Fraxinellone (BioDeep_00000314429)

 

Secondary id: BioDeep_00000229818

natural product PANOMIX_OTCML-2023


代谢物信息卡片


NCGC00385492-01_C14H16O3_(3R,3aR)-3-(3-Furyl)-3a,7-dimethyl-3a,4,5,6-tetrahydro-2-benzofuran-1(3H)-one

化学式: C14H16O3 (232.1099386)
中文名称: 梣酮
谱图信息: 最多检出来源 Viridiplantae(plant) 0.42%

分子结构信息

SMILES: CC/1=C/2C(=O)O[C@@H](C3=COC=C3)[C@]2(C)CCC1
InChI: InChI=1S/C14H16O3/c1-9-4-3-6-14(2)11(9)13(15)17-12(14)10-5-7-16-8-10/h5,7-8,12H,3-4,6H2,1-2H3/t12-,14+/m0/s1

描述信息

Fraxinellone is isolated from the root bark of the Rutaceae plant, Dictamnus dasycarpus. Fraxinellone is a PD-L1 inhibitor and inhibits HIF-1α protein synthesis without affecting HIF-1α protein degradation. Fraxinellone has the potential to be a valuable candidate for cancer treatment by targeting PD-L1[1].
Fraxinellone is isolated from the root bark of the Rutaceae plant, Dictamnus dasycarpus. Fraxinellone is a PD-L1 inhibitor and inhibits HIF-1α protein synthesis without affecting HIF-1α protein degradation. Fraxinellone has the potential to be a valuable candidate for cancer treatment by targeting PD-L1[1].
Fraxinellone is isolated from the root bark of the Rutaceae plant, Dictamnus dasycarpus. Fraxinellone is a PD-L1 inhibitor and inhibits HIF-1α protein synthesis without affecting HIF-1α protein degradation. Fraxinellone has the potential to be a valuable candidate for cancer treatment by targeting PD-L1[1].

同义名列表

10 个代谢物同义名

1(3H)-Isobenzofuranone, 3-(3-furanyl)-3a,4,5,6-tetrahydro-3a,7-dimethyl-, (3R-cis)- (9CI); (3R,3aR)-3-furan-3-yl-3a,7-dimethyl-3,4,5,6-tetrahydro-2-benzofuran-1-one; (3R,3aR)-3-(3-furyl)-3a,7-dimethyl-3,4,5,6-tetrahydroisobenzofuran-1-one; Phthalide, 3-(3-furyl)-3a,4,5,6-tetrahydro-3a,7-dimethyl-; Fraxinellone; NCI60_012928; ZINC00265490; 28808-62-0; NSC638730; NCGC00385492-01_C14H16O3_(3R,3aR)-3-(3-Furyl)-3a,7-dimethyl-3a,4,5,6-tetrahydro-2-benzofuran-1(3H)-one



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)

45 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

  • Shuting Wang, Jie Bao, Jie Li, Wanfang Li, Mengyin Tian, Caixia Qiu, Fei Pang, Xin Li, Jianbo Yang, Yuchi Hu, Sujuan Wang, Hongtao Jin. Fraxinellone Induces Hepatotoxicity in Zebrafish through Oxidative Stress and the Transporters Pathway. Molecules (Basel, Switzerland). 2022 Apr; 27(9):. doi: 10.3390/molecules27092647. [PMID: 35566003]
  • Bingfeng Zheng, Manman Yuan, Shenglan Wang, Yang Tan, Yizhu Xu, Jing Ye, Yanjie Gao, Xueqing Sun, Tianyi Wang, Lingdong Kong, Xingxin Wu, Qiang Xu. Fraxinellone alleviates kidney fibrosis by inhibiting CUG-binding protein 1-mediated fibroblast activation. Toxicology and applied pharmacology. 2021 06; 420(?):115530. doi: 10.1016/j.taap.2021.115530. [PMID: 33845055]
  • Min Lv, Suying Chen, Shaoyong Zhang, Hui Xu. Toxicology study of fraxinellone as ovicidal agents against Mythimna separata Walker and Bombyx mori Linaeus. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2020 Jul; 75(7-8):291-295. doi: 10.1515/znc-2020-0041. [PMID: 32568736]
  • Ji Lei, Xingxing Gou, Shaopeng Wei, Jinhong Zhou, Zongxiao Li. Spectroscopy, Thermodynamics and Molecular Docking of Fraxinellone with DNA. Bulletin of environmental contamination and toxicology. 2020 Jun; 104(6):864-870. doi: 10.1007/s00128-020-02860-7. [PMID: 32342111]
  • Yuanyuan Pei, Liang Chen, Yukun Huang, Jiahao Wang, Jingxian Feng, Minjun Xu, Yu Chen, Qingxiang Song, Gan Jiang, Xiao Gu, Qian Zhang, Xiaoling Gao, Jun Chen. Sequential Targeting TGF-β Signaling and KRAS Mutation Increases Therapeutic Efficacy in Pancreatic Cancer. Small (Weinheim an der Bergstrasse, Germany). 2019 06; 15(24):e1900631. doi: 10.1002/smll.201900631. [PMID: 31033217]
  • Qiongyin Fan, Baosheng Zhao, Chunguo Wang, Jingxuan Zhang, Jinying Wu, Ting Wang, Anlong Xu. Subchronic Toxicity Studies of Cortex Dictamni Extracts in Mice and Its Potential Hepatotoxicity Mechanisms in Vitro. Molecules (Basel, Switzerland). 2018 Sep; 23(10):. doi: 10.3390/molecules23102486. [PMID: 30274140]
  • Yue Xing, Chunliu Mi, Zhe Wang, Zhi Hong Zhang, Ming Yue Li, Hong Xiang Zuo, Jing Ying Wang, Xuejun Jin, Juan Ma. Fraxinellone has anticancer activity in vivo by inhibiting programmed cell death-ligand 1 expression by reducing hypoxia-inducible factor-1α and STAT3. Pharmacological research. 2018 09; 135(?):166-180. doi: 10.1016/j.phrs.2018.08.004. [PMID: 30103001]
  • Qin Li, Xiaobo Huang, Shaochen Li, Jingchun Ma, Min Lv, Hui Xu. Semisynthesis of Esters of Fraxinellone C4/10-Oxime and Their Pesticidal Activities. Journal of agricultural and food chemistry. 2016 Jul; 64(27):5472-8. doi: 10.1021/acs.jafc.6b01995. [PMID: 27338830]
  • Taijun Yin, Guanyi Yang, Yong Ma, Beibei Xu, Ming Hu, Ming You, Song Gao. Developing an activity and absorption-based quality control platform for Chinese traditional medicine: Application to Zeng-Sheng-Ping(Antitumor B). Journal of ethnopharmacology. 2015 Aug; 172(?):195-201. doi: 10.1016/j.jep.2015.06.019. [PMID: 26099633]
  • Min Lv, Wenjun Wu, Huixia Liu. Effects of Fraxinellone on the midgut enzyme activities of the 5th Instar Larvae of Oriental Armyworm, Mythimna separata walker. Toxins. 2014 Sep; 6(9):2708-18. doi: 10.3390/toxins6092708. [PMID: 25216084]
  • Pei Wang, Jianbo Sun, Enze Gao, Yunli Zhao, Wei Qu, Zhiguo Yu. Simultaneous determination of limonin, dictamnine, obacunone and fraxinellone in rat plasma by a validated UHPLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cortex Dictamni extract. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Jun; 928(?):44-51. doi: 10.1016/j.jchromb.2013.03.018. [PMID: 23611843]
  • Min Lü, Wenjun Wu, Huixia Liu. Insecticidal and feeding deterrent effects of fraxinellone from Dictamnus dasycarpus against four major pests. Molecules (Basel, Switzerland). 2013 Mar; 18(3):2754-62. doi: 10.3390/molecules18032754. [PMID: 23455666]
  • Sen Wang, Shuiping Ou, Yongmei Guan, Dezhi Wu, Lihua Chen, Weifeng Zhu. [Dermatopharmacokinetic studies of liangfu cream in mice skin]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Sep; 35(17):2254-7. doi: 10.4268/cjcmm20101707. [PMID: 21137331]
  • Sen Wang, Weifeng Zhu, Shuiping Ou, Yongmeii Guan, Lihua Chen, Ming Yang. [Effects of penetration enhancers on in vitro percutaneous absorption and amount retained in skin of paeonol, dictamnine, fraxinellone and glycyrrhetinic acid in Liangfu cream]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Jul; 34(14):1778-82. doi: . [PMID: 19894505]
  • Jong-Hwan Kim, Young-Mi Park, Ji-Sun Shin, Seung Jae Park, Jung-Hye Choi, Hyun-Ju Jung, Hee-Juhn Park, Kyung-Tae Lee. Fraxinellone inhibits lipopolysaccharide-induced inducible nitric oxide synthase and cyclooxygenase-2 expression by negatively regulating nuclear factor-kappa B in RAW 264.7 macrophages cells. Biological & pharmaceutical bulletin. 2009 Jun; 32(6):1062-8. doi: 10.1248/bpb.32.1062. [PMID: 19483316]
  • Jeong Seon Yoon, Sang Hyun Sung, Young Choong Kim. Neuroprotective limonoids of root bark of Dictamnus dasycarpus. Journal of natural products. 2008 Feb; 71(2):208-11. doi: 10.1021/np070588o. [PMID: 18198838]
  • Qi-Qiong Ran, Li-Ping Ruan, Dan-Ni Zhu, Bo-Yang Yu. [Improving the solubility of fraxinellone to increase its oral bioavailability and hepatoprotective action against acute liver injury in mice]. Yao xue xue bao = Acta pharmaceutica Sinica. 2007 Jun; 42(6):675-80. doi: ". [PMID: 17702408]
  • Chun-lan Yuan, De-suo Yang. [Determination of fraxinellone in root bark of Dictamnus dasycarpus by RP-HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Jun; 31(12):992-4. doi: ". [PMID: 17048647]
  • R-L Yang, T-L Jia, R-Q Zhang. Microbial transformation of fraxinellone by Aspergillus niger. Journal of Asian natural products research. 2005 Dec; 7(6):843-5. doi: 10.1080/10286020310001653318. [PMID: 16308202]
  • Zhi Long Liu, Yuan Jian Xu, Jien Wu, Swee Hock Goh, Shuit Hung Ho. Feeding deterrents from Dictamnus dasycarpus Turcz against two stored-product insects. Journal of agricultural and food chemistry. 2002 Mar; 50(6):1447-50. doi: 10.1021/jf010838l. [PMID: 11879018]