Nicotianamine (BioDeep_00000003340)

 

Secondary id: BioDeep_00000897494, BioDeep_00001892276

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(S,S,S)-nicotianamine

化学式: C12H21N3O6 (303.143)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(otcml) 15.91%

分子结构信息

SMILES: C1CN(C1C(=O)O)CCC(C(=O)O)NCCC(C(=O)O)N
InChI: InChI=1S/C12H21N3O6/c13-7(10(16)17)1-4-14-8(11(18)19)2-5-15-6-3-9(15)12(20)21/h7-9,14H,1-6,13H2,(H,16,17)(H,18,19)(H,20,21)/t7-,8-,9-/m0/s1

描述信息

The (S,S,S)-stereoisomer of nicotianamine.
IPB_RECORD: 2921; CONFIDENCE confident structure

同义名列表

3 个代谢物同义名

(S,S,S)-nicotianamine; Nicotianamine; Nicotianamine



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(0)

BioCyc(0)

PlantCyc(0)

代谢反应

261 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(261)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

68 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
Cytoplasm 8 AHCY, MTAP, MTR, SLC11A2, SLC40A1, TCF3, TOM1, ZIC1
Golgi apparatus, trans-Golgi network membrane 1 SLC11A2
Peripheral membrane protein 1 TOM1
Endosome membrane 3 SLC11A1, SLC11A2, TOM1
Endoplasmic reticulum membrane 2 HSP90B1, PSEN2
Nucleus 7 AHCY, HSP90B1, MTAP, SLC11A2, SMARCAD1, TCF3, ZIC1
cytosol 8 AHCY, HSP90B1, MAT1A, MTAP, MTR, SLC40A1, TCF3, TOM1
trans-Golgi network 1 SLC11A2
centrosome 1 PSEN2
nucleoplasm 6 ATP2B1, MTAP, SLC40A1, SMARCAD1, TCF3, ZIC1
RNA polymerase II transcription regulator complex 1 TCF3
Cell membrane 5 ATP2B1, SLC11A2, SLC36A1, SLC40A1, SLC6A2
Early endosome membrane 2 SLC11A2, TOM1
Multi-pass membrane protein 7 ATP2B1, PSEN2, SLC11A1, SLC11A2, SLC36A1, SLC40A1, SLC6A2
Golgi apparatus membrane 1 PSEN2
Synapse 1 ATP2B1
cell surface 2 SLC11A2, SLC6A2
gamma-secretase complex 1 PSEN2
glutamatergic synapse 1 ATP2B1
Golgi apparatus 2 PSEN2, SLC11A2
Golgi membrane 1 PSEN2
lysosomal membrane 3 SLC11A1, SLC11A2, SLC36A1
presynaptic membrane 3 ATP2B1, PSEN2, SLC6A2
smooth endoplasmic reticulum 1 HSP90B1
synaptic vesicle 2 PSEN2, SLC40A1
Lysosome 2 SLC11A1, SLC11A2
endosome 1 TOM1
plasma membrane 10 ATP2B1, GPRIN2, PSEN2, REN, SLC11A1, SLC11A2, SLC36A1, SLC40A1, SLC6A2, TOM1
synaptic vesicle membrane 2 ATP2B1, SLC6A2
Membrane 9 ATP2B1, HSP90B1, PSEN2, REN, SLC11A2, SLC36A1, SLC40A1, SLC6A2, TOM1
apical plasma membrane 2 SLC11A2, SLC36A1
axon 1 SLC6A2
basolateral plasma membrane 2 ATP2B1, SLC40A1
extracellular exosome 6 AHCY, ATP2B1, CPVL, HSP90B1, MTAP, TOM1
Lysosome membrane 3 SLC11A1, SLC11A2, SLC36A1
endoplasmic reticulum 4 AHCY, HSP90B1, PSEN2, SLC36A1
extracellular space 1 REN
perinuclear region of cytoplasm 2 HSP90B1, SLC11A2
mitochondrion 1 SLC11A2
protein-containing complex 3 HSP90B1, PSEN2, TCF3
intracellular membrane-bounded organelle 1 ATP2B1
Secreted 1 REN
extracellular region 3 HSP90B1, MLN, REN
Mitochondrion outer membrane 1 SLC11A2
Single-pass membrane protein 1 MLN
mitochondrial outer membrane 1 SLC11A2
basal part of cell 1 SLC11A2
neuronal cell body membrane 1 SLC6A2
transcription regulator complex 1 TCF3
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Extracellular vesicle 1 SLC11A2
cytoplasmic vesicle 1 SLC11A2
midbody 1 HSP90B1
Early endosome 3 PSEN2, SLC11A2, TOM1
apical part of cell 2 REN, SLC11A2
recycling endosome 1 SLC11A2
Apical cell membrane 2 SLC11A2, SLC36A1
heterochromatin 1 SMARCAD1
focal adhesion 1 HSP90B1
collagen-containing extracellular matrix 1 HSP90B1
lateral plasma membrane 2 ATP2B1, SLC40A1
nuclear inner membrane 1 PSEN2
Late endosome 2 SLC11A1, SLC11A2
chromatin 1 TCF3
Late endosome membrane 2 SLC11A1, SLC11A2
cell projection 1 ATP2B1
phagocytic vesicle membrane 1 SLC11A1
brush border membrane 1 SLC11A2
nuclear replication fork 1 SMARCAD1
Basolateral cell membrane 2 ATP2B1, SLC40A1
site of double-strand break 1 SMARCAD1
Recycling endosome membrane 1 SLC11A2
Endomembrane system 1 PSEN2
specific granule membrane 1 TOM1
tertiary granule membrane 1 SLC11A1
Melanosome 2 AHCY, HSP90B1
euchromatin 1 TCF3
Presynaptic cell membrane 1 ATP2B1
sperm plasma membrane 1 HSP90B1
endoplasmic reticulum lumen 1 HSP90B1
kinetochore 1 PSEN2
azurophil granule membrane 1 TOM1
beta-catenin-TCF complex 1 TCF3
Sarcoplasmic reticulum membrane 1 MLN
immunological synapse 1 ATP2B1
Sarcoplasmic reticulum lumen 1 HSP90B1
Vacuole 1 SLC11A2
ficolin-1-rich granule membrane 1 SLC11A1
[Isoform 3]: Cell membrane 1 SLC11A2
endocytic vesicle lumen 1 HSP90B1
Extracellular vesicle membrane 1 SLC11A2
vacuolar membrane 1 SLC36A1
endoplasmic reticulum chaperone complex 1 HSP90B1
photoreceptor ribbon synapse 1 ATP2B1
methionine adenosyltransferase complex 1 MAT1A
[Isoform 1]: Early endosome membrane 1 SLC11A2
[Isoform 2]: Late endosome membrane 1 SLC11A2
paraferritin complex 1 SLC11A2


文献列表

  • Xi Wu, Yafeng Jia, Qian Ma, Tingting Wang, Jiena Xu, Hongli Chen, Mingxia Wang, Hui Song, Shuqing Cao. The transcription factor bZIP44 cooperates with MYB10 and MYB72 to regulate the response of Arabidopsis thaliana to iron deficiency stress. The New phytologist. 2024 Jun; 242(6):2586-2603. doi: 10.1111/nph.19706. [PMID: 38523234]
  • Ilya V Seregin, Anna D Kozhevnikova. Nicotianamine: A Key Player in Metal Homeostasis and Hyperaccumulation in Plants. International journal of molecular sciences. 2023 Jun; 24(13):. doi: 10.3390/ijms241310822. [PMID: 37446000]
  • Hiroyuki Seebach, Gabriel Radow, Michael Brunek, Frank Schulz, Markus Piotrowski, Ute Krämer. Arabidopsis Nicotianamine Synthases (NAS) comprise a common core-NAS domain fused to a variable auto-inhibitory C-terminus. The Journal of biological chemistry. 2023 Apr; ?(?):104732. doi: 10.1016/j.jbc.2023.104732. [PMID: 37086785]
  • Wentao Sun, Xiaojin J Zhou, Chen Chen, Xin Zhang, Xiaolong Tian, Ke Xiao, Chenxu Liu, Rumei Chen, Shaojiang Chen. Maize Interveinal Chlorosis 1 links the Yang Cycle and Fe homeostasis through Nicotianamine biosynthesis. Plant physiology. 2022 03; 188(4):2131-2145. doi: 10.1093/plphys/kiac009. [PMID: 35099564]
  • Jesse T Beasley, Julien P Bonneau, Laura T Moreno-Moyano, Damien L Callahan, Kate S Howell, Elad Tako, Julian Taylor, Raymond P Glahn, Rudi Appels, Alexander A T Johnson. Multi-year field evaluation of nicotianamine biofortified bread wheat. The Plant journal : for cell and molecular biology. 2022 03; 109(5):1168-1182. doi: 10.1111/tpj.15623. [PMID: 34902177]
  • S Gopika, Cyril Augustine. Theoretical studies on the coordination chemistry of phytosiderophores with special reference to Fe-nicotianamine complexes in graminaceous plants. Journal of molecular modeling. 2022 Feb; 28(3):71. doi: 10.1007/s00894-022-05065-3. [PMID: 35226207]
  • Xin Zhang, Ke Xiao, Suzhen Li, Jie Li, Jiaxing Huang, Rumei Chen, Sen Pang, Xiaojin Zhou. Genome-wide analysis of the NAAT, DMAS, TOM, and ENA gene families in maize suggests their roles in mediating iron homeostasis. BMC plant biology. 2022 Jan; 22(1):37. doi: 10.1186/s12870-021-03422-7. [PMID: 35039017]
  • Ghaya Alchoubassi, Katarzyna Kińska, Katarzyna Bierla, Ryszard Lobinski, Joanna Szpunar. Speciation of essential nutrient trace elements in coconut water. Food chemistry. 2021 Mar; 339(?):127680. doi: 10.1016/j.foodchem.2020.127680. [PMID: 32860999]
  • Yoshiko Murata, Masami Yoshida, Naho Sakamoto, Shiho Morimoto, Takehiro Watanabe, Kosuke Namba. Iron uptake mediated by the plant-derived chelator nicotianamine in the small intestine. The Journal of biological chemistry. 2021 Jan; 296(?):100195. doi: 10.1074/jbc.ra120.015861. [PMID: 33334885]
  • James F Collins. Iron chelates hitch a ride on PAT1. The Journal of biological chemistry. 2021 Jan; 296(?):100418. doi: 10.1016/j.jbc.2021.100418. [PMID: 33837730]
  • Clémentine Laffont, Pascal Arnoux. The ancient roots of nicotianamine: diversity, role, regulation and evolution of nicotianamine-like metallophores. Metallomics : integrated biometal science. 2020 10; 12(10):1480-1493. doi: 10.1039/d0mt00150c. [PMID: 33084706]
  • Yuta Kawakami, Navreet K Bhullar. Potential Implications of Interactions between Fe and S on Cereal Fe Biofortification. International journal of molecular sciences. 2020 Apr; 21(8):. doi: 10.3390/ijms21082827. [PMID: 32325653]
  • Huimin Zhang, Yang Li, Mengna Pu, Peng Xu, Gang Liang, Diqiu Yu. Oryza sativa POSITIVE REGULATOR OF IRON DEFICIENCY RESPONSE 2 (OsPRI2) and OsPRI3 are involved in the maintenance of Fe homeostasis. Plant, cell & environment. 2020 01; 43(1):261-274. doi: 10.1111/pce.13655. [PMID: 31674679]
  • Ruohan Xie, Jianqi Zhao, Lingli Lu, Jun Ge, Patrick H Brown, Shuai Wei, Runze Wang, Yabei Qiao, Samuel M Webb, Shengke Tian. Efficient phloem remobilization of Zn protects apple trees during the early stages of Zn deficiency. Plant, cell & environment. 2019 12; 42(12):3167-3181. doi: 10.1111/pce.13621. [PMID: 31325325]
  • Houqing Zeng, Xin Zhang, Ming Ding, Xiajun Zhang, Yiyong Zhu. Transcriptome profiles of soybean leaves and roots in response to zinc deficiency. Physiologia plantarum. 2019 Nov; 167(3):330-351. doi: 10.1111/ppl.12894. [PMID: 30536844]
  • Raviraj Banakar, Ana Alvarez Fernandez, Changfu Zhu, Javier Abadia, Teresa Capell, Paul Christou. The ratio of phytosiderophores nicotianamine to deoxymugenic acid controls metal homeostasis in rice. Planta. 2019 Oct; 250(4):1339-1354. doi: 10.1007/s00425-019-03230-2. [PMID: 31278466]
  • Shaopei Gao, Yunhua Xiao, Fan Xu, Xiaokai Gao, Shouyun Cao, Fengxia Zhang, Guodong Wang, Dale Sanders, Chengcai Chu. Cytokinin-dependent regulatory module underlies the maintenance of zinc nutrition in rice. The New phytologist. 2019 10; 224(1):202-215. doi: 10.1111/nph.15962. [PMID: 31131881]
  • Jesse T Beasley, Julien P Bonneau, Jose T Sánchez-Palacios, Laura T Moreno-Moyano, Damien L Callahan, Elad Tako, Raymond P Glahn, Enzo Lombi, Alexander A T Johnson. Metabolic engineering of bread wheat improves grain iron concentration and bioavailability. Plant biotechnology journal. 2019 08; 17(8):1514-1526. doi: 10.1111/pbi.13074. [PMID: 30623558]
  • Jesse T Beasley, Jonathan J Hart, Elad Tako, Raymond P Glahn, Alexander A T Johnson. Investigation of Nicotianamine and 2' Deoxymugineic Acid as Enhancers of Iron Bioavailability in Caco-2 Cells. Nutrients. 2019 Jun; 11(7):. doi: 10.3390/nu11071502. [PMID: 31262064]
  • Shimpei Uraguchi, Michael Weber, Stephan Clemens. Elevated root nicotianamine concentrations are critical for Zn hyperaccumulation across diverse edaphic environments. Plant, cell & environment. 2019 06; 42(6):2003-2014. doi: 10.1111/pce.13541. [PMID: 30809818]
  • Xinxin Zhang, Di Zhang, Wei Sun, Tianzuo Wang. The Adaptive Mechanism of Plants to Iron Deficiency via Iron Uptake, Transport, and Homeostasis. International journal of molecular sciences. 2019 May; 20(10):. doi: 10.3390/ijms20102424. [PMID: 31100819]
  • Brigitta Müller, Krisztina Kovács, Hong-Diep Pham, Yusuf Kavak, Jiři Pechoušek, Libor Machala, Radek Zbořil, Kálmán Szenthe, Javier Abadía, Ferenc Fodor, Zoltán Klencsár, Ádám Solti. Chloroplasts preferentially take up ferric-citrate over iron-nicotianamine complexes in Brassica napus. Planta. 2019 Mar; 249(3):751-763. doi: 10.1007/s00425-018-3037-0. [PMID: 30382344]
  • Alessio Aprile, Erika Sabella, Marzia Vergine, Alessandra Genga, Maria Siciliano, Eliana Nutricati, Patrizia Rampino, Mariarosaria De Pascali, Andrea Luvisi, Antonio Miceli, Carmine Negro, Luigi De Bellis. Activation of a gene network in durum wheat roots exposed to cadmium. BMC plant biology. 2018 Oct; 18(1):238. doi: 10.1186/s12870-018-1473-4. [PMID: 30326849]
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  • Rakesh K Kumar, Heng-Hsuan Chu, Celina Abundis, Kenneth Vasques, David Chan Rodriguez, Ju-Chen Chia, Rong Huang, Olena K Vatamaniuk, Elsbeth L Walker. Iron-Nicotianamine Transporters Are Required for Proper Long Distance Iron Signaling. Plant physiology. 2017 Nov; 175(3):1254-1268. doi: 10.1104/pp.17.00821. [PMID: 28894019]
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  • Dong-Keun Lee, Pil Joong Chung, Jin Seo Jeong, Geupil Jang, Seung Woon Bang, Harin Jung, Youn Shic Kim, Sun-Hwa Ha, Yang Do Choi, Ju-Kon Kim. The rice OsNAC6 transcription factor orchestrates multiple molecular mechanisms involving root structural adaptions and nicotianamine biosynthesis for drought tolerance. Plant biotechnology journal. 2017 Jun; 15(6):754-764. doi: 10.1111/pbi.12673. [PMID: 27892643]
  • Chandan Kumar Gupta, Bhupinder Singh. Uninhibited biosynthesis and release of phytosiderophores in the presence of heavy metal (HM) favors HM remediation. Environmental science and pollution research international. 2017 Apr; 24(10):9407-9416. doi: 10.1007/s11356-017-8636-y. [PMID: 28233213]
  • Weilin Zhang, Chengqi Yan, Mei Li, Ling Yang, Bojun Ma, Hongyu Meng, Li Xie, Jianping Chen. Transcriptome Analysis Reveals the Response of Iron Homeostasis to Early Feeding by Small Brown Planthopper in Rice. Journal of agricultural and food chemistry. 2017 Feb; 65(6):1093-1101. doi: 10.1021/acs.jafc.6b04674. [PMID: 28112511]
  • Jelena Pavlovic, Jelena Samardzic, Ljiljana Kostic, Kristian H Laursen, Maja Natic, Gordana Timotijevic, Jan K Schjoerring, Miroslav Nikolic. Silicon enhances leaf remobilization of iron in cucumber under limited iron conditions. Annals of botany. 2016 08; 118(2):271-80. doi: 10.1093/aob/mcw105. [PMID: 27371693]
  • Ghassan Ghssein, Catherine Brutesco, Laurent Ouerdane, Clémentine Fojcik, Amélie Izaute, Shuanglong Wang, Christine Hajjar, Ryszard Lobinski, David Lemaire, Pierre Richaud, Romé Voulhoux, Akbar Espaillat, Felipe Cava, David Pignol, Elise Borezée-Durant, Pascal Arnoux. Biosynthesis of a broad-spectrum nicotianamine-like metallophore in Staphylococcus aureus. Science (New York, N.Y.). 2016 May; 352(6289):1105-9. doi: 10.1126/science.aaf1018. [PMID: 27230378]
  • Tomoko Ariga, Yuki Imura, Michio Suzuki, Etsuro Yoshimura. Determination of ferric iron chelators by high-performance liquid chromatography using luminol chemiluminescence detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Mar; 1014(?):75-82. doi: 10.1016/j.jchromb.2016.01.048. [PMID: 26874881]
  • Tadakatsu Yoneyama, Satoru Ishikawa, Shu Fujimaki. Route and Regulation of Zinc, Cadmium, and Iron Transport in Rice Plants (Oryza sativa L.) during Vegetative Growth and Grain Filling: Metal Transporters, Metal Speciation, Grain Cd Reduction and Zn and Fe Biofortification. International journal of molecular sciences. 2015 Aug; 16(8):19111-29. doi: 10.3390/ijms160819111. [PMID: 26287170]
  • Kenji Hazama, Shinji Nagata, Tamaki Fujimori, Shuichi Yanagisawa, Tadakatsu Yoneyama. Concentrations of metals and potential metal-binding compounds and speciation of Cd, Zn and Cu in phloem and xylem saps from castor bean plants (Ricinus communis) treated with four levels of cadmium. Physiologia plantarum. 2015 Jun; 154(2):243-55. doi: 10.1111/ppl.12309. [PMID: 25403762]
  • Ryo Nakabayashi, Zhigang Yang, Tomoko Nishizawa, Tetsuya Mori, Kazuki Saito. Top-down Targeted Metabolomics Reveals a Sulfur-Containing Metabolite with Inhibitory Activity against Angiotensin-Converting Enzyme in Asparagus officinalis. Journal of natural products. 2015 May; 78(5):1179-83. doi: 10.1021/acs.jnatprod.5b00092. [PMID: 25922884]
  • Jean-Yves Cornu, Ulrich Deinlein, Stephan Höreth, Manuel Braun, Holger Schmidt, Michael Weber, Daniel P Persson, Søren Husted, Jan K Schjoerring, Stephan Clemens. Contrasting effects of nicotianamine synthase knockdown on zinc and nickel tolerance and accumulation in the zinc/cadmium hyperaccumulator Arabidopsis halleri. The New phytologist. 2015 Apr; 206(2):738-50. doi: 10.1111/nph.13237. [PMID: 25545296]
  • Saori Takahashi, Taku Yoshiya, Kumiko Yoshizawa-Kumagaye, Toshihiro Sugiyama. Nicotianamine is a novel angiotensin-converting enzyme 2 inhibitor in soybean. Biomedical research (Tokyo, Japan). 2015; 36(3):219-24. doi: 10.2220/biomedres.36.219. [PMID: 26106051]
  • Munkhtsetseg Tsednee, Shun-Chung Yang, Der-Chuen Lee, Kuo-Chen Yeh. Root-secreted nicotianamine from Arabidopsis halleri facilitates zinc hypertolerance by regulating zinc bioavailability. Plant physiology. 2014 Oct; 166(2):839-52. doi: 10.1104/pp.114.241224. [PMID: 25118254]
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  • Emmanuel Koen, Angélique Besson-Bard, Céline Duc, Jérémy Astier, Antoine Gravot, Pierre Richaud, Olivier Lamotte, Jossia Boucherez, Frédéric Gaymard, David Wendehenne. Arabidopsis thaliana nicotianamine synthase 4 is required for proper response to iron deficiency and to cadmium exposure. Plant science : an international journal of experimental plant biology. 2013 Aug; 209(?):1-11. doi: 10.1016/j.plantsci.2013.04.006. [PMID: 23759098]
  • Stephan Clemens, Ulrich Deinlein, Hassan Ahmadi, Stephan Höreth, Shimpei Uraguchi. Nicotianamine is a major player in plant Zn homeostasis. Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine. 2013 Aug; 26(4):623-32. doi: 10.1007/s10534-013-9643-1. [PMID: 23775667]
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  • Hitomi Yamaguchi, Riichiro Uchida. Determination of nicotianamine in soy sauce and other plant-based foods by LC-MS/MS. Journal of agricultural and food chemistry. 2012 Oct; 60(40):10000-6. doi: 10.1021/jf3035868. [PMID: 23025624]
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  • Luqing Zheng, Naoki Yamaji, Kengo Yokosho, Jian Feng Ma. YSL16 is a phloem-localized transporter of the copper-nicotianamine complex that is responsible for copper distribution in rice. The Plant cell. 2012 Sep; 24(9):3767-82. doi: 10.1105/tpc.112.103820. [PMID: 23012434]
  • Rongli Shi, Günther Weber, Jessica Köster, Mohammad Reza-Hajirezaei, Chunqin Zou, Fusuo Zhang, Nicolaus von Wirén. Senescence-induced iron mobilization in source leaves of barley (Hordeum vulgare) plants. The New phytologist. 2012 Jul; 195(2):372-383. doi: 10.1111/j.1469-8137.2012.04165.x. [PMID: 22591276]
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