Chrysanthemic acid (BioDeep_00000003870)

 

Secondary id: BioDeep_00000395511, BioDeep_00001868653

natural product PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


Cyclopropanecarboxylicacid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-

化学式: C10H16O2 (168.1150236)
中文名称: 菊甲酸, ( )-反式-菊酸, 菊花酸
谱图信息: 最多检出来源 Viridiplantae(plant) 6.08%

分子结构信息

SMILES: C1([C@H]([C@H]1C(=O)O)C=C(C)C)(C)C
InChI: InChI=1S/C10H16O2/c1-6(2)5-7-8(9(11)12)10(7,3)4/h5,7-8H,1-4H3,(H,11,12)

描述信息

D010575 - Pesticides > D007306 - Insecticides > D011722 - Pyrethrins

同义名列表

6 个代谢物同义名

Chrysanthemic acid; Cyclopropanecarboxylicacid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-; (+)-trans-Chrysanthemic acid; TRANS-(+)-CHRYSANTHEMIC ACID; Chrysanthemic acid; Chrysanthemic acid



数据库引用编号

33 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

11 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

  • Ying Wang, Jing Wen, Lang Liu, Jing Chen, Chu Wang, Zhengguo Li, Guodong Wang, Eran Pichersky, Haiyang Xu. Engineering of tomato type VI glandular trichomes for trans-chrysanthemic acid biosynthesis, the acid moiety of natural pyrethrin insecticides. Metabolic engineering. 2022 07; 72(?):188-199. doi: 10.1016/j.ymben.2022.03.007. [PMID: 35339691]
  • Magdalena Danek, Joanna Plonka, Hanna Barchanska. Metabolic profiles and non-targeted LC-MS/MS approach as a complementary tool to targeted analysis in assessment of plant exposure to pesticides. Food chemistry. 2021 Sep; 356(?):129680. doi: 10.1016/j.foodchem.2021.129680. [PMID: 33819787]
  • Haiyang Xu, Daniel Lybrand, Stefan Bennewitz, Alain Tissier, Robert L Last, Eran Pichersky. Production of trans-chrysanthemic acid, the monoterpene acid moiety of natural pyrethrin insecticides, in tomato fruit. Metabolic engineering. 2018 05; 47(?):271-278. doi: 10.1016/j.ymben.2018.04.004. [PMID: 29649589]
  • Haiyang Xu, Gaurav D Moghe, Krystle Wiegert-Rininger, Anthony L Schilmiller, Cornelius S Barry, Robert L Last, Eran Pichersky. Coexpression Analysis Identifies Two Oxidoreductases Involved in the Biosynthesis of the Monoterpene Acid Moiety of Natural Pyrethrin Insecticides in Tanacetum cinerariifolium. Plant physiology. 2018 01; 176(1):524-537. doi: 10.1104/pp.17.01330. [PMID: 29122986]
  • Jianjia Fan, Shahab Zareyan, Wenchen Zhao, Yoko Shimizu, Tom A Pfeifer, Jun-Hyung Tak, Murray B Isman, Bernard Van den Hoven, Mark E Duggan, Michael W Wood, Cheryl L Wellington, Iva Kulic. Identification of a Chrysanthemic Ester as an Apolipoprotein E Inducer in Astrocytes. PloS one. 2016; 11(9):e0162384. doi: 10.1371/journal.pone.0162384. [PMID: 27598782]
  • Aldana M Ramirez, Geert Stoopen, Tila R Menzel, Rieta Gols, Harro J Bouwmeester, Marcel Dicke, Maarten A Jongsma. Bidirectional secretions from glandular trichomes of pyrethrum enable immunization of seedlings. The Plant cell. 2012 Oct; 24(10):4252-65. doi: 10.1105/tpc.112.105031. [PMID: 23104830]
  • Yukio Kikuta, Hirokazu Ueda, Masafumi Takahashi, Tomonori Mitsumori, Gen Yamada, Koji Sakamori, Kengo Takeda, Shogo Furutani, Koji Nakayama, Yoshio Katsuda, Akikazu Hatanaka, Kazuhiko Matsuda. Identification and characterization of a GDSL lipase-like protein that catalyzes the ester-forming reaction for pyrethrin biosynthesis in Tanacetum cinerariifolium- a new target for plant protection. The Plant journal : for cell and molecular biology. 2012 Jul; 71(2):183-93. doi: 10.1111/j.1365-313x.2012.04980.x. [PMID: 22385412]
  • John E Casida. The greening of pesticide-environment interactions: some personal observations. Environmental health perspectives. 2012 Apr; 120(4):487-93. doi: 10.1289/ehp.1104405. [PMID: 22472325]
  • Peter P Egeghy, Elaine A Cohen Hubal, Nicolle S Tulve, Lisa J Melnyk, Marsha K Morgan, Roy C Fortmann, Linda S Sheldon. Review of pesticide urinary biomarker measurements from selected US EPA children's observational exposure studies. International journal of environmental research and public health. 2011 05; 8(5):1727-54. doi: 10.3390/ijerph8051727. [PMID: 21655147]
  • Dana Boyd Barr, Anders O Olsson, Lee-Yang Wong, Simeon Udunka, Samuel E Baker, Ralph D Whitehead, Melina S Magsumbol, Bryan L Williams, Larry L Needham. Urinary concentrations of metabolites of pyrethroid insecticides in the general U.S. population: National Health and Nutrition Examination Survey 1999-2002. Environmental health perspectives. 2010 Jun; 118(6):742-8. doi: 10.1289/ehp.0901275. [PMID: 20129874]
  • Takuo Fujisawa, Yoshihide Matoba, Toshiyuki Katagi. Application of separated leaf cell suspension to xenobiotic metabolism in plant. Journal of agricultural and food chemistry. 2009 Aug; 57(15):6982-9. doi: 10.1021/jf901245t. [PMID: 19722580]
  • Gabriele Leng, Wolfgang Gries, Sami Selim. Biomarker of pyrethrum exposure. Toxicology letters. 2006 Apr; 162(2-3):195-201. doi: 10.1016/j.toxlet.2005.09.030. [PMID: 16257148]
  • Alec C Gerry, Xiaofei Zhang, Gabriele Leng, Allan D Inman, Robert I Krieger. Low pilot exposure to pyrethrin during ultra-low-volume (ULV) aerial insecticide application for control of adult mosquitoes. Journal of the American Mosquito Control Association. 2005 Sep; 21(3):291-5. doi: 10.2987/8756-971x(2005)21[291:lpetpd]2.0.co;2. [PMID: 16252519]
  • Ihsan Ergün, M Cenk Akbostanci, Başol Canbakan, Bilge Koçer, Arzu Ensari, Gökhan Nergizoglu, Kenan Keven. Minimal change nephrotic syndrome with stiff-person syndrome: is there a link?. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2005 Jul; 46(1):e11-4. doi: 10.1053/j.ajkd.2005.03.009. [PMID: 15983949]
  • L Elflein, E Berger-Preiss, A Preiss, M Elend, K Levsen, G Wünsch. Human biomonitoring of pyrethrum and pyrethroid insecticides used indoors: determination of the metabolites E-cis/trans-chrysanthemumdicarboxylic acid in human urine by gas chromatography-mass spectrometry with negative chemical ionization. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Oct; 795(2):195-207. doi: 10.1016/s1570-0232(03)00566-x. [PMID: 14522024]