Canavanine (BioDeep_00000001363)

 

Secondary id: BioDeep_00001867933

natural product human metabolite


代谢物信息卡片


(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoic acid

化学式: C5H12N4O3 (176.0909362)
中文名称: L-刀豆氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 1.88%

分子结构信息

SMILES: C(CON=C(N)N)C(C(=O)O)N
InChI: InChI=1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)

描述信息

L-Canavanine, a non-protein amino acid of certain leguminous plants, is related structurally to the protein amino acid, L-arginine. Canavanine is accumulated primarily in the seeds where it serves both as a defensive compound against herbivores and a vital source of nitrogen for the growing embryo. Organisms that consume it can mistakenly incorporate it into their own proteins, in the place of arginine thereby producing structurally aberrant proteins that may not function properly or not at all. Some specialized herbivores tolerate L-canavanine either because they metabolize it efficiently or avoid its incorporation into their own nascent proteins.
Stored in large quantities in the seeds of leguminous plants in three subfamilies. Isol. originally from Jackbean (Canavalia ensiformis)
KEIO_ID C094

同义名列表

12 个代谢物同义名

(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoic acid; (2S)-2-amino-4-(carbamimidamidooxy)butanoic acid; (2S)-2-Ammonio-4-(carbamimidamidooxy)butanoate; O-((Aminoiminomethyl)amino)homoserine; 2-Amino-4-(guanidinooxy)butyric acid; L-2-Amino-4-(guanidinooxy)butyrate; 2-Amino-4-(guanidinooxy)butyrate; (L)-Canavanine; DL-Canavanine; L-Canavanine; Canavanine; Canavanin



数据库引用编号

37 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

116 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(116)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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

  • Sara Abouzeid, Ulrike Beutling, Engy Elekhnawy, Dirk Selmar. Antibacterial and Antibiofilm Effects of Allelopathic Compounds Identified in Medicago sativa L. Seedling Exudate against Escherichia coli. Molecules (Basel, Switzerland). 2023 Mar; 28(6):. doi: 10.3390/molecules28062645. [PMID: 36985619]
  • Einar Artiles-Ortega, Pedro Yoelvys de la Fé-Rodríguez, Beydis Reguera-Barreto, Raciel Lima-Orozco, Veerle Fievez. In vitro rumen degradability of tropical legumes and their secondary metabolites depends on inoculum source. Tropical animal health and production. 2022 Sep; 54(5):330. doi: 10.1007/s11250-022-03327-z. [PMID: 36173493]
  • Alena Aliashkevich, Matthew Howell, Pamela J B Brown, Felipe Cava. d-canavanine affects peptidoglycan structure, morphogenesis and fitness in Rhizobiales. Environmental microbiology. 2021 10; 23(10):5823-5836. doi: 10.1111/1462-2920.15513. [PMID: 33830599]
  • 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]
  • Olena Karatsai, Pavel Shliaha, Ole N Jensen, Oleh Stasyk, Maria Jolanta Rędowicz. Combinatory Treatment of Canavanine and Arginine Deprivation Efficiently Targets Human Glioblastoma Cells via Pleiotropic Mechanisms. Cells. 2020 09; 9(10):. doi: 10.3390/cells9102217. [PMID: 33008000]
  • Pawel Staszek, Agnieszka Gniazdowska. Peroxynitrite induced signaling pathways in plant response to non-proteinogenic amino acids. Planta. 2020 Jun; 252(1):5. doi: 10.1007/s00425-020-03411-4. [PMID: 32535658]
  • Marina Druseikis, Julius Ben-Ari, Shay Covo. The Goldilocks effect of respiration on canavanine tolerance in Saccharomyces cerevisiae. Current genetics. 2019 Oct; 65(5):1199-1215. doi: 10.1007/s00294-019-00974-y. [PMID: 31011791]
  • Dan-Qian Chen, Gang Cao, Hua Chen, Christos P Argyopoulos, Hui Yu, Wei Su, Lin Chen, David C Samuels, Shougang Zhuang, George P Bayliss, Shilin Zhao, Xiao-Yong Yu, Nosratola D Vaziri, Ming Wang, Dan Liu, Jia-Rong Mao, Shi-Xing Ma, Jin Zhao, Yuan Zhang, You-Quan Shang, Huining Kang, Fei Ye, Xiao-Hong Cheng, Xiang-Ri Li, Li Zhang, Mei-Xia Meng, Yan Guo, Ying-Yong Zhao. Identification of serum metabolites associating with chronic kidney disease progression and anti-fibrotic effect of 5-methoxytryptophan. Nature communications. 2019 04; 10(1):1476. doi: 10.1038/s41467-019-09329-0. [PMID: 30931940]
  • Piotr Soczewka, Damian Kolakowski, Iwona Smaczynska-de Rooij, Weronika Rzepnikowska, Kathryn R Ayscough, Joanna Kaminska, Teresa Zoladek. Yeast-model-based study identified myosin- and calcium-dependent calmodulin signalling as a potential target for drug intervention in chorea-acanthocytosis. Disease models & mechanisms. 2019 01; 12(1):. doi: 10.1242/dmm.036830. [PMID: 30635263]
  • Christoph Mathieu, Juan P Macêdo, Daniel Hürlimann, Corina Wirdnam, Alexander C Haindrich, Marianne Suter Grotemeyer, Amaia González-Salgado, Remo S Schmidt, Ehud Inbar, Pascal Mäser, Peter Bütikofer, Dan Zilberstein, Doris Rentsch. Arginine and Lysine Transporters Are Essential for Trypanosoma brucei. PloS one. 2017; 12(1):e0168775. doi: 10.1371/journal.pone.0168775. [PMID: 28045943]
  • Urszula Krasuska, Olga Andrzejczak, Paweł Staszek, Wojciech Borucki, Agnieszka Gniazdowska. Toxicity of canavanine in tomato (Solanum lycopersicum L.) roots is due to alterations in RNS, ROS and auxin levels. Plant physiology and biochemistry : PPB. 2016 Jun; 103(?):84-95. doi: 10.1016/j.plaphy.2016.03.005. [PMID: 26986929]
  • O I Vovk, O I Chen, N I Igumentseva, O Yu Senchuk, M L Barska, N O Sybirna, O V Stasyk. Effects of the combined arginase and canavanine treatment on leukemic cells in vitro and in vivo. Ukrainian biochemical journal. 2016 Mar; 88(2):45-55. doi: 10.15407/ubj88.02.045. [PMID: 29227602]
  • Yaroslav Bobak, Yuliya Kurlishchuk, Bozhena Vynnytska-Myronovska, Olesia Grydzuk, Galyna Shuvayeva, Maria J Redowicz, Leoni A Kunz-Schughart, Oleh Stasyk. Arginine deprivation induces endoplasmic reticulum stress in human solid cancer cells. The international journal of biochemistry & cell biology. 2016 Jan; 70(?):29-38. doi: 10.1016/j.biocel.2015.10.027. [PMID: 26546743]
  • Jaewon Shim, Youngseok Lee, Yong Taek Jeong, Yonjung Kim, Min Goo Lee, Craig Montell, Seok Jun Moon. The full repertoire of Drosophila gustatory receptors for detecting an aversive compound. Nature communications. 2015 Nov; 6(?):8867. doi: 10.1038/ncomms9867. [PMID: 26568264]
  • Chin-Hong Chang, Pin-Chun Chao, Ho-Shan Niu, Gin-Chi Huang, Li-Jen Chen, Juei-Tang Cheng. Canavanine activates imidazoline I-2 receptors to reduce hyperglycemia in type 1-like diabetic rats. Chemico-biological interactions. 2015 Oct; 240(?):304-9. doi: 10.1016/j.cbi.2015.08.019. [PMID: 26362499]
  • Tsunashi Kamo, Sakae Sakurai, Tatsuya Yamanashi, Yasushi Todoroki. Cyanamide is biosynthesized from L-canavanine in plants. Scientific reports. 2015 May; 5(?):10527. doi: 10.1038/srep10527. [PMID: 26013398]
  • Ting-Ting Yang, Ho-Shan Niu, Li-Jen Chen, Po-Ming Ku, Kao-Chang Lin, Juei-Tang Cheng. Canavanine induces insulin release via activation of imidazoline I3 receptors. Clinical and experimental pharmacology & physiology. 2015 Mar; 42(3):263-8. doi: 10.1111/1440-1681.12348. [PMID: 25482045]
  • Y Nakatsuka, T Nagasawa, Y Yumoto, F Nakazawa, Y Furuichi. Inhibitory effects of sword bean extract on alveolar bone resorption induced in rats by Porphyromonas gingivalis infection. Journal of periodontal research. 2014 Dec; 49(6):801-9. doi: 10.1111/jre.12166. [PMID: 24494651]
  • Anne-Katrin Leisinger, Daniel H Janzen, Winnie Hallwachs, Gabor L Igloi. Amino acid discrimination by the nuclear encoded mitochondrial arginyl-tRNA synthetase of the larva of a bruchid beetle (Caryedes brasiliensis) from northwestern Costa Rica. Insect biochemistry and molecular biology. 2013 Dec; 43(12):1172-80. doi: 10.1016/j.ibmb.2013.10.004. [PMID: 24446543]
  • Isabelle Devambez, Moutaz Ali Agha, Christian Mitri, Joël Bockaert, Marie-Laure Parmentier, Frédéric Marion-Poll, Yves Grau, Laurent Soustelle. Gαo is required for L-canavanine detection in Drosophila. PloS one. 2013; 8(5):e63484. doi: 10.1371/journal.pone.0063484. [PMID: 23671680]
  • Carolin A Aldinger, Anne-Katrin Leisinger, Gabor L Igloi. The influence of identity elements on the aminoacylation of tRNA(Arg) by plant and Escherichia coli arginyl-tRNA synthetases. The FEBS journal. 2012 Oct; 279(19):3622-3638. doi: 10.1111/j.1742-4658.2012.08722.x. [PMID: 22831759]
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  • Youngseok Lee, Min Jung Kang, Jaewon Shim, Chae Uk Cheong, Seok Jun Moon, Craig Montell. Gustatory receptors required for avoiding the insecticide L-canavanine. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2012 Jan; 32(4):1429-35. doi: 10.1523/jneurosci.4630-11.2012. [PMID: 22279227]
  • Xiaowei Nie, Shasha Song, Lei Zhang, Zhaoping Qiu, Shuai Shi, Yun Liu, Lan Yao, Daling Zhu. 15-Hydroxyeicosatetraenoic acid (15-HETE) protects pulmonary artery smooth muscle cells from apoptosis via inducible nitric oxide synthase (iNOS) pathway. Prostaglandins & other lipid mediators. 2012 Jan; 97(1-2):50-9. doi: 10.1016/j.prostaglandins.2011.11.003. [PMID: 22101001]
  • Yonatan Herzig, Hayley J Sharpe, Yael Elbaz, Sean Munro, Maya Schuldiner. A systematic approach to pair secretory cargo receptors with their cargo suggests a mechanism for cargo selection by Erv14. PLoS biology. 2012; 10(5):e1001329. doi: 10.1371/journal.pbio.1001329. [PMID: 22629230]
  • Adrienne C Müller, Srinivas Patnala, Olena Kis, Reina Bendayan, Isadore Kanfer. Interactions between phytochemical components of Sutherlandia frutescens and the antiretroviral, atazanavir in vitro: implications for absorption and metabolism. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2012; 15(2):221-33. doi: 10.18433/j3ns3x. [PMID: 22579002]
  • Vinoy K Ramachandran, Alison K East, Ramakrishnan Karunakaran, J Allan Downie, Philip S Poole. Adaptation of Rhizobium leguminosarum to pea, alfalfa and sugar beet rhizospheres investigated by comparative transcriptomics. Genome biology. 2011 Oct; 12(10):R106. doi: 10.1186/gb-2011-12-10-r106. [PMID: 22018401]
  • A Aliahmadi, R Roghanian, G Emtiazi, A Ghassempour. A simple method for primary screening of antibacterial peptides in plant seeds. Iranian journal of microbiology. 2011 Jun; 3(2):104-8. doi: ". [PMID: 22347591]
  • Bozhena O Vynnytska, Oksana M Mayevska, Yuliya V Kurlishchuk, Yaroslav P Bobak, Oleh V Stasyk. Canavanine augments proapoptotic effects of arginine deprivation in cultured human cancer cells. Anti-cancer drugs. 2011 Feb; 22(2):148-57. doi: 10.1097/cad.0b013e32833e0334. [PMID: 20717004]
  • Janine Colling, Marietjie A Stander, Nokwanda P Makunga. Nitrogen supply and abiotic stress influence canavanine synthesis and the productivity of in vitro regenerated Sutherlandia frutescens microshoots. Journal of plant physiology. 2010 Nov; 167(17):1521-4. doi: 10.1016/j.jplph.2010.05.018. [PMID: 20674074]
  • Mohamed A Haidara, Mohamed D Morsy, Hesham A Abdel-Razek, Dimitri P Mikhailidis, Esma R Isenovic. Effects of L-canavanine and ozone on vascular reactivity in septicemic rats. Journal of physiology and biochemistry. 2010 Sep; 66(3):255-64. doi: 10.1007/s13105-010-0034-6. [PMID: 20652469]
  • Pengjuan Gong, Junhong Zhang, Hanxia Li, Changxian Yang, Chanjuan Zhang, Xiaohui Zhang, Ziaf Khurram, Yuyang Zhang, Taotao Wang, Zhangjun Fei, Zhibiao Ye. Transcriptional profiles of drought-responsive genes in modulating transcription signal transduction, and biochemical pathways in tomato. Journal of experimental botany. 2010 Aug; 61(13):3563-75. doi: 10.1093/jxb/erq167. [PMID: 20643807]
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