Neryl pyrophosphate (BioDeep_00000898390)
代谢物信息卡片
Neryl pyrophosphate
化学式: C10H17O7P2-3 (311.0449)
中文名称:
谱图信息:
最多检出来源 Viridiplantae(plant) 86.36%
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)/p-3/b10-7-
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
13 个相关的代谢反应过程信息。
Reactome(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(12)
- trichome monoterpenes biosynthesis:
neryl diphosphate ⟶ α-phellandrene + diphosphate - trichome monoterpenes biosynthesis:
neryl diphosphate ⟶ α-phellandrene + diphosphate - trichome monoterpenes biosynthesis:
neryl diphosphate ⟶ α-phellandrene + diphosphate - trichome monoterpenes biosynthesis:
neryl diphosphate ⟶ β-phellandrene + diphosphate - trichome monoterpenes biosynthesis:
neryl diphosphate ⟶ α-phellandrene + diphosphate - trichome monoterpenes biosynthesis:
neryl diphosphate ⟶ α-phellandrene + diphosphate - trichome monoterpenes biosynthesis:
neryl diphosphate ⟶ α-phellandrene + diphosphate - trichome monoterpenes biosynthesis:
neryl diphosphate ⟶ α-phellandrene + diphosphate - nerol biosynthesis:
DMAPP + IPP ⟶ diphosphate + neryl diphosphate - nerol biosynthesis:
DMAPP + IPP ⟶ diphosphate + neryl diphosphate - nerol biosynthesis:
DMAPP + IPP ⟶ diphosphate + neryl diphosphate - nerol biosynthesis:
H2O + neryl diphosphate ⟶ diphosphate + nerol
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 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 |
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文献列表
- Xuan Song, Chang Liu, Khalid H Dhiloo, Chao-Qun Yi, Tian-Tao Zhang, Yong-Jun Zhang. Functional characterization of a geranylgeranyl diphosphate synthase in the leaf beetle Monolepta hieroglyphica.
Archives of insect biochemistry and physiology.
2024 Feb; 115(2):e22088. doi:
10.1002/arch.22088. [PMID: 38349673] - Jie Zhang, Lea G Hansen, Olga Gudich, Konrad Viehrig, Lærke M M Lassen, Lars Schrübbers, Khem B Adhikari, Paulina Rubaszka, Elena Carrasquer-Alvarez, Ling Chen, Vasil D'Ambrosio, Beata Lehka, Ahmad K Haidar, Saranya Nallapareddy, Konstantina Giannakou, Marcos Laloux, Dushica Arsovska, Marcus A K Jørgensen, Leanne Jade G Chan, Mette Kristensen, Hanne B Christensen, Suresh Sudarsan, Emily A Stander, Edward Baidoo, Christopher J Petzold, Tune Wulff, Sarah E O'Connor, Vincent Courdavault, Michael K Jensen, Jay D Keasling. A microbial supply chain for production of the anti-cancer drug vinblastine.
Nature.
2022 09; 609(7926):341-347. doi:
10.1038/s41586-022-05157-3. [PMID: 36045295] - Nur Suhanawati Ashaari, Mohd Hairul Ab Rahim, Suriana Sabri, Kok Song Lai, Adelene Ai-Lian Song, Raha Abdul Rahim, Janna Ong Abdullah. Kinetic studies and homology modeling of a dual-substrate linalool/nerolidol synthase from Plectranthus amboinicus.
Scientific reports.
2021 08; 11(1):17094. doi:
10.1038/s41598-021-96524-z. [PMID: 34429465] - Marie Chantal Lemfack, Wolfgang Brandt, Katja Krüger, Alexandra Gurowietz, Jacky Djifack, Jan-Philip Jung, Marius Hopf, Heiko Noack, Björn Junker, Stephan von Reuß, Birgit Piechulla. Reaction mechanism of the farnesyl pyrophosphate C-methyltransferase towards the biosynthesis of pre-sodorifen pyrophosphate by Serratia plymuthica 4Rx13.
Scientific reports.
2021 02; 11(1):3182. doi:
10.1038/s41598-021-82521-9. [PMID: 33542330] - Min Kyoung You, Yeo Jin Lee, Ji Su Yu, Sun-Hwa Ha. The Predicted Functional Compartmentation of Rice Terpenoid Metabolism by Trans-Prenyltransferase Structural Analysis, Expression and Localization.
International journal of molecular sciences.
2020 Nov; 21(23):. doi:
10.3390/ijms21238927. [PMID: 33255547] - Codruta Ignea, Morten H Raadam, Mohammed S Motawia, Antonios M Makris, Claudia E Vickers, Sotirios C Kampranis. Orthogonal monoterpenoid biosynthesis in yeast constructed on an isomeric substrate.
Nature communications.
2019 08; 10(1):3799. doi:
10.1038/s41467-019-11290-x. [PMID: 31444322] - Xiaozhou Luo, Michael A Reiter, Leo d'Espaux, Jeff Wong, Charles M Denby, Anna Lechner, Yunfeng Zhang, Adrian T Grzybowski, Simon Harth, Weiyin Lin, Hyunsu Lee, Changhua Yu, John Shin, Kai Deng, Veronica T Benites, George Wang, Edward E K Baidoo, Yan Chen, Ishaan Dev, Christopher J Petzold, Jay D Keasling. Complete biosynthesis of cannabinoids and their unnatural analogues in yeast.
Nature.
2019 03; 567(7746):123-126. doi:
10.1038/s41586-019-0978-9. [PMID: 30814733] - Yong Min Lao, Hui Jin, Jin Zhou, Huai Jin Zhang, Xiao Shan Zhu, Zhong Hua Cai. A Novel Hydrolytic Activity of Tri-Functional Geranylgeranyl Pyrophosphate Synthase in Haematococcus pluvialis.
Plant & cell physiology.
2018 Dec; 59(12):2536-2548. doi:
10.1093/pcp/pcy173. [PMID: 30137453] - Pavel Mikulecky, Elena Andreeva, Patricia Amara, Winfried Weissenhorn, Yvain Nicolet, Pauline Macheboeuf. Human viperin catalyzes the modification of GPP and FPP potentially affecting cholesterol synthesis.
FEBS letters.
2018 01; 592(2):199-208. doi:
10.1002/1873-3468.12941. [PMID: 29251770] - Miki Tashiro, Akira Fujii, Shigeko Kawai-Noma, Kyoichi Saito, Daisuke Umeno. Directed evolution and expression tuning of geraniol synthase for efficient geraniol production in Escherichia coli.
The Journal of general and applied microbiology.
2017 Nov; 63(5):287-295. doi:
10.2323/jgam.2017.01.006. [PMID: 28954964] - Octavia Natascha Kracht, Ann-Christin Ammann, Julia Stockmann, Daniel Wibberg, Jörn Kalinowski, Markus Piotrowski, Russell Kerr, Thomas Brück, Robert Kourist. Transcriptome profiling of the Australian arid-land plant Eremophila serrulata (A.DC.) Druce (Scrophulariaceae) for the identification of monoterpene synthases.
Phytochemistry.
2017 Apr; 136(?):15-22. doi:
10.1016/j.phytochem.2017.01.016. [PMID: 28162767] - Jing Xi, Lorenzo Rossi, Xiuli Lin, De-Yu Xie. Overexpression of a synthetic insect-plant geranyl pyrophosphate synthase gene in Camelina sativa alters plant growth and terpene biosynthesis.
Planta.
2016 Jul; 244(1):215-30. doi:
10.1007/s00425-016-2504-8. [PMID: 27023458] - Xiaohui Ma, Juan Guo, Ying Ma, Baolong Jin, Zhilai Zhan, Yuan Yuan, Luqi Huang. Characterization of a monoterpene synthase from Paeonia lactiflora producing α-pinene as its single product.
Biotechnology letters.
2016 Jul; 38(7):1213-9. doi:
10.1007/s10529-016-2098-z. [PMID: 27053081] - 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] - Hiroshi Kiyota, Yukiko Okuda, Michiho Ito, Masami Yokota Hirai, Masahiko Ikeuchi. Engineering of cyanobacteria for the photosynthetic production of limonene from CO2.
Journal of biotechnology.
2014 Sep; 185(?):1-7. doi:
10.1016/j.jbiotec.2014.05.025. [PMID: 24905149] - Michael Gutensohn, Thuong T H Nguyen, Richard D McMahon, Ian Kaplan, Eran Pichersky, Natalia Dudareva. Metabolic engineering of monoterpene biosynthesis in tomato fruits via introduction of the non-canonical substrate neryl diphosphate.
Metabolic engineering.
2014 Jul; 24(?):107-16. doi:
10.1016/j.ymben.2014.05.008. [PMID: 24831707] - Chang-Qing Yang, Xiu-Ming Wu, Ju-Xin Ruan, Wen-Li Hu, Yin-Bo Mao, Xiao-Ya Chen, Ling-Jian Wang. Isolation and characterization of terpene synthases in cotton (Gossypium hirsutum).
Phytochemistry.
2013 Dec; 96(?):46-56. doi:
10.1016/j.phytochem.2013.09.009. [PMID: 24074555] - Xinzheng Huang, Yutao Xiao, Tobias G Köllner, Wanna Zhang, Junxiang Wu, Juan Wu, Yuyuan Guo, Yongjun Zhang. Identification and characterization of (E)-β-caryophyllene synthase and α/β-pinene synthase potentially involved in constitutive and herbivore-induced terpene formation in cotton.
Plant physiology and biochemistry : PPB.
2013 Dec; 73(?):302-8. doi:
10.1016/j.plaphy.2013.10.017. [PMID: 24184450] - Ravi S Singh, Rishi K Gara, Pardeep K Bhardwaj, Anish Kaachra, Sonia Malik, Ravi Kumar, Madhu Sharma, Paramvir S Ahuja, Sanjay Kumar. Expression of 3-hydroxy-3-methylglutaryl-CoA reductase, p-hydroxybenzoate-m-geranyltransferase and genes of phenylpropanoid pathway exhibits positive correlation with shikonins content in arnebia [Arnebia euchroma (Royle) Johnston].
BMC molecular biology.
2010 Nov; 11(?):88. doi:
10.1186/1471-2199-11-88. [PMID: 21092138] - Axel Schmidt, Betty Wächtler, Ulrike Temp, Trygve Krekling, Armand Séguin, Jonathan Gershenzon. A bifunctional geranyl and geranylgeranyl diphosphate synthase is involved in terpene oleoresin formation in Picea abies.
Plant physiology.
2010 Feb; 152(2):639-55. doi:
10.1104/pp.109.144691. [PMID: 19939949] - Tao-Hsin Chang, Fu-Lien Hsieh, Tzu-Ping Ko, Kuo-Hsun Teng, Po-Huang Liang, Andrew H-J Wang. Structure of a heterotetrameric geranyl pyrophosphate synthase from mint (Mentha piperita) reveals intersubunit regulation.
The Plant cell.
2010 Feb; 22(2):454-67. doi:
10.1105/tpc.109.071738. [PMID: 20139160] - Anthony L Schilmiller, Ines Schauvinhold, Matthew Larson, Richard Xu, Amanda L Charbonneau, Adam Schmidt, Curtis Wilkerson, Robert L Last, Eran Pichersky. Monoterpenes in the glandular trichomes of tomato are synthesized from a neryl diphosphate precursor rather than geranyl diphosphate.
Proceedings of the National Academy of Sciences of the United States of America.
2009 Jun; 106(26):10865-70. doi:
10.1073/pnas.0904113106. [PMID: 19487664] - Jörg Bohlmann, Jonathan Gershenzon. Old substrates for new enzymes of terpenoid biosynthesis.
Proceedings of the National Academy of Sciences of the United States of America.
2009 Jun; 106(26):10402-3. doi:
10.1073/pnas.0905226106. [PMID: 19553206] - Laura Calleros, Marina Lasa, Francisco J Rodríguez-Alvarez, María J Toro, Antonio Chiloeches. RhoA and p38 MAPK mediate apoptosis induced by cellular cholesterol depletion.
Apoptosis : an international journal on programmed cell death.
2006 Jul; 11(7):1161-73. doi:
10.1007/s10495-006-6980-3. [PMID: 16699960] - Annie P-C Chen, Sing-Yang Chang, Yu-Chung Lin, Yang-Sheng Sun, Chao-Tsen Chen, Andrew H-J Wang, Po-Huang Liang. Substrate and product specificities of cis-type undecaprenyl pyrophosphate synthase.
The Biochemical journal.
2005 Feb; 386(Pt 1):169-76. doi:
10.1042/bj20040785. [PMID: 15447632] - Ken'ichi Hagiwara, Akimori Wada, Maiko Katadae, Masayoshi Ito, Yoshikazu Ohya, Patrick J Casey, Yoshitaka Fukada. Analysis of the molecular interaction of the farnesyl moiety of transducin through the use of a photoreactive farnesyl analogue.
Biochemistry.
2004 Jan; 43(2):300-9. doi:
10.1021/bi0351514. [PMID: 14717583] - V G Ladygin. [Current state of carotenoid biosynthesis in chloroplasts of eucaryotes].
Zhurnal obshchei biologii.
2002 Jul; 63(4):299-325. doi:
. [PMID: 12298179] - Charles Burke, Rodney Croteau. Interaction with the small subunit of geranyl diphosphate synthase modifies the chain length specificity of geranylgeranyl diphosphate synthase to produce geranyl diphosphate.
The Journal of biological chemistry.
2002 Feb; 277(5):3141-9. doi:
10.1074/jbc.m105900200. [PMID: 11733504] - M L Wise, T J Savage, E Katahira, R Croteau. Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase.
The Journal of biological chemistry.
1998 Jun; 273(24):14891-9. doi:
10.1074/jbc.273.24.14891. [PMID: 9614092] - E Pichersky, E Lewinsohn, R Croteau. Purification and characterization of S-linalool synthase, an enzyme involved in the production of floral scent in Clarkia breweri.
Archives of biochemistry and biophysics.
1995 Feb; 316(2):803-7. doi:
10.1006/abbi.1995.1107. [PMID: 7864636] - R E LaFever, R Croteau. Hydride shifts in the biosynthesis of the p-menthane monoterpenes alpha-terpinene, gamma-terpinene, and beta-phellandrene.
Archives of biochemistry and biophysics.
1993 Mar; 301(2):361-6. doi:
10.1006/abbi.1993.1156. [PMID: 8460944] - T W Hallahan, R Croteau. Monoterpene biosynthesis: demonstration of a geranyl pyrophosphate:sabinene hydrate cyclase in soluble enzyme preparations from sweet marjoram (Majorana hortensis).
Archives of biochemistry and biophysics.
1988 Aug; 264(2):618-31. doi:
10.1016/0003-9861(88)90328-1. [PMID: 3401015] - C J Wheeler, R B Croteau. Direct demonstration of the isomerization component of the monoterpene cyclase reaction using a cyclopropylcarbinyl pyrophosphate substrate analog.
Proceedings of the National Academy of Sciences of the United States of America.
1987 Jul; 84(14):4856-9. doi:
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