isopentenyl adenosine (BioDeep_00000003153)

 

Secondary id: BioDeep_00000398276, BioDeep_00000400185, BioDeep_00000408658, BioDeep_00001893343

natural product human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxolane-3,4-diol

化学式: C15H21N5O4 (335.15934660000005)
中文名称: 利波腺苷, N6-异戊烯基腺苷
谱图信息: 最多检出来源 Viridiplantae(plant) 0.05%

分子结构信息

SMILES: CC(=CCNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O)C
InChI: InChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)

描述信息

Riboprine, also known as isopentenyladenosine or ipa, is a member of the class of compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Riboprine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Riboprine can be found in a number of food items such as peppermint, chinese mustard, custard apple, and green bean, which makes riboprine a potential biomarker for the consumption of these food products.
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
D006133 - Growth Substances > D010937 - Plant Growth Regulators > D003583 - Cytokinins
Acquisition and generation of the data is financially supported in part by CREST/JST.
Same as: D05726
N6-Isopentenyladenosine (Riboprine), an RNA modification found in cytokinins, which regulate plant growth/differentiation, and a subset of tRNAs, where it improves the efficiency and accuracy of translation. N6-Isopentenyladenosine, an end product of the mevalonate pathway, is an autophagy inhibitor with an interesting anti-melanoma activity[1][2][3].

同义名列表

45 个代谢物同义名

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxolane-3,4-diol; 6-(3-Methyl-2-butenylamino)-9-beta-D-ribofuranosylpurine; 6-(3-Methyl-2-butenylamino)-beta,D-ribofuranosylpurine; 6-(3-Methyl-2-butenylamino)-9-beta-ribofuranosylpurine; 6-(3-Methyl-2-butenylamino)-9-β-D-ribofuranosylpurine; 6-(3-Methyl-2-butenylamino)-β,D-ribofuranosylpurine; 6-(3-Methyl-2-butenylamino)-9-β-ribofuranosylpurine; 6-(gamma,gamma-Dimethylallylamino)purine riboside; N-6-(delta-2-Isopentenyl)adenosine hemihydrate; 6-(3-Methyl-2-butenylamino)purine riboside; 6-(g,g-Dimethylallylamino)purine riboside; 6-(Γ,γ-dimethylallylamino)purine riboside; N6-(delta2-Isopentenyl)adenine riboside; N6-(gamma,gamma-Dimethylallyl)adenosine; N(6)-(delta(2)-Isopentenyl)adenosine; N6-(Δ2-Isopentenyl)adenine riboside; N(6)-(3-Methyl-2-butenyl)adenosine; N-(3-Methyl-2-buten-1-yl)adenosine; N-6-(delta-2-Isopentenyl)adenosine; N6-(delta2-Isopentenyl)adenosine; N6-(3-Methyl-2-butenyl)adenosine; N-(3-Methyl-2-butenyl)adenosine; N-(3-Methylbut-2-enyl)adenosine; N6-(γ,γ-Dimethylallyl)adenosine; N(6)-(2-Isopentenyl)adenosine; Isopentenyladenosine riboside; N6-(Δ2-Isopentenyl)adenosine; N6-(Dimethylallyl)adenosine; N6-(2-Isopentenyl)adenosine; Isopentenyladenine riboside; 6-(2-Isopentenyl)adenosine; N6-2-Isopentenyladenosine; N6-Isopentenyladenosine; N-Isopentenyladenosine; isopentenyl adenosine; Isopentenyladenosine; Riboprinum; Riboprine; Riboprina; 2-IPA; 2iPR; 2IPA; IPA; i6a; Isopentenyl adenosine



数据库引用编号

36 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

125 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(6)

INOH(0)

PlantCyc(116)

COVID-19 Disease Map(0)

PathBank(1)

  • Cytokinins Degradation: FAD + Hydrogen Ion + N6-dimethylallyladenine + Water ⟶ 3-Methyl-2-butenal + Adenine + FADH

PharmGKB(0)

13 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

  • Yuanyuan Li, Hongling Zhou, Shasha Chen, Yinan Li, Yuyang Guo, Xiaoqian Chen, Sheng Wang, Li Wang, Youfang Gan, Shusheng Zhang, Ya Ying Zheng, Jia Sheng, Zhipeng Zhou, Rui Wang. Bioorthogonal labeling and profiling of N6-isopentenyladenosine (i6A) modified RNA. Nucleic acids research. 2024 Apr; 52(6):2808-2820. doi: 10.1093/nar/gkae150. [PMID: 38426933]
  • Rakesh K Upadhyay, Vaclav Motyka, Eva Pokorna, Petre I Dobrev, Jozef Lacek, Jonathan Shao, Kim S Lewers, Autar K Mattoo. Comprehensive profiling of endogenous phytohormones and expression analysis of 1-aminocyclopropane-1-carboxylic acid synthase gene family during fruit development and ripening in octoploid strawberry (Fragaria× ananassa). Plant physiology and biochemistry : PPB. 2023 Jan; 196(?):186-196. doi: 10.1016/j.plaphy.2023.01.031. [PMID: 36724703]
  • Muhammad Saqlain Zaheer, Hafiz Haider Ali, Kehinde O Erinle, Shabir Hussain Wani, Okon Godwin Okon, Muhammad Azhar Nadeem, Muhammad Nawaz, Muhammad Adnan Bodlah, Muhammad Mohsin Waqas, Javaid Iqbal, Ali Raza. Inoculation of Azospirillum brasilense and exogenous application of trans-zeatin riboside alleviates arsenic induced physiological damages in wheat (Triticum aestivum). Environmental science and pollution research international. 2022 May; 29(23):33909-33919. doi: 10.1007/s11356-021-18106-w. [PMID: 35031990]
  • Shaohuan Li, Muhammad Mobeen Tahir, Tong Wu, Lingling Xie, Xiaoyun Zhang, Jiangping Mao, Anam Ayyoub, Libo Xing, Dong Zhang, Yun Shao. Transcriptome Analysis Reveals Multiple Genes and Complex Hormonal-Mediated Interactions with PEG during Adventitious Root Formation in Apple. International journal of molecular sciences. 2022 Jan; 23(2):. doi: 10.3390/ijms23020976. [PMID: 35055162]
  • Juanjuan Ma, Lingling Xie, Qian Zhao, Yiting Sun, Dong Zhang. Cyclanilide Induces Lateral Bud Outgrowth by Modulating Cytokinin Biosynthesis and Signalling Pathways in Apple Identified via Transcriptome Analysis. International journal of molecular sciences. 2022 Jan; 23(2):. doi: 10.3390/ijms23020581. [PMID: 35054767]
  • Sergey N Lomin, Ekaterina M Savelieva, Dmitry V Arkhipov, Pavel P Pashkovskiy, Yulia A Myakushina, Alexander Heyl, Georgy A Romanov. Cytokinin Perception in Ancient Plants beyond Angiospermae. International journal of molecular sciences. 2021 Dec; 22(23):. doi: 10.3390/ijms222313077. [PMID: 34884882]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Hou-Ping Cheng, Xiao-Hui Yang, Ling Lan, Li-Jun Xie, Chuan Chen, Cuimei Liu, Jinfang Chu, Zhi-Yan Li, Li Liu, Tian-Qi Zhang, Du-Qiang Luo, Liang Cheng. Chemical Deprenylation of N6 -Isopentenyladenosine (i6 A) RNA. Angewandte Chemie (International ed. in English). 2020 06; 59(26):10645-10650. doi: 10.1002/anie.202003360. [PMID: 32198805]
  • Minqiang Tang, Chaobo Tong, Longbin Liang, Caifu Du, Jixian Zhao, Langtao Xiao, Jianhua Tong, Xianglai Dai, Mmu Helal, Wendong Dai, Yang Xiang. A recessive high-density pod mutant resource of Brassica napus. Plant science : an international journal of experimental plant biology. 2020 Apr; 293(?):110411. doi: 10.1016/j.plantsci.2020.110411. [PMID: 32081260]
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  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
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  • Toshiki Takenouchi, Fan-Yan Wei, Hisato Suzuki, Tomoko Uehara, Takao Takahashi, Yasushi Okazaki, Kenjiro Kosaki, Kazuhito Tomizawa. Noninvasive diagnosis of TRIT1-related mitochondrial disorder by measuring i6 A37 and ms2 i6 A37 modifications in tRNAs from blood and urine samples. American journal of medical genetics. Part A. 2019 08; 179(8):1609-1614. doi: 10.1002/ajmg.a.61211. [PMID: 31140736]
  • Jia Gao, Jianguo Shi, Shuting Dong, Peng Liu, Bin Zhao, Jiwang Zhang. Grain development and endogenous hormones in summer maize (Zea mays L.) submitted to different light conditions. International journal of biometeorology. 2018 Dec; 62(12):2131-2138. doi: 10.1007/s00484-018-1613-4. [PMID: 30244320]
  • Stanislav Yu Veselov, Leila N Timergalina, Guzel R Akhiyarova, Guzel R Kudoyarova, Alla V Korobova, Igor Ivanov, Tatiana N Arkhipova, Els Prinsen. Study of cytokinin transport from shoots to roots of wheat plants is informed by a novel method of differential localization of free cytokinin bases or their ribosylated forms by means of their specific fixation. Protoplasma. 2018 Sep; 255(5):1581-1594. doi: 10.1007/s00709-018-1248-7. [PMID: 29637285]
  • Christoph Brütting, Cristina Maria Crava, Martin Schäfer, Meredith C Schuman, Stefan Meldau, Nora Adam, Ian T Baldwin. Cytokinin transfer by a free-living mirid to Nicotiana attenuata recapitulates a strategy of endophytic insects. eLife. 2018 07; 7(?):. doi: 10.7554/elife.36268. [PMID: 30014847]
  • Karolina Kubiasová, Václav Mik, Jaroslav Nisler, Martin Hönig, Alexandra Husičková, Lukáš Spíchal, Zuzana Pěkná, Olga Šamajová, Karel Doležal, Ondřej Plíhal, Eva Benková, Miroslav Strnad, Lucie Plíhalová. Design, synthesis and perception of fluorescently labeled isoprenoid cytokinins. Phytochemistry. 2018 Jun; 150(?):1-11. doi: 10.1016/j.phytochem.2018.02.015. [PMID: 29524794]
  • Zuzana Gelová, Petra Ten Hoopen, Ondrej Novák, Václav Motyka, Markéta Pernisová, Siarhei Dabravolski, Vojtech Didi, Isolde Tillack, Jana Okleštková, Miroslav Strnad, Bettina Hause, Danka Haruštiaková, Udo Conrad, Lubomír Janda, Jan Hejátko. Antibody-mediated modulation of cytokinins in tobacco: organ-specific changes in cytokinin homeostasis. Journal of experimental botany. 2018 01; 69(3):441-454. doi: 10.1093/jxb/erx426. [PMID: 29294075]
  • Li Zhang, Xu-Hui Li, Zhen Gao, Si Shen, Xiao-Gui Liang, Xue Zhao, Shan Lin, Shun-Li Zhou. Regulation of maize kernel weight and carbohydrate metabolism by abscisic acid applied at the early and middle post-pollination stages in vitro. Journal of plant physiology. 2017 Sep; 216(?):1-10. doi: 10.1016/j.jplph.2017.05.005. [PMID: 28544894]
  • Asami Osugi, Mikiko Kojima, Yumiko Takebayashi, Nanae Ueda, Takatoshi Kiba, Hitoshi Sakakibara. Systemic transport of trans-zeatin and its precursor have differing roles in Arabidopsis shoots. Nature plants. 2017 Jul; 3(?):17112. doi: 10.1038/nplants.2017.112. [PMID: 28737742]
  • Miao Li, Yonghao Qi, Jing Wei, Lulu Lu, Xuan Zhao, Lijun Zhou. N6-Isopentenyladenosine promoted HeLa cell apoptosis through inhibitions of AKT and transforming growth factor β-activated kinase 1 activation. Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine. 2017 Mar; 39(3):1010428317695966. doi: 10.1177/1010428317695966. [PMID: 28345459]
  • Elena Ciaglia, Mario Abate, Chiara Laezza, Simona Pisanti, Mario Vitale, Vincenzo Seneca, Giovanni Torelli, Silvia Franceschelli, Giuseppe Catapano, Patrizia Gazzerro, Maurizio Bifulco. Antiglioma effects of N6-isopentenyladenosine, an endogenous isoprenoid end product, through the downregulation of epidermal growth factor receptor. International journal of cancer. 2017 02; 140(4):959-972. doi: 10.1002/ijc.30505. [PMID: 27813087]
  • Eloy Navarro-León, Alfonso Albacete, Alejandro de la Torre-González, Juan M Ruiz, Begoña Blasco. Phytohormone profile in Lactuca sativa and Brassica oleracea plants grown under Zn deficiency. Phytochemistry. 2016 Oct; 130(?):85-9. doi: 10.1016/j.phytochem.2016.08.003. [PMID: 27543253]
  • Ping Liu, Sai Fan, Guohua Wu, Rong Zhao, Wei Liu, Xudong Zhao. [Determination of 6 kinds of plant growth regulator in bean sprout by ultra high performance liquid chromatography-tandem mass spectrometry]. Wei sheng yan jiu = Journal of hygiene research. 2016 May; 45(3):483-9. doi: . [PMID: 27459816]
  • Imrul Mosaddek Ahmed, Umme Aktari Nadira, Fangbin Cao, Xiaoyan He, Guoping Zhang, Feibo Wu. Physiological and molecular analysis on root growth associated with the tolerance to aluminum and drought individual and combined in Tibetan wild and cultivated barley. Planta. 2016 Apr; 243(4):973-85. doi: 10.1007/s00425-015-2442-x. [PMID: 26748913]
  • Xiangqiang Kong, Zhen Luo, Hezhong Dong, A Egrinya Eneji, Weijiang Li. H2O2 and ABA signaling are responsible for the increased Na+ efflux and water uptake in Gossypium hirsutum L. roots in the non-saline side under non-uniform root zone salinity. Journal of experimental botany. 2016 Apr; 67(8):2247-61. doi: 10.1093/jxb/erw026. [PMID: 26862153]
  • Andrea Ertani, Diego Pizzeghello, Ornella Francioso, Anna Tinti, Serenella Nardi. Biological Activity of Vegetal Extracts Containing Phenols on Plant Metabolism. Molecules (Basel, Switzerland). 2016 Feb; 21(2):. doi: 10.3390/molecules21020205. [PMID: 26867189]
  • Dongqing Yang, Yong Li, Yuhua Shi, Zhengyong Cui, Yongli Luo, Mengjing Zheng, Jin Chen, Yanxia Li, Yanping Yin, Zhenlin Wang. Exogenous Cytokinins Increase Grain Yield of Winter Wheat Cultivars by Improving Stay-Green Characteristics under Heat Stress. PloS one. 2016; 11(5):e0155437. doi: 10.1371/journal.pone.0155437. [PMID: 27203573]
  • Zi-chang Zhang, Yong-feng Li, Xia Yang, Tao Gu, Gui Li. [Effects of different barnyardgrass species on grain yield of rice and their physiological characteristics under alternate wetting and drying irrigation]. Ying yong sheng tai xue bao = The journal of applied ecology. 2015 Nov; 26(11):3389-97. doi: . [PMID: 26915195]
  • Fengxia Wang, Yan-Ge Xu, Shuai Wang, Weiwei Shi, Ranran Liu, Gu Feng, Jie Song. Salinity affects production and salt tolerance of dimorphic seeds of Suaeda salsa. Plant physiology and biochemistry : PPB. 2015 Oct; 95(?):41-8. doi: 10.1016/j.plaphy.2015.07.005. [PMID: 26184090]
  • Venkatesan Radhika, Nanae Ueda, Yuuri Tsuboi, Mikiko Kojima, Jun Kikuchi, Takuji Kudo, Hitoshi Sakakibara. Methylated Cytokinins from the Phytopathogen Rhodococcus fascians Mimic Plant Hormone Activity. Plant physiology. 2015 Oct; 169(2):1118-26. doi: 10.1104/pp.15.00787. [PMID: 26251309]
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  • Christine Böttcher, Crista A Burbidge, Paul K Boss, Christopher Davies. Changes in transcription of cytokinin metabolism and signalling genes in grape (Vitis vinifera L.) berries are associated with the ripening-related increase in isopentenyladenine. BMC plant biology. 2015 Sep; 15(?):223. doi: 10.1186/s12870-015-0611-5. [PMID: 26377914]
  • Janine Hinsch, Josef Vrabka, Birgitt Oeser, Ondřej Novák, Petr Galuszka, Paul Tudzynski. De novo biosynthesis of cytokinins in the biotrophic fungus Claviceps purpurea. Environmental microbiology. 2015 Aug; 17(8):2935-51. doi: 10.1111/1462-2920.12838. [PMID: 25753486]
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  • Ren-hua Huang, Hi-ling Yang, Wei Huang, Yun-mei Lu, Ke Chen. [Effects of Funneliformis mosseae on endogenous hormones and photosynthesis of Sorghum haipense under Cs stress]. Ying yong sheng tai xue bao = The journal of applied ecology. 2015 Jul; 26(7):2146-50. doi: ". [PMID: 26710644]
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