Mecheliolide (BioDeep_00000000297)

   

PANOMIX_OTCML-2023


代谢物信息卡片


[3aS-(3aalpha,9alpha,9aalpha,9bbeta)]-3a,4,5,7,8,9,9a,9b-Octahydro-9-hydroxy-6,9-dimethyl-3-methylene-azuleno[4,5-b]furan-2(3H)-one

化学式: C15H20O3 (248.1412)
中文名称: 乌心石内酯, 木香内酯
谱图信息: 最多检出来源 Macaca mulatta(otcml) 75%

分子结构信息

SMILES: C=C1C(=O)OC2C1CCC(C)=C1CCC(C)(O)C12
InChI: InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1



数据库引用编号

15 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)

4 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 15 ATG7, BECN1, CASP1, CASP3, CD34, IL18, MAPK14, MAPK3, MTDH, NFE2L2, NLRP3, PIK3CA, PTGS2, RELA, STAT3
Golgi apparatus, trans-Golgi network membrane 1 BECN1
Peripheral membrane protein 2 BECN1, PTGS2
Endosome membrane 1 BECN1
Endoplasmic reticulum membrane 4 BECN1, HMOX1, MTDH, PTGS2
Mitochondrion membrane 1 BECN1
Cytoplasmic vesicle, autophagosome 1 BECN1
Nucleus 10 BECN1, CASP3, HMOX1, MAPK14, MAPK3, MTDH, NFE2L2, NLRP3, RELA, STAT3
autophagosome 1 BECN1
cytosol 13 ATG7, BECN1, CASP1, CASP3, HMOX1, IL18, MAPK14, MAPK3, NFE2L2, NLRP3, PIK3CA, RELA, STAT3
dendrite 1 BECN1
mitochondrial membrane 1 BECN1
nuclear body 2 BECN1, MTDH
phagocytic vesicle 1 BECN1
phosphatidylinositol 3-kinase complex, class III 1 BECN1
trans-Golgi network 1 BECN1
centrosome 1 NFE2L2
nucleoplasm 7 CASP3, HMOX1, MAPK14, MAPK3, NFE2L2, RELA, STAT3
RNA polymerase II transcription regulator complex 2 NFE2L2, STAT3
Cell membrane 2 CASP1, TNF
Cytoplasmic side 1 HMOX1
lamellipodium 1 PIK3CA
Golgi apparatus membrane 1 NLRP3
cell surface 1 TNF
glutamatergic synapse 4 CASP3, MAPK14, MAPK3, RELA
Golgi apparatus 2 MAPK3, NFE2L2
Golgi membrane 1 NLRP3
neuronal cell body 2 CASP3, TNF
Cytoplasm, cytosol 3 IL18, NFE2L2, NLRP3
Lysosome 1 CD34
endosome 1 BECN1
plasma membrane 7 CASP1, CD34, MAPK3, NFE2L2, PIK3CA, STAT3, TNF
Membrane 4 CD34, HMOX1, MTDH, NLRP3
apical plasma membrane 2 CD34, MTDH
caveola 2 MAPK3, PTGS2
endoplasmic reticulum 5 BECN1, HMOX1, MTDH, NLRP3, PTGS2
extracellular space 6 CCL2, HMOX1, IL18, IL4, IL6, TNF
perinuclear region of cytoplasm 4 CD34, HMOX1, MTDH, PIK3CA
Cell junction, tight junction 1 MTDH
bicellular tight junction 1 MTDH
intercalated disc 1 PIK3CA
intercellular canaliculus 1 MTDH
mitochondrion 3 MAPK14, MAPK3, NLRP3
protein-containing complex 2 CASP1, PTGS2
Microsome membrane 1 PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 CD34
Secreted 5 CCL2, IL18, IL4, IL6, NLRP3
extracellular region 9 ATG7, CCL2, CD34, IL18, IL4, IL6, MAPK14, NLRP3, TNF
Single-pass membrane protein 1 MTDH
mitochondrial outer membrane 1 HMOX1
transcription regulator complex 2 RELA, STAT3
Nucleus membrane 1 MTDH
nuclear membrane 1 MTDH
external side of plasma membrane 2 CD34, TNF
nucleolus 1 CASP1
Early endosome 1 MAPK3
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
Cell junction, focal adhesion 1 MAPK3
focal adhesion 1 MAPK3
microtubule 1 CASP1
axoneme 1 ATG7
nuclear speck 1 MAPK14
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 2 CASP1, NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 MAPK3
neuron projection 1 PTGS2
chromatin 3 NFE2L2, RELA, STAT3
mediator complex 1 NFE2L2
phagocytic cup 1 TNF
cytoskeleton 1 MAPK3
Nucleus, nucleolus 1 MTDH
spindle pole 1 MAPK14
intercellular bridge 1 CD34
fibrillar center 1 MTDH
nuclear envelope 1 MAPK3
Endomembrane system 1 NLRP3
Membrane, caveola 1 MAPK3
microtubule organizing center 1 NLRP3
phagophore assembly site 2 ATG7, BECN1
phosphatidylinositol 3-kinase complex, class III, type I 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type II 1 BECN1
pseudopodium 1 MAPK3
basal plasma membrane 1 CD34
ficolin-1-rich granule lumen 2 ATG7, MAPK14
secretory granule lumen 2 ATG7, MAPK14
endoplasmic reticulum lumen 3 IL6, MAPK3, PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
Single-pass type IV membrane protein 1 HMOX1
AIM2 inflammasome complex 1 CASP1
protein-DNA complex 1 NFE2L2
death-inducing signaling complex 1 CASP3
canonical inflammasome complex 1 CASP1
Preautophagosomal structure 1 ATG7
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
NF-kappaB p50/p65 complex 1 RELA
NF-kappaB complex 1 RELA
cytoplasmic side of mitochondrial outer membrane 1 BECN1
glomerular endothelium fenestra 1 CD34
IPAF inflammasome complex 1 CASP1
NLRP1 inflammasome complex 1 CASP1
protease inhibitor complex 1 CASP1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[Beclin-1-C 35 kDa]: Mitochondrion 1 BECN1
[Beclin-1-C 37 kDa]: Mitochondrion 1 BECN1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Xing Luo, Yuehong Wang, Xinxin Zhu, Yuwu Chen, Biyi Xu, Xiaoxuan Bai, Xiuzhu Weng, Jinmei Xu, Yangyang Tao, Dan Yang, Jie Du, Ying Lv, Shan Zhang, Sining Hu, Ji Li, Haibo Jia. MCL attenuates atherosclerosis by suppressing macrophage ferroptosis via targeting KEAP1/NRF2 interaction. Redox biology. 2024 Feb; 69(?):102987. doi: 10.1016/j.redox.2023.102987. [PMID: 38100883]
  • Yubo Dong, Xuanjin Qian, Jian Li. Sesquiterpene Lactones and Cancer: New Insight into Antitumor and Anti-inflammatory Effects of Parthenolide-Derived Dimethylaminomicheliolide and Micheliolide. Computational and mathematical methods in medicine. 2022; 2022(?):3744837. doi: 10.1155/2022/3744837. [PMID: 35898475]
  • Xianghong Lei, Shuting Li, Congwei Luo, Yuxian Wang, Yanxia Liu, Zhaozhong Xu, Qianyin Huang, Fangqin Zou, Yihua Chen, Fenfen Peng, Haibo Long. Micheliolide Attenuates Lipopolysaccharide-Induced Inflammation by Modulating the mROS/NF-κB/NLRP3 Axis in Renal Tubular Epithelial Cells. Mediators of inflammation. 2020; 2020(?):3934769. doi: 10.1155/2020/3934769. [PMID: 32879619]
  • Wenting Liu, Xiaowen Chen, Yuxian Wang, Yihua Chen, Sijia Chen, Wangqiu Gong, Ting Chen, Lingzhi Sun, Chenghao Zheng, Bohui Yin, Shuting Li, Congwei Luo, Qianyin Huang, Jing Xiao, Zhaozhong Xu, Fenfen Peng, Haibo Long. Micheliolide ameliorates diabetic kidney disease by inhibiting Mtdh-mediated renal inflammation in type 2 diabetic db/db mice. Pharmacological research. 2019 12; 150(?):104506. doi: 10.1016/j.phrs.2019.104506. [PMID: 31669149]
  • Wei-Feng Gao, Yi-Xuan Li, Wei-Hua Zhang, Ran Tao, Ting-Ting Yin, Yi-Jia Wang, Li-Na Liu, Zhi-Wei Fu, Sai-Nan Li, Nai-Rong Liu, Heng Zhang, Guang Liu, Li-Zhong Zhao, Xi-Peng Zhang, Chun-Ze Zhang. Comparison of the inhibition potential of parthenolide and micheliolide on various UDP-glucuronosyltransferase isoforms. Xenobiotica; the fate of foreign compounds in biological systems. 2019 Oct; 49(10):1158-1163. doi: 10.1080/00498254.2018.1544383. [PMID: 30484368]
  • Ashkan Kalantary-Charvadeh, Davoud Sanajou, Mohsen Hemmati-Dinarvand, Yasser Marandi, Mehran Khojastehfard, Hamed Hajipour, Mehran Mesgari-Abbasi, Leila Roshangar, Saeed Nazari Soltan Ahmad. Micheliolide Protects Against Doxorubicin-Induced Cardiotoxicity in Mice by Regulating PI3K/Akt/NF-kB Signaling Pathway. Cardiovascular toxicology. 2019 08; 19(4):297-305. doi: 10.1007/s12012-019-09511-2. [PMID: 30835049]
  • Fenfen Peng, Hongyu Li, Shuting Li, Yuxian Wang, Wenting Liu, Wangqiu Gong, Bohui Yin, Sijia Chen, Ying Zhang, Congwei Luo, Weidong Zhou, Yihua Chen, Peilin Li, Qianyin Huang, Zhaozhong Xu, Haibo Long. Micheliolide ameliorates renal fibrosis by suppressing the Mtdh/BMP/MAPK pathway. Laboratory investigation; a journal of technical methods and pathology. 2019 07; 99(8):1092-1106. doi: 10.1038/s41374-019-0245-6. [PMID: 30976056]
  • Xiaogang Tang, Qiulong Ding, Chao Chen, Fei Chen, Xiyang Zhou, Chu Jie Hong, Wensheng Pan. Micheliolide inhibits gastric cancer growth in vitro and in vivo via blockade of the IL-6/STAT3 pathway. Die Pharmazie. 2019 03; 74(3):175-178. doi: 10.1691/ph.2019.8816. [PMID: 30961685]
  • Jiabin Zhu, Jun Zhao, Zhenlong Yu, Sandeep Shrestha, Jing Song, Wenwen Liu, Wen Lan, Jinshan Xing, Shuang Liu, Chen Chen, Momo Cao, Xiuzhen Sun, Qi Wang, Xishuang Song. Epoxymicheliolide, a novelguaiane-type sesquiterpene lactone, inhibits NF‑κB/COX‑2 signaling pathways by targeting leucine 281 and leucine 25 in IKKβ in renal cell carcinoma. International journal of oncology. 2018 Sep; 53(3):987-1000. doi: 10.3892/ijo.2018.4460. [PMID: 29956738]
  • Juan Zhong, Wangqiu Gong, Jing Chen, Yao Qing, Shuyue Wu, Hongbei Li, Chunxi Huang, Yihua Chen, Yuxian Wang, Zhaozhong Xu, Wenting Liu, HongYu Li, Haibo Long. Micheliolide alleviates hepatic steatosis in db/db mice by inhibiting inflammation and promoting autophagy via PPAR-γ-mediated NF-кB and AMPK/mTOR signaling. International immunopharmacology. 2018 Jun; 59(?):197-208. doi: 10.1016/j.intimp.2018.03.036. [PMID: 29656210]
  • Xinru Jiang, Yuli Wang, Yifei Qin, Weigang He, Adel Benlahrech, Qingwen Zhang, Xin Jiang, Zhenhui Lu, Guang Ji, Yuejuan Zheng. Micheliolide provides protection of mice against Staphylococcus aureus and MRSA infection by down-regulating inflammatory response. Scientific reports. 2017 02; 7(?):41964. doi: 10.1038/srep41964. [PMID: 28165033]
  • Qingwen Zhang, Xinru Jiang, Weigang He, Kailin Wei, Jinxia Sun, Xiangyang Qin, Yuejuan Zheng, Xin Jiang. MCL Plays an Anti-Inflammatory Role in Mycobacterium tuberculosis-Induced Immune Response by Inhibiting NF-κB and NLRP3 Inflammasome Activation. Mediators of inflammation. 2017; 2017(?):2432904. doi: 10.1155/2017/2432904. [PMID: 28642632]
  • Xiangyang Qin, Xinru Jiang, Xin Jiang, Yuli Wang, Zhulei Miao, Weigang He, Guizhen Yang, Zhenhui Lv, Yizhi Yu, Yuejuan Zheng. Micheliolide inhibits LPS-induced inflammatory response and protects mice from LPS challenge. Scientific reports. 2016 Mar; 6(?):23240. doi: 10.1038/srep23240. [PMID: 26984741]
  • Hua Xu, Jian Wang, Chijuan Wang, Guoqiang Chang, Yani Lin, Hongju Zhang, Hairui Zhang, Qinghua Li, Tianxiang Pang. Therapeutic effects of micheliolide on a murine model of rheumatoid arthritis. Molecular medicine reports. 2015 Jan; 11(1):489-93. doi: 10.3892/mmr.2014.2767. [PMID: 25351212]
  • Katarzyna Gach, Anna Janecka. α-Methylene-γ-lactones as a novel class of anti-leukemic agents. Anti-cancer agents in medicinal chemistry. 2014 Jun; 14(5):688-94. doi: 10.2174/1871520614666140313095010. [PMID: 24628266]
  • Quan Zhang, Yaxin Lu, Yahui Ding, Jiadai Zhai, Qing Ji, Weiwei Ma, Ming Yang, Hongxia Fan, Jing Long, Zhongsheng Tong, Yehui Shi, Yongsheng Jia, Bin Han, Wenpeng Zhang, Chuanjiang Qiu, Xiaoyan Ma, Qiuying Li, Qianqian Shi, Haoliang Zhang, Dongmei Li, Jing Zhang, Jianping Lin, Lu-Yuan Li, Yingdai Gao, Yue Chen. Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells. Journal of medicinal chemistry. 2012 Oct; 55(20):8757-69. doi: 10.1021/jm301064b. [PMID: 22985027]
  • C L Cantrell, S G Franzblau, N H Fischer. Antimycobacterial plant terpenoids. Planta medica. 2001 Nov; 67(8):685-94. doi: 10.1055/s-2001-18365. [PMID: 11731906]
  • O O Barriga. Depression of cell-mediated immunity following inoculation of Trichinella spiralis extract in the mouse. Immunology. 1978 Jan; 34(1):167-73. doi: NULL. [PMID: 23994]
  • R J Roberts. Bacterial diseases of farmed fishes. Society for Applied Bacteriology symposium series. 1976; 4(?):55-62. doi: NULL. [PMID: 5781]