Daminozide (BioDeep_00000017453)

Main id: BioDeep_00000002339

 

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


2,2-Dimethylhydrazid kyseliny jantarove [Czech]

化学式: C6H12N2O3 (160.0847882)
中文名称: 甲醇中丁酰肼溶液, 丁酰肼
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN(C)NC(=O)CCC(=O)O
InChI: InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11)

描述信息

Succinic acid 2,2-dimethylhydrazide appears as odorless white crystals or powder. (NTP, 1992)
Daminozide is a straight-chain fatty acid.
Daminozide — also known as Alar, Kylar, B-NINE, DMASA, SADH, or B 995 — is a plant growth regulator, a chemical sprayed on fruit to regulate their growth, make their harvest easier, and keep apples from falling off the trees before they are ripe. This makes sure they are red and firm for storage. Alar was first approved for use in the U.S. in 1963, it was primarily used on apples until 1989 when it was voluntarily withdrawn by the manufacturer after the U.S. Environmental Protection Agency proposed banning it based on unacceptably high cancer risks to consumers.
D006133 - Growth Substances > D010937 - Plant Growth Regulators
D010575 - Pesticides > D006540 - Herbicides
D016573 - Agrochemicals
Daminozide, a plant growth regulator, is a selective inhibitor of the human KDM2/7 histone demethylases, with IC50s of 0.55, 1.5 and 2.1 μM for PHF8, KDM2A, and KIAA1718, respectively. Daminozide has >100-fold selectivity for KDM2/7 subfamily versus other demethylase subfamily members tested[1][2].

同义名列表

57 个代谢物同义名

2,2-Dimethylhydrazid kyseliny jantarove [Czech]; 3-(N,N-dimethylhydrazinecarbonyl)propanoic acid; butanedioic acid, mono (2,2-dimethylhydrazide); 4-(2,2-Dimethylhydrazino)-4-oxobutanoic acid #; 4-(2,2-dimethylhydrazino)-4-oxo-butanoic acid; 4-(2,2-dimethylhydrazinyl)-4-oxobutanoic acid; Butanedioic acid, mono(2,2-dimethylhydrazide); Bernsteinsaeure-2,2-dimethylhydrazid [German]; Butanedioic acid mono(2,2-dimethylhydrazide); Daminozide, PESTANAL(R), analytical standard; 4-(2,2-Dimethylhydrazino)-4-oxobutanoic acid; Butanedioic acid, 1-(2,2-dimethylhydrazide); N-Dimethylamino-beta-carbamylpropionic acid; Succinic acid, mono(2,2-dimethylhydrazide); 1-(2,2-Dimethylhydrazide)butanedioi c acid; 1-(2,2-Dimethylhydrazide)butanedioic acid; N-Dimethylamino-succinamidsaeure [German]; Succinic acid, mono-2,2-dimethylhydrazine; 2,2-Dimethylhydrazid kyseliny jantarove; succinic acid, 2,2-dimethyl hydrazide; SUCCINIC ACID, 2,2-DIMETHYLHYDRAZIDE; Succinic Acid, N,N-dimethylhydrazide; Bernsteinsaeure-2,2-dimethylhydrazid; Succinic acid-2,2-dimethylhydrazide; Succinic acid 2,2-dimethylhydrazide; 2,2-DIMETHYLHYDRAZINE SUCCINIC ACID; Succinic acid N,N-dimethylhydrazide; N-(dimethylamino)succinamic acid; N-Dimethylamino-succinamidsaeure; Succinic 1,1-dimethyl hydrazide; Succinic N,N-dimethylhydrazide; Dimethylaminosuccinamic acid; NOQGZXFMHARMLW-UHFFFAOYSA-N; Daminozide [ANSI:BSI:ISO]; DAMINOZIDE [HSDB]; Daminozide [ISO]; DAMINOZIDE [MI]; UNII-F6KF33M5UB; Tox21_300919; B9 regulator; Tox21_202199; Daminozide; F6KF33M5UB; Aminozide; C6H12N2O3; AI3-50727; Aminozid; Alar-85; Alar 85; Dazide; B-Nine; Kylar; Dimas; DMASA; DYaK; SADH; ALAR



数据库引用编号

11 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)

2 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

  • Debasmita Das, Morium Begum, Pallab Paul, Ishita Dutta, Sayarneel Mandal, Papiya Ghosh, Sujay Ghosh. Effects of plant growth retardant daminozide (Alar) on neuromuscular co-ordination behavior in Drosophila melanogaster. Journal of toxicology and environmental health. Part A. 2022 Nov; 85(22):921-936. doi: 10.1080/15287394.2022.2114564. [PMID: 35996764]
  • 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]
  • Sohini Singha Roy, Sujay Ghosh. Genes regulating wing patterning in Drosophila melanogaster show reduced expression under exposure of Daminozide, the fruit ripening retardant. Environmental toxicology and pharmacology. 2020 Apr; 75(?):103322. doi: 10.1016/j.etap.2019.103322. [PMID: 31877500]
  • 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]
  • Mojtaba Karimi, Javad Hashemi, Ali Ahmadi, Alireza Abbasi, Antonio Pompeiano, Silvia Tavarini, Lorenzo Guglielminetti, Luciana G Angelini. Opposing effects of external gibberellin and Daminozide on Stevia growth and metabolites. Applied biochemistry and biotechnology. 2015 Jan; 175(2):780-91. doi: 10.1007/s12010-014-1310-7. [PMID: 25342260]
  • Fang fei Liu, Ying Yu, Bi xia Lin, Xiao gang Hu, Yu juan Cao, Jian zhong Wu. Visualization of hormone binding proteins in vivo based on Mn-doped CdTe QDs. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2014 Oct; 131(?):9-16. doi: 10.1016/j.saa.2014.04.066. [PMID: 24815196]
  • Nathan R Rose, Esther C Y Woon, Anthony Tumber, Louise J Walport, Rasheduzzaman Chowdhury, Xuan Shirley Li, Oliver N F King, Clarisse Lejeune, Stanley S Ng, Tobias Krojer, Mun Chiang Chan, Anna M Rydzik, Richard J Hopkinson, Ka Hing Che, Michelle Daniel, Claire Strain-Damerell, Carina Gileadi, Grazyna Kochan, Ivanhoe K H Leung, James Dunford, Kar Kheng Yeoh, Peter J Ratcliffe, Nicola Burgess-Brown, Frank von Delft, Susanne Muller, Brian Marsden, Paul E Brennan, Michael A McDonough, Udo Oppermann, Robert J Klose, Christopher J Schofield, Akane Kawamura. Plant growth regulator daminozide is a selective inhibitor of human KDM2/7 histone demethylases. Journal of medicinal chemistry. 2012 Jul; 55(14):6639-43. doi: 10.1021/jm300677j. [PMID: 22724510]
  • Dasharath P Oulkar, Kaushik Banerjee, Sunil Kulkarni. Multiresidue analysis of plant growth regulators in grapes by triple quadrupole and quadrupole-time of flight-based liquid chromatography/mass spectrometry. Journal of AOAC International. 2011 Nov; 94(6):1715-21. doi: 10.5740/jaoacint.sgeoulkar. [PMID: 22320078]
  • Mónica Meijón, María Jesús Cañal, Luis Valledor, Roberto Rodríguez, Isabel Feito. Epigenetic and physiological effects of gibberellin inhibitors and chemical pruners on the floral transition of azalea. Physiologia plantarum. 2011 Mar; 141(3):276-88. doi: 10.1111/j.1399-3054.2010.01430.x. [PMID: 21077902]
  • Corinna Schmiderer, Sabine Grausgruber-Gröger, Paolo Grassi, Ralf Steinborn, Johannes Novak. Influence of gibberellin and daminozide on the expression of terpene synthases and on monoterpenes in common sage (Salvia officinalis). Journal of plant physiology. 2010 Jul; 167(10):779-86. doi: 10.1016/j.jplph.2009.12.009. [PMID: 20163890]
  • Julia C Engelmann, Rosalia Deeken, Tobias Müller, Günter Nimtz, M Rob G Roelfsema, Rainer Hedrich. Is gene activity in plant cells affected by UMTS-irradiation? A whole genome approach. Advances and applications in bioinformatics and chemistry : AABC. 2008; 1(?):71-83. doi: 10.2147/aabc.s3570. [PMID: 21918607]
  • Gerald S Pullman, J Mein, S Johnson, Y Zhang. Gibberellin inhibitors improve embryogenic tissue initiation in conifers. Plant cell reports. 2005 Feb; 23(9):596-605. doi: 10.1007/s00299-004-0880-1. [PMID: 15688237]
  • Ching-Hua Huang, Alan T Stone. Transformation of the plant growth regulator daminozide (Alar) and structurally related compounds with CuII ions: oxidation versus hydrolysis. Environmental science & technology. 2003 May; 37(9):1829-37. doi: 10.1021/es026244w. [PMID: 12775054]
  • C Bicchi, C Cordero, P Rubiolo, A Occelli. Determination of daminozide residues in apple pulp using HPLC-DAD-UV. Journal of agricultural and food chemistry. 2001 Aug; 49(8):3548-52. doi: 10.1021/jf0103673. [PMID: 11513626]
  • B J Rosenberg, E M Barbeau, R Moure-Eraso, C Levenstein. The work environment impact assessment: a methodologic framework for evaluating health-based interventions. American journal of industrial medicine. 2001 Feb; 39(2):218-26. doi: 10.1002/1097-0274(200102)39:2<218::aid-ajim1009>3.0.co;2-4. [PMID: 11170164]
  • L Mott. Alar again: science, the media, and the public's right to know. International journal of occupational and environmental health. 2000 Jan; 6(1):68-70. doi: 10.1179/oeh.2000.6.1.68. [PMID: 10691344]
  • H G Mol, R C van Dam, R J Vreeken, O M Steijger. Determination of daminozide in apples and apple leaves by liquid chromatography--mass spectrometry. Journal of chromatography. A. 1999 Feb; 833(1):53-60. doi: 10.1016/s0021-9673(98)00915-7. [PMID: 10074699]
  • I Rahden-Staroń, M Szumiło, P Ziemkiewicz, T Szymczyk-Wasiluk. Daminozide--lack of the genotoxic activity in the short-term bacterial tests. Roczniki Panstwowego Zakladu Higieny. 1997; 48(2):111-7. doi: ". [PMID: 9306721]
  • A M Finkel. Toward less misleading comparisons of uncertain risks: the example of aflatoxin and alar. Environmental health perspectives. 1995 Apr; 103(4):376-85. doi: 10.1289/ehp.95103376. [PMID: 7607139]
  • R Cabral, K Hakoi, T Hoshiya, R Hasegawa, N Ito. Lack of carcinogenicity of daminozide, alone or in combination with its contaminant 1,1-dimethylhydrazine, in a medium-term bioassay. Teratogenesis, carcinogenesis, and mutagenesis. 1995 199; 15(6):307-12. doi: 10.1002/(sici)1520-6866(1996)15:6<307::aid-tcm6>3.0.co;2-m. [PMID: 8732881]
  • M J Mattina, H M Pylypiw, A A Paiva. Daminozide residues in apple orchards: concentrations in fruit, trees, and soil. Bulletin of environmental contamination and toxicology. 1990 Dec; 45(6):858-63. doi: 10.1007/bf01701084. [PMID: 2279135]
  • E C Bonard. [Carcinogens]. Revue medicale de la Suisse romande. 1989 Oct; 109(10):841-2. doi: ". [PMID: 2814134]
  • E Groth. Alar in apples. Science (New York, N.Y.). 1989 May; 244(4906):755. doi: 10.1126/science.2727678. [PMID: 2727678]
  • B N Ames, L S Gold. Pesticides, risk, and applesauce. Science (New York, N.Y.). 1989 May; 244(4906):755-7. doi: 10.1126/science.2727679. [PMID: 2727679]
  • T H Jukes. Alar and apples. Science (New York, N.Y.). 1989 May; 244(4904):515. doi: ". [PMID: 2717938]
  • P Sagelsdorff, W K Lutz, C Schlatter. DNA methylation in rat liver by daminozide, 1,1-dimethylhydrazine, and dimethylnitrosamine. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1988 Nov; 11(4):723-30. doi: 10.1016/0272-0590(88)90135-2. [PMID: 3229594]
  • A O Koshkarian, E S Kocharian, G A Aloian, A Kh Avakian. [Effect of plant growth regulators, hydrazine derivatives, on the state of the microsomal systems of the liver]. Biulleten' eksperimental'noi biologii i meditsiny. 1988 Jul; 106(7):40-2. doi: . [PMID: 3401574]
  • N Zou. [Effect of B9 on the chemical components of Panax ginseng]. Zhong yao tong bao (Beijing, China : 1981). 1986 Dec; 11(12):8-9. doi: ". [PMID: 2952345]
  • S Gabr, A Sharaf, S el-Saadany. Effect of chlormequat and alar on some biochemical constituents in tomato plants and fruits. Die Nahrung. 1985; 29(3):219-28. doi: 10.1002/food.19850290302. [PMID: 4000246]
  • A Kh Avakian, A D Marukhian. [Alar metabolism in the rat liver]. Farmakologiia i toksikologiia. 1982 Jul; 45(4):81-3. doi: ". [PMID: 7128795]
  • W H Newsome. Determination of daminozide residues on foods and its degradation to 1,1-dimethylhydrazine by cooking. Journal of agricultural and food chemistry. 1980 Mar; 28(2):319-21. doi: 10.1021/jf60228a042. [PMID: 7391369]
  • B D Ripley, E C Lougheed, S R Miller. Daminozide residues on orchard-treated apples. Journal of agricultural and food chemistry. 1979 Nov; 27(6):1389-91. doi: 10.1021/jf60226a047. [PMID: 544670]
  • J M Bonga. Organogenesis in in vitro cultures of embryonic shoots of Abies balsamea (balsam fir). In vitro. 1977 Jan; 13(1):41-8. doi: 10.1007/bf02615503. [PMID: 856724]