4-Hydroxy-2-butenoic acid gamma-lactone (BioDeep_00000011778)

 

Secondary id: BioDeep_00001867703

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2-Butenoic acid, 4-hydroxy-, laquo gammaraquo -lactone

化学式: C4H4O2 (84.0211284)
中文名称: 2（5H）-呋喃酮, 2(5H)-呋喃酮
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 4.08%

分子结构信息

SMILES: C1=CC(=O)OC1
InChI: InChI=1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2

描述信息

4-Hydroxy-2-butenoic acid gamma-lactone is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]")
D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents
D019440 - Anti-Obesity Agents > D001067 - Appetite Depressants
2(5H)-Furanone is an endogenous metabolite.

同义名列表

55 个代谢物同义名

2-Butenoic acid, 4-hydroxy-, laquo gammaraquo -lactone; Crotonic acid, 4-hydroxy-, laquo gammaraquo -lactone; 4-Hydroxy-2-butenoic acid laquo gammaraquo -lactone; Crotonic acid, 4-hydroxy-, gamma-lactone (6ci,7ci); 2(5H)-Furanone (laquo gammaraquo -crotonolactone); Laquo gammaraquo -hydroxycrotonic acid lactone; 2-Butenoic acid, 4-hydroxy-, gamma-lactone; 2-Butenoic acid-laquo gammaraquo -lactone; 4-Hydroxy-2-butenoic acid gamma-lactone; Laquo deltaraquo ,alpha,beta-butenolide; 2-oxo-2,5-Dihydrofuran(2-[5H]-furanone); 4-Hydroxycrotonic acid gamma-lactone; 4-Hydroxy-2-butenoic acid g-lactone; 4-Hydroxy-2-butenoate gamma-lactone; 4-Hydroxy-2-butenoic acid γ-lactone; gamma-Hydroxycrotonic acid lactone; 4-Hydroxy-2-butenoic acid lactone; Laquo gammaraquo -crotonolactone; 4-Hydroxy-2-butenoate g-lactone; 4-Hydroxy-2-butenoate γ-lactone; Γ-hydroxycrotonic acid lactone; g-Hydroxycrotonic acid lactone; gamma-Hydroxycrotonate lactone; Laquo gammaraquo -crotolactone; 2-Butenoic acid-gamma-lactone; 4-Hydroxy-2-butenoate lactone; 2-Butenoic acid gamma-lactone; delta,alpha,beta-Butenolide; Γ-hydroxycrotonate lactone; g-Hydroxycrotonate lactone; alpha,alpha,beta-Butolide; alpha,beta-Crotonolactone; 2,5-dihydrofuran-2-one; 2-oxo-2,5-Dihydrofuran; gamma-Crotonolactone; gamma-Crotolactone; Α,β-crotonolactone; a,b-Crotonolactone; 2-Buten-1,4-olide; Isocrotonolactone; Γ-crotonolactone; g-Crotonolactone; 5 H-Furan-2-one; Furan-2(5H)-one; 2-(5H)-Furanone; 2-Buten-4-olide; Crotonolactone; 5H-Furan-2-one; 2(5H)-Furanone; 2-Butenolide; 2-Furanone; Butenolide; 2-b4O; 2(5H)-Furanone; 2(5H)-Furanone



数据库引用编号

18 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)

5 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

  • Qinghe Zhang, Juan Tang, Bingli Gao, Cheng Qu, Jinda Wang, Chen Luo, Ran Wang. Overexpression of CYP6CX4 contributing to field-evolved resistance to flupyradifurone, one novel butenolide insecticide, in Bemisia tabaci from China. International journal of biological macromolecules. 2024 Apr; 265(Pt 2):131056. doi: 10.1016/j.ijbiomac.2024.131056. [PMID: 38522686]
  • Renxuan Zou, Xiang Li, Xi Jiang, Dongmei Shi, Qing Han, Hongxia Duan, Qing Yang. Novel Butenolide Derivatives as Dual-Chitinase Inhibitors to Arrest the Growth and Development of the Asian Corn Borer. Journal of agricultural and food chemistry. 2024 Mar; 72(9):5036-5046. doi: 10.1021/acs.jafc.3c06714. [PMID: 38377548]
  • Yufeng Jiang, Jiule Wang, Hua Zhang, Xuelu Tian, Zhiqiang Liang, Xinli Xu, Jie Bao, Biao Chen. Biological Activity and Sterilization Mechanism of Marine Fungi-derived Aromatic Butenolide Asperbutenolide A Against Staphylococcus aureus. Chemistry & biodiversity. 2024 Feb; 21(2):e202301826. doi: 10.1002/cbdv.202301826. [PMID: 38155523]
  • Kim T Melville, Muhammad Kamran, Jiaren Yao, Marianne Costa, Madeleine Holland, Nicolas L Taylor, Georg Fritz, Gavin R Flematti, Mark T Waters. Perception of butenolides by Bacillus subtilis via the α/β hydrolase RsbQ. Current biology : CB. 2023 Dec; ?(?):. doi: 10.1016/j.cub.2023.12.035. [PMID: 38183985]
  • Wei Wang, Kang-Wen Xu, Mei Wang, Peng Wu, Zi-Ru Zhang, Xi Gao, Yi-Qiang Li, Guo-Xing Wu, Cheng-Sheng Zhang, Dong-Lin Zhao. Phytotoxic and Antimicrobial Terrein Derivatives and Butenolides Isolated from the Endophytic Fungus Aspergillus terreus HT5. Journal of agricultural and food chemistry. 2023 Dec; 71(51):20713-20723. doi: 10.1021/acs.jafc.3c05955. [PMID: 38095326]
  • Muhammad Kamran, Kim T Melville, Mark T Waters. Karrikin signalling: impacts on plant development and abiotic stress tolerance. Journal of experimental botany. 2023 Nov; ?(?):. doi: 10.1093/jxb/erad476. [PMID: 38001035]
  • Seham S El-Hawary, Abeer S Moawad, Hebatallah S Bahr, Eman Z Attia, Mo Men H El-Katatny, Muhamad Mustafa, Ahmed A Al-Karmalawy, Mostafa E Rateb, Jian-Ye Zhang, Usama Ramadan Abdelmohsen, Rabab Mohammed. Promising Cytotoxic butenolides from the Soybean endophytic fungus Aspergillus terreus: a combined molecular docking and in-vitro studies. Journal of applied microbiology. 2023 Jul; ?(?):. doi: 10.1093/jambio/lxad129. [PMID: 37401132]
  • Yihao Li, Tingting Zhang, Haoyun Ma, Leichuan Xu, Qian Zhang, Lei He, Jiazhen Jiang, Zhenhua Zhang, Zhangwu Zhao, Mingan Wang. Design, Synthesis, and Antifungal/Antioomycete Activity of Thiohydantoin Analogues Containing Spirocyclic Butenolide. Journal of agricultural and food chemistry. 2023 Apr; 71(16):6249-6267. doi: 10.1021/acs.jafc.2c09144. [PMID: 37058604]
  • Jiming Chen, Diwakar Shukla. Effect of Histidine Covalent Modification on Strigolactone Receptor Activation and Selectivity. Biophysical journal. 2023 Feb; ?(?):. doi: 10.1016/j.bpj.2023.02.012. [PMID: 36798027]
  • Yun-Fei Ai, Shu-Hui Dong, Bin Lin, Xiao-Xiao Huang, Shao-Jiang Song. Acylated sucroses and butenolide analog from the leaves of Tripterygium wilfordii Hook. f. and their potential anti-tyrosinase effects. Fitoterapia. 2022 Sep; 161(?):105250. doi: 10.1016/j.fitote.2022.105250. [PMID: 35798062]
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  • Jie Bao, Xiu-Xiu Li, Kongkai Zhu, Fei He, Yin-Yin Wang, Jin-Hai Yu, Xiaoyong Zhang, Hua Zhang. Bioactive aromatic butenolides from a mangrove sediment originated fungal species, Aspergillus terreus SCAU011. Fitoterapia. 2021 Apr; 150(?):104856. doi: 10.1016/j.fitote.2021.104856. [PMID: 33582267]
  • Zhenya Wang, Jieyu Fang, Jiao Luo, Duoduo Hou, Yayun Tan, Zichen Gu, Yongzhuang Ge, Lu Mao, Luyang Liu, Hongmin Liu, Zhanyong Wei, Haiwei Xu. Antiviral Activity of 3D, a Butene Lactone Derivative Against Influenza A Virus In Vitro and In Vivo. Viruses. 2021 02; 13(2):. doi: 10.3390/v13020278. [PMID: 33670217]
  • Martin Klapper, Kevin Schlabach, André Paschold, Shuaibing Zhang, Somak Chowdhury, Klaus-Dieter Menzel, Miriam A Rosenbaum, Pierre Stallforth. Biosynthesis of Pseudomonas-Derived Butenolides. Angewandte Chemie (International ed. in English). 2020 03; 59(14):5607-5610. doi: 10.1002/anie.201914154. [PMID: 31880848]
  • Tao Yang, Yuke Lian, Chongying Wang. Comparing and Contrasting the Multiple Roles of Butenolide Plant Growth Regulators: Strigolactones and Karrikins in Plant Development and Adaptation to Abiotic Stresses. International journal of molecular sciences. 2019 Dec; 20(24):. doi: 10.3390/ijms20246270. [PMID: 31842355]
  • Ping-Chen Tu, Han-Chun Tseng, Yu-Chia Liang, Guan-Jhong Huang, Te-Ling Lu, Tzong-Fu Kuo, Yueh-Hsiung Kuo. Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives. Molecules (Basel, Switzerland). 2019 Sep; 24(18):. doi: 10.3390/molecules24183336. [PMID: 31540241]
  • Devashan Naidoo, Martin Pošta, Ayan Roy, Manoj Kulkarni, Johannes Van Staden. Synthesis of potent neuroprotective butenolides based on plant smoke derived 3,4,5-Trimethylfuran-2(5H)-one and 3-methyl-2H-furo[2,3-c]pyrone-2-one. Phytochemistry. 2019 Jul; 163(?):187-194. doi: 10.1016/j.phytochem.2019.03.014. [PMID: 31014820]
  • Ji-Wen Sheng, Dong-Mei Liu, Liang Jing, Gui-Xue Xia, Wei-Fen Zhang, Jing-Ru Jiang, Jin-Bao Tang. Striatisporolide A, a butenolide metabolite from Athyrium multidentatum (Doll.) Ching, as a potential antibacterial agent. Molecular medicine reports. 2019 Jul; 20(1):198-204. doi: 10.3892/mmr.2019.10244. [PMID: 31115578]
  • Stéphanie M Swarbreck, Yannick Guerringue, Elsa Matthus, Fiona J C Jamieson, Julia M Davies. Impairment in karrikin but not strigolactone sensing enhances root skewing in Arabidopsis thaliana. The Plant journal : for cell and molecular biology. 2019 05; 98(4):607-621. doi: 10.1111/tpj.14233. [PMID: 30659713]
  • Ping-Zhuo Liang, Kang-Sheng Ma, Xue-Wei Chen, Chun-Yan Tang, Jin Xia, Hsin Chi, Xi-Wu Gao. Toxicity and Sublethal Effects of Flupyradifurone, a Novel Butenolide Insecticide, on the Development and Fecundity of Aphis gossypii (Hemiptera: Aphididae). Journal of economic entomology. 2019 03; 112(2):852-858. doi: 10.1093/jee/toy381. [PMID: 30590572]
  • Geanne A Alves Conserva, Thais A da Costa-Silva, Maiara Amaral, Guilherme M Antar, Bruno J Neves, Carolina H Andrade, Andre G Tempone, João Henrique G Lago. Butenolides from Nectandra oppositifolia (Lauraceae) displayed anti-Trypanosoma cruzi activity via deregulation of mitochondria. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Feb; 54(?):302-307. doi: 10.1016/j.phymed.2018.09.236. [PMID: 30668381]
  • Guangfeng Liao, Ping Wu, Jinghua Xue, Lan Liu, Hanxiang Li, Xiaoyi Wei. Asperimides A-D, anti-inflammatory aromatic butenolides from a tropical endophytic fungus Aspergillus terreus. Fitoterapia. 2018 Nov; 131(?):50-54. doi: 10.1016/j.fitote.2018.10.011. [PMID: 30308231]
  • Changxing Qi, Weixi Gao, Jianping Wang, Mengting Liu, Jinwen Zhang, Chunmei Chen, Zhengxi Hu, Yongbo Xue, Dongyan Li, Qing Zhang, Yongji Lai, Qun Zhou, Hucheng Zhu, Yonghui Zhang. Terrusnolides A-D, new butenolides with anti-inflammatory activities from an endophytic Aspergillus from Tripterygium wilfordii. Fitoterapia. 2018 Oct; 130(?):134-139. doi: 10.1016/j.fitote.2018.08.021. [PMID: 30165179]
  • Agnieszka Płażek, Franciszek Dubert, Przemysław Kopeć, Michał Dziurka, Agnieszka Kalandyk, Jakub Pastuszak, Piotr Waligórski, Bogdan Wolko. Long-Term Effects of Cold on Growth, Development and Yield of Narrow-Leaf Lupine May Be Alleviated by Seed Hydropriming or Butenolide. International journal of molecular sciences. 2018 Aug; 19(8):. doi: 10.3390/ijms19082416. [PMID: 30115849]
  • Misa Yamauchi, Kotomi Ueno, Toshio Furumoto, Takatoshi Wakabayashi, Masaharu Mizutani, Hirosato Takikawa, Yukihiro Sugimoto. Stereospecific reduction of the butenolide in strigolactones in plants. Bioorganic & medicinal chemistry. 2018 08; 26(14):4225-4233. doi: 10.1016/j.bmc.2018.07.016. [PMID: 30007566]
  • Genzoh Tanabe, Yoshiaki Manse, Teppei Ogawa, Naoki Sonoda, Shinsuke Marumoto, Fumihiro Ishikawa, Kiyofumi Ninomiya, Saowanee Chaipech, Yutana Pongpiriyadacha, Osamu Muraoka, Toshio Morikawa. Total Synthesis of γ-Alkylidenebutenolides, Potent Melanogenesis Inhibitors from Thai Medicinal Plant Melodorum fruticosum. The Journal of organic chemistry. 2018 08; 83(15):8250-8264. doi: 10.1021/acs.joc.8b00986. [PMID: 29972303]
  • Fangfang Li, Daiwei Chen, Shengsheng Lu, Guang Yang, Xiaoling Zhang, Zhao Chen, Sheng Fan, Shaohua Wu, Jian He. Anti-Influenza A Viral Butenolide from Streptomyces sp. Smu03 Inhabiting the Intestine of Elephas maximus. Viruses. 2018 07; 10(7):. doi: 10.3390/v10070356. [PMID: 29976861]
  • Xu Pang, Jian-Yuan Zhao, Xiao-Mei Fang, Tao Zhang, De-Wu Zhang, Hong-Yu Liu, Jing Su, Shan Cen, Li-Yan Yu. Metabolites from the Plant Endophytic Fungus Aspergillus sp. CPCC 400735 and Their Anti-HIV Activities. Journal of natural products. 2017 10; 80(10):2595-2601. doi: 10.1021/acs.jnatprod.6b00878. [PMID: 29016131]
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  • Alexandre de Saint Germain, Guillaume Clavé, Marie-Ange Badet-Denisot, Jean-Paul Pillot, David Cornu, Jean-Pierre Le Caer, Marco Burger, Frank Pelissier, Pascal Retailleau, Colin Turnbull, Sandrine Bonhomme, Joanne Chory, Catherine Rameau, François-Didier Boyer. An histidine covalent receptor and butenolide complex mediates strigolactone perception. Nature chemical biology. 2016 10; 12(10):787-794. doi: 10.1038/nchembio.2147. [PMID: 27479744]
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