谢物同义名

[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid; [(2E)-3,7-dimethylocta-2,6-dienyl] phosphono hydrogen phosphate; (2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate; P-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]diphosphoric acid; trans-Polyisopentenyldiphosphoric acid; Polyisopentenylpyrophosphoric acid; GERANYL PYROPHOSPHATE AMMONIUM 200; trans-Polyisopentenyldiphosphate; Polyisopentenyldiphosphoric acid; Polyisopentenylpyrophosphate; Polyprenyl diphosphoric acid; Geranyl pyrophosphoric acid; trans-Geranyl pyrophosphate; Polyisopentenyldiphosphate; Geranyl pyrophosphic acid; Monoterpenyl diphosphate; Polyprenyl diphosphate; Geranyl-pyrophosphate; Geranyl pyrophosphate; Geranyl-diphosphate; Geranyl diphosphate; Neryl diphosphate; trans-geranyl-PP; FT-0626677; Geranyl-PP; Geranyl diphosphate(Geranyl-PP)



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(2)

PlantCyc(0)

代谢反应

444 个相关的代谢反应过程信息。

Reactome(72)

BioCyc(5)

WikiPathways(5)

Plant Reactome(298)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(63)

PharmGKB(0)

55 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

  • Chen Dong, Zhiwen Wang, Lili Qin, Chen Zhang, Longyun Cao, Haifeng Li, Xintian Ma. Overexpression of Geranyl Diphosphate Synthase 1 (NnGGPPS1) From Nelumbo nucifera Enhances Carotenoid and Chlorophyll Content and Biomass. Gene. 2023 Jul; ?(?):147645. doi: 10.1016/j.gene.2023.147645. [PMID: 37453723]
  • Maria O Taratynova, Ekaterina E Tikhonova, Iuliia M Fedyaeva, Dmitry A Dementev, Tigran V Yuzbashev, Andrey I Solovyev, Sergey P Sineoky, Evgeniya Y Yuzbasheva. Boosting Geranyl Diphosphate Synthesis for Linalool Production in Engineered Yarrowia lipolytica. Applied biochemistry and biotechnology. 2023 Jul; ?(?):. doi: 10.1007/s12010-023-04581-z. [PMID: 37392322]
  • Shuyan Song, Ruitao Jin, Yufan Chen, Sitong He, Kui Li, Qian Tang, Qi Wang, Linjuan Wang, Mengjuan Kong, Natalia Dudareva, Brian J Smith, Fei Zhou, Shan Lu. The functional evolution of architecturally different plant geranyl diphosphate synthases from geranylgeranyl diphosphate synthase. The Plant cell. 2023 Mar; ?(?):. doi: 10.1093/plcell/koad083. [PMID: 36929908]
  • Bin Liu, Qinghua Liu, Zhichun Zhou, Hengfu Yin, Yini Xie. Overexpression of geranyl diphosphate synthase (PmGPPS1) boosts monoterpene and diterpene production involved in the response to pine wood nematode invasion. Tree physiology. 2022 02; 42(2):411-424. doi: 10.1093/treephys/tpab103. [PMID: 34378055]
  • Joy M Blain, Dakota L Grote, Sydney M Watkins, Gashaw M Goshu, Chanté Muller, James L Gorman, Gina Ranieri, Richard L Walter, Heike Hofstetter, James R Horn, Timothy J Hagen. Structural and biophysical characterization of the Burkholderia pseudomallei IspF inhibitor L-tryptophan hydroxamate. Bioorganic & medicinal chemistry letters. 2021 09; 48(?):128273. doi: 10.1016/j.bmcl.2021.128273. [PMID: 34298132]
  • Matthew E Bergman, Mridula Bhardwaj, Michael A Phillips. Cytosolic geraniol and citronellol biosynthesis require a Nudix hydrolase in rose-scented geranium (Pelargonium graveolens). The Plant journal : for cell and molecular biology. 2021 07; 107(2):493-510. doi: 10.1111/tpj.15304. [PMID: 33949016]
  • Simon Dusséaux, William Thomas Wajn, Yixuan Liu, Codruta Ignea, Sotirios C Kampranis. Transforming yeast peroxisomes into microfactories for the efficient production of high-value isoprenoids. Proceedings of the National Academy of Sciences of the United States of America. 2020 12; 117(50):31789-31799. doi: 10.1073/pnas.2013968117. [PMID: 33268495]
  • Xun Wang, Jing Wu, Jiaming Chen, Longjie Xiao, Yu Zhang, Fei Wang, Xun Li. Efficient Biosynthesis of R-(-)-Linalool through Adjusting the Expression Strategy and Increasing GPP Supply in Escherichia coli. Journal of agricultural and food chemistry. 2020 Aug; 68(31):8381-8390. doi: 10.1021/acs.jafc.0c03664. [PMID: 32657129]
  • Gal Hivert, Rachel Davidovich-Rikanati, Einat Bar, Yaron Sitrit, Arthur Schaffer, Natalia Dudareva, Efraim Lewinsohn. Prenyltransferases catalyzing geranyldiphosphate formation in tomato fruit. Plant science : an international journal of experimental plant biology. 2020 Jul; 296(?):110504. doi: 10.1016/j.plantsci.2020.110504. [PMID: 32540020]
  • Michele Fabris, Jestin George, Unnikrishnan Kuzhiumparambil, Caitlin A Lawson, Ana Cristina Jaramillo-Madrid, Raffaela M Abbriano, Claudia E Vickers, Peter Ralph. Extrachromosomal Genetic Engineering of the Marine Diatom Phaeodactylum tricornutum Enables the Heterologous Production of Monoterpenoids. ACS synthetic biology. 2020 03; 9(3):598-612. doi: 10.1021/acssynbio.9b00455. [PMID: 32032487]
  • Ayelign M Adal, Soheil S Mahmoud. Short-chain isoprenyl diphosphate synthases of lavender (Lavandula). Plant molecular biology. 2020 Mar; 102(4-5):517-535. doi: 10.1007/s11103-020-00962-8. [PMID: 31927660]
  • Codruta Ignea, Marianna Pontini, Mohammed S Motawia, Massimo E Maffei, Antonios M Makris, Sotirios C Kampranis. Synthesis of 11-carbon terpenoids in yeast using protein and metabolic engineering. Nature chemical biology. 2018 12; 14(12):1090-1098. doi: 10.1038/s41589-018-0166-5. [PMID: 30429605]
  • Zhuoheng Zhong, Wei Zhu, Shengzhi Liu, Qijie Guan, Xi Chen, Wei Huang, Tantan Wang, Bingxian Yang, Jingkui Tian. Molecular Characterization of a Geranyl Diphosphate-Specific Prenyltransferase Catalyzing Stilbenoid Prenylation from Morus alba. Plant & cell physiology. 2018 Nov; 59(11):2214-2227. doi: 10.1093/pcp/pcy138. [PMID: 30020500]
  • Lixia Yang, Liangzhen Jiang, Wei Li, Yun Yang, Guolin Zhang, Yinggang Luo. A homomeric geranyl diphosphate synthase-encoding gene from Camptotheca acuminata and its combinatorial optimization for production of geraniol in Escherichia coli. Journal of industrial microbiology & biotechnology. 2017 Oct; 44(10):1431-1441. doi: 10.1007/s10295-017-1967-3. [PMID: 28695386]
  • Vaishnavi Amarr Reddy, Qian Wang, Niha Dhar, Nadimuthu Kumar, Prasanna Nori Venkatesh, Chakravarthy Rajan, Deepa Panicker, Vishweshwaran Sridhar, Hui-Zhu Mao, Rajani Sarojam. Spearmint R2R3-MYB transcription factor MsMYB negatively regulates monoterpene production and suppresses the expression of geranyl diphosphate synthase large subunit (MsGPPS.LSU). Plant biotechnology journal. 2017 Sep; 15(9):1105-1119. doi: 10.1111/pbi.12701. [PMID: 28160379]
  • Benjamin R Morehouse, Ramasamy P Kumar, Jason O Matos, Sarah Naomi Olsen, Sonya Entova, Daniel D Oprian. Functional and Structural Characterization of a (+)-Limonene Synthase from Citrus sinensis. Biochemistry. 2017 03; 56(12):1706-1715. doi: 10.1021/acs.biochem.7b00143. [PMID: 28272875]
  • Li-Chan Tu, Yi-Feng Zhang, Ping Su, Tian-Yuan Hu, Yu-Ru Tong, Hong-Yu Guan, Yu-Jun Zhao, Xia-Nan Zhang, Yuan Yuan, Wei Gao, Lu-Qi Huang. [Cloning and protein expression analysis of geranyl diphosphate synthase genes in Tripterygium wilfordii]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 Jan; 42(2):220-225. doi: 10.19540/j.cnki.cjcmm.20161222.042. [PMID: 28948723]
  • Fei Chen, Wei Li, Liangzhen Jiang, Xiang Pu, Yun Yang, Guolin Zhang, Yinggang Luo. Functional characterization of a geraniol synthase-encoding gene from Camptotheca acuminata and its application in production of geraniol in Escherichia coli. Journal of industrial microbiology & biotechnology. 2016 09; 43(9):1281-92. doi: 10.1007/s10295-016-1802-2. [PMID: 27349769]
  • Yu Deng, Mingxue Sun, Sha Xu, Jingwen Zhou. Enhanced (S)-linalool production by fusion expression of farnesyl diphosphate synthase and linalool synthase in Saccharomyces cerevisiae. Journal of applied microbiology. 2016 Jul; 121(1):187-95. doi: 10.1111/jam.13105. [PMID: 26909774]
  • 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]
  • Nathalie Gatto, Abith Vattekkatte, Tobias Köllner, Jörg Degenhardt, Jonathan Gershenzon, Wilhelm Boland. Isotope sensitive branching and kinetic isotope effects to analyse multiproduct terpenoid synthases from Zea mays. Chemical communications (Cambridge, England). 2015 Mar; 51(18):3797-800. doi: 10.1039/c4cc10395e. [PMID: 25658388]
  • Ryosuke Munakata, Tsuyoshi Inoue, Takao Koeduka, Fazeelat Karamat, Alexandre Olry, Akifumi Sugiyama, Kojiro Takanashi, Audray Dugrand, Yann Froelicher, Ryo Tanaka, Yoshihiro Uto, Hitoshi Hori, Jun-Ichi Azuma, Alain Hehn, Frédéric Bourgaud, Kazufumi Yazaki. Molecular cloning and characterization of a geranyl diphosphate-specific aromatic prenyltransferase from lemon. Plant physiology. 2014 Sep; 166(1):80-90. doi: 10.1104/pp.114.246892. [PMID: 25077796]
  • Naoko Sato-Masumoto, Michiho Ito. Two types of alcohol dehydrogenase from Perilla can form citral and perillaldehyde. Phytochemistry. 2014 Aug; 104(?):12-20. doi: 10.1016/j.phytochem.2014.04.019. [PMID: 24864017]
  • Avanish Rai, Shachi S Smita, Anup Kumar Singh, Karuna Shanker, Dinesh A Nagegowda. Heteromeric and homomeric geranyl diphosphate synthases from Catharanthus roseus and their role in monoterpene indole alkaloid biosynthesis. Molecular plant. 2013 Sep; 6(5):1531-49. doi: 10.1093/mp/sst058. [PMID: 23543438]
  • Michael Gutensohn, Irina Orlova, Thuong T H Nguyen, Rachel Davidovich-Rikanati, Mario G Ferruzzi, Yaron Sitrit, Efraim Lewinsohn, Eran Pichersky, Natalia Dudareva. Cytosolic monoterpene biosynthesis is supported by plastid-generated geranyl diphosphate substrate in transgenic tomato fruits. The Plant journal : for cell and molecular biology. 2013 Aug; 75(3):351-63. doi: 10.1111/tpj.12212. [PMID: 23607888]
  • Eliana Gonzales-Vigil, David E Hufnagel, Jeongwoon Kim, Robert L Last, Cornelius S Barry. Evolution of TPS20-related terpene synthases influences chemical diversity in the glandular trichomes of the wild tomato relative Solanum habrochaites. The Plant journal : for cell and molecular biology. 2012 Sep; 71(6):921-35. doi: 10.1111/j.1365-313x.2012.05040.x. [PMID: 22563774]
  • Zerihun A Demissie, Monica A Cella, Lukman S Sarker, Travis J Thompson, Mark R Rheault, Soheil S Mahmoud. Cloning, functional characterization and genomic organization of 1,8-cineole synthases from Lavandula. Plant molecular biology. 2012 Jul; 79(4-5):393-411. doi: 10.1007/s11103-012-9920-3. [PMID: 22592779]
  • Alice Vezzaro, Sandra T Krause, Alberto Nonis, Angelo Ramina, Jörg Degenhardt, Benedetto Ruperti. Isolation and characterization of terpene synthases potentially involved in flavor development of ripening olive (Olea europaea) fruits. Journal of plant physiology. 2012 Jun; 169(9):908-14. doi: 10.1016/j.jplph.2012.01.021. [PMID: 22475500]
  • Mustafa Köksal, Wayne K W Chou, David E Cane, David W Christianson. Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate. Biochemistry. 2012 Apr; 51(14):3011-20. doi: 10.1021/bi201827a. [PMID: 22455514]
  • Danilo Aros, Veronica Gonzalez, Rudolf K Allemann, Carsten T Müller, Carlo Rosati, Hilary J Rogers. Volatile emissions of scented Alstroemeria genotypes are dominated by terpenes, and a myrcene synthase gene is highly expressed in scented Alstroemeria flowers. Journal of experimental botany. 2012 Apr; 63(7):2739-52. doi: 10.1093/jxb/err456. [PMID: 22268153]
  • Yimian Ma, Lichai Yuan, Bin Wu, Xian'en Li, Shilin Chen, Shanfa Lu. Genome-wide identification and characterization of novel genes involved in terpenoid biosynthesis in Salvia miltiorrhiza. Journal of experimental botany. 2012 Apr; 63(7):2809-23. doi: 10.1093/jxb/err466. [PMID: 22291132]
  • Motoyoshi Noike, Chengwei Liu, Yusuke Ono, Yoshimitsu Hamano, Tomonobu Toyomasu, Takeshi Sassa, Nobuo Kato, Tohru Dairi. An enzyme catalyzing O-prenylation of the glucose moiety of fusicoccin A, a diterpene glucoside produced by the fungus Phomopsis amygdali. Chembiochem : a European journal of chemical biology. 2012 Mar; 13(4):566-73. doi: 10.1002/cbic.201100725. [PMID: 22287087]
  • Sol A Green, Xiuyin Chen, Niels J Nieuwenhuizen, Adam J Matich, Mindy Y Wang, Barry J Bunn, Yar-Khing Yauk, Ross G Atkinson. Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis). Journal of experimental botany. 2012 Mar; 63(5):1951-67. doi: 10.1093/jxb/err393. [PMID: 22162874]
  • Raimund Nagel, Jonathan Gershenzon, Axel Schmidt. Nonradioactive assay for detecting isoprenyl diphosphate synthase activity in crude plant extracts using liquid chromatography coupled with tandem mass spectrometry. Analytical biochemistry. 2012 Mar; 422(1):33-8. doi: 10.1016/j.ab.2011.12.037. [PMID: 22266300]
  • Ryosuke Munakata, Tsuyoshi Inoue, Takao Koeduka, Kanako Sasaki, Yusuke Tsurumaru, Akifumi Sugiyama, Yoshihiro Uto, Hitoshi Hori, Jun-Ichi Azuma, Kazufumi Yazaki. Characterization of coumarin-specific prenyltransferase activities in Citrus limon peel. Bioscience, biotechnology, and biochemistry. 2012; 76(7):1389-93. doi: 10.1271/bbb.120192. [PMID: 22785469]
  • Tapan Kumar Mohanta, Andrea Occhipinti, Simon Atsbaha Zebelo, Maria Foti, Judith Fliegmann, Simone Bossi, Massimo E Maffei, Cinzia M Bertea. Ginkgo biloba responds to herbivory by activating early signaling and direct defenses. PloS one. 2012; 7(3):e32822. doi: 10.1371/journal.pone.0032822. [PMID: 22448229]
  • Tahira Fatima, Crystal L Snyder, William R Schroeder, Dustin Cram, Raju Datla, David Wishart, Randall J Weselake, Priti Krishna. Fatty acid composition of developing sea buckthorn (Hippophae rhamnoides L.) berry and the transcriptome of the mature seed. PloS one. 2012; 7(4):e34099. doi: 10.1371/journal.pone.0034099. [PMID: 22558083]
  • Adelene Ai Lian Song, Janna O Abdullah, Mohd Puad Abdullah, Norazizah Shafee, Raha A Rahim. Functional expression of an orchid fragrance gene in Lactococcus lactis. International journal of molecular sciences. 2012; 13(2):1582-1597. doi: 10.3390/ijms13021582. [PMID: 22408409]
  • Hongmei Luo, Chao Sun, Yongzhen Sun, Qiong Wu, Ying Li, Jingyuan Song, Yunyun Niu, Xianglin Cheng, Hongxi Xu, Chuyuan Li, Juyan Liu, André Steinmetz, Shilin Chen. Analysis of the transcriptome of Panax notoginseng root uncovers putative triterpene saponin-biosynthetic genes and genetic markers. BMC genomics. 2011 Dec; 12 Suppl 5(?):S5. doi: 10.1186/1471-2164-12-s5-s5. [PMID: 22369100]
  • Roberto A Barrero, Brett Chapman, Yanfang Yang, Paula Moolhuijzen, Gabriel Keeble-Gagnère, Nan Zhang, Qi Tang, Matthew I Bellgard, Deyou Qiu. De novo assembly of Euphorbia fischeriana root transcriptome identifies prostratin pathway related genes. BMC genomics. 2011 Dec; 12(?):600. doi: 10.1186/1471-2164-12-600. [PMID: 22151917]
  • Axel Schmidt, Raimund Nagel, Trygve Krekling, Erik Christiansen, Jonathan Gershenzon, Paal Krokene. Induction of isoprenyl diphosphate synthases, plant hormones and defense signalling genes correlates with traumatic resin duct formation in Norway spruce (Picea abies). Plant molecular biology. 2011 Dec; 77(6):577-90. doi: 10.1007/s11103-011-9832-7. [PMID: 22002747]
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