Bavachinin (BioDeep_00000229994)

 

Secondary id: BioDeep_00000176450, BioDeep_00000402846

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


4H-1-Benzopyran-4-one, 2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-, (2S)-

化学式: C21H22O4 (338.1518012)
中文名称: 补骨脂二氢黄酮甲醚, 补骨脂双氢黄酮甲醚, 甲基补骨脂黄酮A
谱图信息: 最多检出来源 Viridiplantae(plant) 33.33%

分子结构信息

SMILES: C1(OC)=CC2OC(C3C=CC(O)=CC=3)CC(=O)C=2C=C1C/C=C(/C)\C
InChI: InChI=1S/C21H22O4/c1-13(2)4-5-15-10-17-18(23)11-20(14-6-8-16(22)9-7-14)25-21(17)12-19(15)24-3/h4,6-10,12,20,22H,5,11H2,1-3H3

描述信息

Bavachinin is a member of flavanones.
Bavachinin is a natural product found in Cullen corylifolium with data available.
See also: Cullen corylifolium fruit (part of).
Bavachinin is agonist of pan-peroxisome proliferator-activated receptor (PPAR), with the IC50 value of 21.043 μM, 12.819 μM, and 0.622 μM to PPAR-α, RRAR-β/δ, and PPAR-γ, respectively. Bavachinin is an inhibitor of HIF-1α. Bavachinin exhibits antitumor activity against non-small cell lung cancer by targeting RRAR-γ. Bavachinin is a natural compound with anti-inflammatory and anti-angiogenic activities. Bavachinin has orally bioactivity.[1][2][3][4][5].
Bavachinin is agonist of pan-peroxisome proliferator-activated receptor (PPAR), with the IC50 value of 21.043 μM, 12.819 μM, and 0.622 μM to PPAR-α, RRAR-β/δ, and PPAR-γ, respectively. Bavachinin is an inhibitor of HIF-1α. Bavachinin exhibits antitumor activity against non-small cell lung cancer by targeting RRAR-γ. Bavachinin is a natural compound with anti-inflammatory and anti-angiogenic activities. Bavachinin has orally bioactivity.[1][2][3][4][5].
Bavachinin is agonist of pan-peroxisome proliferator-activated receptor (PPAR), with the IC50 value of 21.043 μM, 12.819 μM, and 0.622 μM to PPAR-α, RRAR-β/δ, and PPAR-γ, respectively. Bavachinin is an inhibitor of HIF-1α. Bavachinin exhibits antitumor activity against non-small cell lung cancer by targeting RRAR-γ. Bavachinin is a natural compound with anti-inflammatory and anti-angiogenic activities. Bavachinin has orally bioactivity.[1][2][3][4][5].
Bavachinin is agonist of pan-peroxisome proliferator-activated receptor (PPAR), with the IC50 value of 21.043 μM, 12.819 μM, and 0.622 μM to PPAR-α, RRAR-β/δ, and PPAR-γ, respectively. Bavachinin is an inhibitor of HIF-1α. Bavachinin exhibits antitumor activity against non-small cell lung cancer by targeting RRAR-γ. Bavachinin is a natural compound with anti-inflammatory and anti-angiogenic activities. Bavachinin has orally bioactivity.[1][2][3][4][5].

同义名列表

16 个代谢物同义名

4H-1-Benzopyran-4-one, 2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-, (2S)-; (2S)-2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one; 4H-1-Benzopyran-4-one, 2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-butenyl)-, (S)-; (2S)-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one; (S)-2-(4-Hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)chroman-4-one; Flavanone, 4-hydroxy-7-methoxy-6-(3-methyl-2-butenyl)-; 4-hydroxy-7-methoxy-6-(3-methyl-2-butenyl)flavanone; 5-18-04-00132 (Beilstein Handbook Reference); 4-Hydroxy-7-methoxy-6-prenylflavanone; Bavachinin, >=95\\% (LC/MS-ELSD); 7-O-methylbavachin; UNII-VL3EV483SZ; bavachinin A; Bavachinin; VL3EV483SZ; (S) -2,3-Dihydro-2- (4-hydroxyphenyl) -7-methoxy-6- (3-methyl-2-butenyl) -4H-1-benzopyran-4-one



数据库引用编号

14 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)

16 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

  • Xi Dong, Shan Lu, Yu Tian, Han Ma, Yang Wang, Xuelian Zhang, Guibo Sun, Yun Luo, Xiaobo Sun. Bavachinin Protects the Liver in NAFLD by Promoting Regeneration via Targeting PCNA. Journal of advanced research. 2023 Feb; ?(?):. doi: 10.1016/j.jare.2023.02.007. [PMID: 36801384]
  • Wen Zhang, Jingwen Liu, Yiming Li, Fujiang Guo. A bavachinin analog, D36, induces cell death by targeting both autophagy and apoptosis pathway in acute myeloid leukemia cells. Cancer chemotherapy and pharmacology. 2022 09; 90(3):251-265. doi: 10.1007/s00280-022-04462-y. [PMID: 35960342]
  • Jih-Tung Pai, Ming-Wei Hsu, Yann-Lii Leu, Kuo-Ting Chang, Meng-Shih Weng. Induction of G2/M Cell Cycle Arrest via p38/p21Waf1/Cip1-Dependent Signaling Pathway Activation by Bavachinin in Non-Small-Cell Lung Cancer Cells. Molecules (Basel, Switzerland). 2021 Aug; 26(17):. doi: 10.3390/molecules26175161. [PMID: 34500594]
  • Chunxia Zhang, Qian Qin, Hongle Li. Targeted Therapeutic Effect of Bavachinin Nanospheres on Pathological Site of Chronic Asthmatic Mice Model. Journal of nanoscience and nanotechnology. 2021 02; 21(2):1085-1090. doi: 10.1166/jnn.2021.18641. [PMID: 33183447]
  • Xi Dong, Yue Zhu, Shan Wang, Yun Luo, Shan Lu, Fengwei Nan, Guibo Sun, Xiaobo Sun. Bavachinin inhibits cholesterol synthesis enzyme FDFT1 expression via AKT/mTOR/SREBP-2 pathway. International immunopharmacology. 2020 Nov; 88(?):106865. doi: 10.1016/j.intimp.2020.106865. [PMID: 32827918]
  • Zhi-Xing Zhou, Li Yang, Li-Yuan Cheng, Ying-Li Yu, Lei Song, Kun Zhou, Ying-Liang Wu, Yue Zhang. Simultaneous characterization of multiple Psoraleae Fructus bioactive compounds in rat plasma by ultra-high-performance liquid chromatography coupled with triple quadrupole mass spectrometry for application in sex-related differences in pharmacokinetics. Journal of separation science. 2020 Jul; 43(14):2804-2816. doi: 10.1002/jssc.202000286. [PMID: 32384213]
  • Jun Qian, Fan Xie, Yanhong Shi, Jinhang Li, Liuqiang Zhang, Yiming Li, Fujiang Guo, Rui Wang. Pharmacokinetic and metabolism studies of bavachinin through ultra-high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Biomedical chromatography : BMC. 2018 Oct; 32(10):e4293. doi: 10.1002/bmc.4293. [PMID: 29782651]
  • Shan Wang, Min Wang, Min Wang, Yu Tian, Xiao Sun, Guibo Sun, Xiaobo Sun. Bavachinin Induces Oxidative Damage in HepaRG Cells through p38/JNK MAPK Pathways. Toxins. 2018 04; 10(4):. doi: 10.3390/toxins10040154. [PMID: 29649125]
  • Nidhi Gupta, Arem Qayum, Arun Raina, Ravi Shankar, Sumeet Gairola, Shashank Singh, Payare L Sangwan. Synthesis and biological evaluation of novel bavachinin analogs as anticancer agents. European journal of medicinal chemistry. 2018 Feb; 145(?):511-523. doi: 10.1016/j.ejmech.2018.01.006. [PMID: 29335212]
  • Guoxin Du, Yuanyuan Zhao, Li Feng, Zhuo Yang, Jiye Shi, Cheng Huang, Bo Li, Fujiang Guo, Weiliang Zhu, Yiming Li. Design, Synthesis, and Structure-Activity Relationships of Bavachinin Analogues as Peroxisome Proliferator-Activated Receptor γ Agonists. ChemMedChem. 2017 01; 12(2):183-193. doi: 10.1002/cmdc.201600554. [PMID: 27914122]
  • Li Feng, Huan Luo, Zhijian Xu, Zhuo Yang, Guoxin Du, Yu Zhang, Lijing Yu, Kaifeng Hu, Weiliang Zhu, Qingchun Tong, Kaixian Chen, Fujiang Guo, Cheng Huang, Yiming Li. Bavachinin, as a novel natural pan-PPAR agonist, exhibits unique synergistic effects with synthetic PPAR-γ and PPAR-α agonists on carbohydrate and lipid metabolism in db/db and diet-induced obese mice. Diabetologia. 2016 06; 59(6):1276-86. doi: 10.1007/s00125-016-3912-9. [PMID: 26983922]
  • Li-Wei Zou, Yao-Guang Li, Ping Wang, Kun Zhou, Jie Hou, Qiang Jin, Da-Cheng Hao, Guang-Bo Ge, Ling Yang. Design, synthesis, and structure-activity relationship study of glycyrrhetinic acid derivatives as potent and selective inhibitors against human carboxylesterase 2. European journal of medicinal chemistry. 2016 Apr; 112(?):280-288. doi: 10.1016/j.ejmech.2016.02.020. [PMID: 26900660]
  • Dong-Xue Sun, Guang-Bo Ge, Pei-Pei Dong, Yun-Feng Cao, Zhi-Wei Fu, Rui-Xue Ran, Xue Wu, Yan-Yan Zhang, Hui-Ming Hua, Zhenying Zhao, Zhong-Ze Fang. Inhibition behavior of fructus psoraleae's ingredients towards human carboxylesterase 1 (hCES1). Xenobiotica; the fate of foreign compounds in biological systems. 2016; 46(6):503-10. doi: 10.3109/00498254.2015.1091521. [PMID: 26560012]
  • Fan Xie, Guoxin Du, Shunan Ma, Yiming Li, Rui Wang, Fujiang Guo. Structural elucidation of in vitro metabolites of bavachinin in rat liver microsomes by LC-ESI-MSn and chemical synthesis. Xenobiotica; the fate of foreign compounds in biological systems. 2016; 46(4):296-306. doi: 10.3109/00498254.2015.1074763. [PMID: 26259024]
  • Xin-Xin Wang, Xia Lv, Shi-Yang Li, Jie Hou, Jing Ning, Jia-Yue Wang, Yun-Feng Cao, Guang-Bo Ge, Bin Guo, Ling Yang. Identification and characterization of naturally occurring inhibitors against UDP-glucuronosyltransferase 1A1 in Fructus Psoraleae (Bu-gu-zhi). Toxicology and applied pharmacology. 2015 Nov; 289(1):70-8. doi: 10.1016/j.taap.2015.09.003. [PMID: 26348140]
  • Guoxin Du, Li Feng, Zhuo Yang, Jiye Shi, Cheng Huang, Fujiang Guo, Bo Li, Weiliang Zhu, Yiming Li. Separation and peroxisome proliferator-activated receptor-γ agonist activity evaluation of synthetic racemic bavachinin enantiomers. Bioorganic & medicinal chemistry letters. 2015 Jun; 25(12):2579-83. doi: 10.1016/j.bmcl.2015.04.029. [PMID: 25978962]
  • Haiyan Zhao, Zilin Chen. Screening of neuraminidase inhibitors from traditional Chinese medicines by integrating capillary electrophoresis with immobilized enzyme microreactor. Journal of chromatography. A. 2014 May; 1340(?):139-45. doi: 10.1016/j.chroma.2014.03.028. [PMID: 24679826]
  • Jianmei Luo, Qikun Liang, Yanbing Shen, Xi Chen, Zhinan Yin, Min Wang. Biotransformation of bavachinin by three fungal cell cultures. Journal of bioscience and bioengineering. 2014 Feb; 117(2):191-196. doi: 10.1016/j.jbiosc.2013.08.001. [PMID: 24012108]
  • Xiumin Chen, Yanfang Yang, Yingtao Zhang. Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro. FEBS letters. 2013 Sep; 587(18):2930-5. doi: 10.1016/j.febslet.2013.07.037. [PMID: 23907009]
  • Seung Woong Lee, Bo Ra Yun, Mi Hwa Kim, Chan Sun Park, Woo Song Lee, Hyun-Mee Oh, Mun-Chual Rho. Phenolic compounds isolated from Psoralea corylifolia inhibit IL-6-induced STAT3 activation. Planta medica. 2012 Jun; 78(9):903-6. doi: 10.1055/s-0031-1298482. [PMID: 22573369]
  • Lei Liu, Kang-Ning Liu, Ya-Bin Wen, Han-Wen Zhang, Ya-Xin Lu, Zheng Yin. Development of a fully automated on-line solid phase extraction and high-performance liquid chromatography with diode array detection method for the pharmacokinetic evaluation of bavachinin: a study on absolute bioavailability and dose proportionality. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Apr; 893-894(?):21-8. doi: 10.1016/j.jchromb.2012.02.020. [PMID: 22444438]
  • Ming Hong Lee, Jae Yeon Kim, Jae-Ha Ryu. Prenylflavones from Psoralea corylifolia inhibit nitric oxide synthase expression through the inhibition of I-kappaB-alpha degradation in activated microglial cells. Biological & pharmaceutical bulletin. 2005 Dec; 28(12):2253-7. doi: 10.1248/bpb.28.2253. [PMID: 16327160]
  • Hiroyuki Haraguchi, Junji Inoue, Yukiyoshi Tamura, Kenji Mizutani. Antioxidative components of Psoralea corylifolia (Leguminosae). Phytotherapy research : PTR. 2002 Sep; 16(6):539-44. doi: 10.1002/ptr.972. [PMID: 12237811]