Bufogenin (BioDeep_00000176866)

   

human metabolite blood metabolite natural product


代谢物信息卡片


5-{14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl}-2H-pyran-2-one

化学式: C24H32O4 (384.23)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 100%

分子结构信息

SMILES: CC12CCC(CC1CCC3C2CCC4(C35C(O5)CC4C6=COC(=O)C=C6)C)O
InChI: InChI=1S/C24H32O4/c1-22-9-7-16(25)11-15(22)4-5-18-17(22)8-10-23(2)19(12-20-24(18,23)28-20)14-3-6-21(26)27-13-14/h3,6,13,15-20,25H,4-5,7-12H2,1-2H3

描述信息

D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002018 - Bufanolides
D002317 - Cardiovascular Agents

同义名列表

3 个代谢物同义名

5-{14-hydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-6-yl}-2H-pyran-2-one; Resibufogenin; bufogenin



数据库引用编号

6 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)

37 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。

亚细胞结构定位 关联基因列表
Cytoplasm 14 HRAS, LPO, MAP2K1, MAP3K5, MAP3K8, MAPK11, MAPK14, MAPK3, MAPK7, MAPK9, MARVELD2, RIGI, SULT2A1, TLR7
Peripheral membrane protein 1 MAP2K1
Endosome membrane 2 TLR7, TLR8
Endoplasmic reticulum membrane 4 HRAS, TLR7, TLR8, WLS
Nucleus 8 HPSE, IRF4, MAP2K1, MAPK11, MAPK14, MAPK3, MAPK7, MAPK9
cytosol 13 HRAS, IRF4, MAP2K1, MAP3K5, MAP3K8, MAPK11, MAPK14, MAPK3, MAPK7, MAPK9, RIGI, SULT2A1, WLS
trans-Golgi network 1 WLS
centrosome 1 MAP2K1
nucleoplasm 9 ATP2B1, HPSE, HRAS, IRF4, MAPK11, MAPK14, MAPK3, MAPK7, MAPK9
Cell membrane 4 ATP2B1, HRAS, MARVELD2, WLS
Lipid-anchor 1 HRAS
Cytoplasmic side 1 HRAS
ruffle membrane 1 RIGI
Early endosome membrane 1 WLS
Multi-pass membrane protein 3 ATP2B1, MARVELD2, WLS
Golgi apparatus membrane 2 HRAS, WLS
Synapse 1 ATP2B1
cell junction 1 MARVELD2
glutamatergic synapse 4 ATP2B1, HRAS, MAPK14, MAPK3
Golgi apparatus 4 HRAS, MAP2K1, MAPK3, WLS
Golgi membrane 5 HRAS, INS, TLR7, TLR8, WLS
lysosomal membrane 1 HPSE
presynaptic membrane 1 ATP2B1
Lysosome 2 HPSE, TLR7
endosome 2 TLR7, TLR8
plasma membrane 9 ATP2B1, HRAS, MAP2K1, MAPK3, MAPK9, MARVELD2, TLR7, TLR8, WLS
synaptic vesicle membrane 1 ATP2B1
Membrane 9 ATP2B1, HPSE, HRAS, IRF4, MAP2K1, MARVELD2, TLR7, TLR8, WLS
apical plasma membrane 1 MARVELD2
basolateral plasma membrane 3 ATP2B1, LPO, MARVELD2
caveola 1 MAPK3
extracellular exosome 3 ATP2B1, LPO, WLS
endoplasmic reticulum 3 MAP2K1, TLR7, WLS
extracellular space 3 HPSE, INS, LPO
lysosomal lumen 1 HPSE
perinuclear region of cytoplasm 1 HRAS
Schaffer collateral - CA1 synapse 1 MAPK9
Cell junction, tight junction 1 MARVELD2
bicellular tight junction 2 MARVELD2, RIGI
mitochondrion 4 MAP2K1, MAPK14, MAPK3, MAPK9
protein-containing complex 1 MAP3K5
intracellular membrane-bounded organelle 2 ATP2B1, HPSE
Single-pass type I membrane protein 2 TLR7, TLR8
Secreted 3 HPSE, INS, LPO
extracellular region 4 HPSE, INS, LPO, MAPK14
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 MAP2K1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 2 MAP3K5, TLR8
actin cytoskeleton 1 RIGI
cytoplasmic vesicle 2 MARVELD2, WLS
Early endosome 3 MAP2K1, MAPK3, WLS
Membrane raft 1 HPSE
Cell junction, focal adhesion 1 MAPK3
focal adhesion 2 MAP2K1, MAPK3
extracellular matrix 1 HPSE
PML body 1 MAPK7
lateral plasma membrane 1 ATP2B1
nuclear speck 2 MAPK14, MAPK9
Late endosome 2 MAP2K1, MAPK3
receptor complex 1 TLR7
chromatin 1 IRF4
cell projection 1 ATP2B1
cytoskeleton 1 MAPK3
spindle pole 1 MAPK14
Cytoplasm, cytoskeleton, microtubule organizing center, spindle pole body 1 MAP2K1
spindle pole body 1 MAP2K1
Basolateral cell membrane 1 ATP2B1
organelle membrane 1 WLS
nuclear envelope 1 MAPK3
Endomembrane system 4 HRAS, TLR7, TLR8, WLS
endosome lumen 1 INS
Membrane, caveola 1 MAPK3
Cytoplasmic vesicle membrane 1 WLS
Presynaptic cell membrane 1 ATP2B1
pseudopodium 1 MAPK3
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 INS, MAPK14
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, MAPK3
specific granule lumen 1 HPSE
endocytic vesicle membrane 1 WLS
transport vesicle 1 INS
Schmidt-Lanterman incisure 1 MARVELD2
tight junction 1 MARVELD2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 ATP2B1
ribonucleoprotein complex 1 RIGI
paranodal junction 1 MARVELD2
endolysosome membrane 2 TLR7, TLR8
nucleosome 1 IRF4
early phagosome 1 TLR7
tricellular tight junction 1 MARVELD2
Cytoplasmic vesicle, phagosome 1 TLR7
IRE1-TRAF2-ASK1 complex 1 MAP3K5
GTPase complex 1 HRAS
protein kinase complex 1 MAP3K5
photoreceptor ribbon synapse 1 ATP2B1


文献列表

  • Hao Zhang, Baiyu Jian. Resibufogenin: An Emerging Therapeutic Compound with Multifaceted Pharmacological Effects - A Comprehensive Review. Medical science monitor : international medical journal of experimental and clinical research. 2024 Feb; 30(?):e942783. doi: 10.12659/msm.942783. [PMID: 38369741]
  • Kento Takaya, Toru Asou, Kazuo Kishi. Identification of resibufogenin, a component of toad venom, as a novel senolytic compound in vitro and for potential skin rejuvenation in male mice. Biogerontology. 2023 12; 24(6):889-900. doi: 10.1007/s10522-023-10043-0. [PMID: 37395866]
  • Yuan Gao, Zhenlu Xu, Ximeng Li, Zhuangzhuang Liu, Wenjing Li, Yuan Kang, Xiaoyu Zhang, Yun Qi. Resibufogenin, one of bufadienolides in toad venom, suppresses LPS-induced inflammation via inhibiting NF-κB and AP-1 pathways. International immunopharmacology. 2022 Dec; 113(Pt A):109312. doi: 10.1016/j.intimp.2022.109312. [PMID: 36252491]
  • Tao Song, Jiajia Li, Mingye Wang, Min Su, Dengfeng Xu, Luheng Zhou, Xiaopei Zhang, Hongtao Wang, Yunlong Hou. Analysis of Resibufogenin on Cardiac conduction reveals a species difference in the cardiac electrophysiology: Rats versus guinea pigs. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 Jul; 139(?):111581. doi: 10.1016/j.biopha.2021.111581. [PMID: 33895523]
  • Qian Li, Chuanwu Jiang, Yan Wang, Minghua Wei, Huijin Zheng, Yanqi Xu, Xuegang Xu, Fengyu Jia, Kai Liu, Gang Sun, Jianhua Zang, Ping Mo. Resibufogenin suppresses tumor growth and inhibits glycolysis in ovarian cancer by modulating PIM1. Naunyn-Schmiedeberg's archives of pharmacology. 2019 12; 392(12):1477-1489. doi: 10.1007/s00210-019-01687-2. [PMID: 31292669]
  • Yueting Cao, Jiheng Wu, Hongye Pan, Longhu Wang. Chemical Profile and Multicomponent Quantitative Analysis for the Quality Evaluation of Toad Venom from Different Origins. Molecules (Basel, Switzerland). 2019 Oct; 24(19):. doi: 10.3390/molecules24193595. [PMID: 31590467]
  • Wen-Long Wei, Ya-Ling An, Zhen-Wei Li, Ying-Ying Wang, Hong-Jian Ji, Jin-Jun Hou, Wan-Ying Wu, De-An Guo. Simultaneous determination of resibufogenin and its eight metabolites in rat plasma by LC-MS/MS for metabolic profiles and pharmacokinetic study. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Jul; 60(?):152971. doi: 10.1016/j.phymed.2019.152971. [PMID: 31178234]
  • Yue-Ting Cao, Ke-Ke Cui, Ji-Heng Wu, Hong-Ye Pan, Zheng-Yu Lu, Jia-Feng Shao, Long-Hu Wang. [Correlative study of bufogenin constituents in venom of Bufo bufo gargarizans]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2019 May; 44(9):1850-1856. doi: 10.19540/j.cnki.cjcmm.20190222.003. [PMID: 31342712]
  • Lu Liu, Yang Liu, Xiaojia Liu, Na Zhang, Genxiang Mao, Qingxuan Zeng, Mingxiao Yin, Danqing Song, Hongbin Deng. Resibufogenin suppresses transforming growth factor-β-activated kinase 1-mediated nuclear factor-κB activity through protein kinase C-dependent inhibition of glycogen synthase kinase 3. Cancer science. 2018 Nov; 109(11):3611-3622. doi: 10.1111/cas.13788. [PMID: 30168902]
  • Qinrui Han, Ye Ma, Hao Wang, Yu Dai, Chunhui Chen, Yawei Liu, Linlin Jing, Xuegang Sun. Resibufogenin suppresses colorectal cancer growth and metastasis through RIP3-mediated necroptosis. Journal of translational medicine. 2018 07; 16(1):201. doi: 10.1186/s12967-018-1580-x. [PMID: 30029665]
  • Hao Dong, Li Tian, Meng Gao, Hong Xu, Chenghong Zhang, Li Lv, Jianbin Zhang, Changyuan Wang, Yan Tian, Xiaochi Ma. Promising galactose-decorated biodegradable poloxamer 188-PLGA diblock copolymer nanoparticles of resibufogenin for enhancing liver cancer therapy. Drug delivery. 2017 Nov; 24(1):1302-1316. doi: 10.1080/10717544.2017.1373165. [PMID: 28895767]
  • Qiuchen Chu, Hong Xu, Meng Gao, Xin Guan, Hongyan Liu, Sa Deng, Xiaokui Huo, Kexin Liu, Yan Tian, Xiaochi Ma. Liver-targeting Resibufogenin-loaded poly(lactic-co-glycolic acid)-D-α-tocopheryl polyethylene glycol 1000 succinate nanoparticles for liver cancer therapy. International journal of nanomedicine. 2016; 11(?):449-63. doi: 10.2147/ijn.s93541. [PMID: 26869788]
  • Jing Ning, Zhen-Long Yu, Liang-Hai Hu, Chao Wang, Xiao-Kui Huo, Sa Deng, Jie Hou, Jing-Jing Wu, Guang-Bo Ge, Xiao-Chi Ma, Ling Yang. Characterization of phase I metabolism of resibufogenin and evaluation of the metabolic effects on its antitumor activity and toxicity. Drug metabolism and disposition: the biological fate of chemicals. 2015 Mar; 43(3):299-308. doi: 10.1124/dmd.114.060996. [PMID: 25504504]
  • Masami Ichikawa, Yoshihiro Sowa, Yosuke Iizumi, Yuichi Aono, Toshiyuki Sakai. Resibufogenin Induces G1-Phase Arrest through the Proteasomal Degradation of Cyclin D1 in Human Malignant Tumor Cells. PloS one. 2015; 10(6):e0129851. doi: 10.1371/journal.pone.0129851. [PMID: 26121043]
  • Jules B Puschett. Marinobufagenin predicts and resibufogenin prevents preeclampsia: a review of the evidence. American journal of perinatology. 2012 Nov; 29(10):777-85. doi: 10.1055/s-0032-1316447. [PMID: 22814872]
  • Rui-Fang Xie, Zhi-Cheng Li, Bo Gao, Zhi-Na Shi, Xin Zhou. Bufothionine, a possible effective component in cinobufocini injection for hepatocellular carcinoma. Journal of ethnopharmacology. 2012 Jun; 141(2):692-700. doi: 10.1016/j.jep.2011.12.018. [PMID: 22210051]
  • Bo Jiang, Fei Cai, Shouhong Gao, Liyuan Meng, Fengying Liang, Xiao Dai, Wen Xu, Wansheng Chen. Induction of cytochrome P450 3A by Shexiang Baoxin Pill and its main components. Chemico-biological interactions. 2012 Jan; 195(2):105-13. doi: 10.1016/j.cbi.2011.12.001. [PMID: 22178124]
  • Zongyun Li, Huimin Gao, Jinhua Wang, Ting Qu, Liangmian Chen, Zhimin Wang, Qiwei Zhang. [Inhibitory effect of total bufadienolides from toad venom against H22 tumor in mice and their metabolites]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Nov; 36(21):2987-93. doi: . [PMID: 22308689]
  • Shuang Hao, Yong-Ming Bao, Rong-Guo Zhao, He-Shuang Wang, Jing Bi, Li-Jia An, Bo Jiang. Effects of resibufogenin on voltage-gated sodium channels in cultured rat hippocampal neurons. Neuroscience letters. 2011 Aug; 501(2):112-6. doi: 10.1016/j.neulet.2011.06.059. [PMID: 21763753]
  • Fanghua Qi, Anyuan Li, Yoshinori Inagaki, Norihiro Kokudo, Sumihito Tamura, Munehiro Nakata, Wei Tang. Antitumor activity of extracts and compounds from the skin of the toad Bufo bufo gargarizans Cantor. International immunopharmacology. 2011 Mar; 11(3):342-9. doi: 10.1016/j.intimp.2010.12.007. [PMID: 21185919]
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  • Jules B Puschett, Enoch Agunanne, Mohammad N Uddin. Emerging role of the bufadienolides in cardiovascular and kidney diseases. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2010 Aug; 56(2):359-70. doi: 10.1053/j.ajkd.2010.01.023. [PMID: 20417001]
  • Xiu Lan Xin, Junying Liu, Xiao Chi Ma, Qing Wei, Li Lv, Chang Yuan Wang, Ji Hong Yao, Jian Cui. Preparative separation of four major bufadienolides from the Chinese traditional medicine, Chansu, using high-speed counter-current chromatography. Natural product communications. 2010 Jul; 5(7):1031-4. doi: . [PMID: 20734934]
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  • Fang Li, Rui Yang, Yan Weng, Xing Tang. Preparation and evaluation of lyophilized liposome-encapsulated bufadienolides. Drug development and industrial pharmacy. 2009 Sep; 35(9):1048-58. doi: 10.1080/03639040902762987. [PMID: 19365782]
  • Chris Kostakis, Roger W Byard. Sudden death associated with intravenous injection of toad extract. Forensic science international. 2009 Jul; 188(1-3):e1-5. doi: 10.1016/j.forsciint.2009.02.006. [PMID: 19303230]
  • Xiao Chi Ma, Bao Jing Zhang, Xin Lan Xin, Shan Shan Huang, Sha Deng, Hou Li Zhang, Xiao Hong Shu, Yun Peng Diao, Jian Cui. Simultaneous quantification of seven major bufadienolides in three traditional Chinese medicinal preparations of chansu by HPLC-DAD. Natural product communications. 2009 Feb; 4(2):179-84. doi: . [PMID: 19370919]
  • Yu Zhang, Xing Tang, Xiaoliang Liu, Fang Li, Xia Lin. Simultaneous determination of three bufadienolides in rat plasma after intravenous administration of bufadienolides extract by ultra performance liquid chromatography electrospray ionization tandem mass spectrometry. Analytica chimica acta. 2008 Mar; 610(2):224-31. doi: 10.1016/j.aca.2008.01.029. [PMID: 18291133]
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