Eupatolide (BioDeep_00000007376)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Eupatolide

化学式: C15H20O3 (248.1412)
中文名称: 泽兰内酯
谱图信息: 最多检出来源 Homo sapiens(COVID-19)(otcml) 26.64%

分子结构信息

SMILES: C=C1C(=O)OC2C=C(C)CCC=C(C)CC(O)C12
InChI: InChI=1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13-,14-/m1/s1

描述信息

A germacranolide with formula C15H20O3, isolated from several Inula species. It exhibits anti-cancer properties.

同义名列表

2 个代谢物同义名

Eupatolide; Eupatolide



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)

56 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 13 ANXA5, CASP8, CDH1, CFLAR, MAPK14, MAPK8, NFKB1, PIK3CA, PTGS2, SMAD3, SRARP, STAT3, VIM
Peripheral membrane protein 4 ANXA5, CYP1B1, GORASP1, PTGS2
Endoplasmic reticulum membrane 3 CYP1B1, HMOX1, PTGS2
Nucleus 12 CASP8, CDH1, GABPA, HMOX1, JUND, MAPK14, MAPK8, NFKB1, SMAD3, SRARP, STAT3, TGFBR1
cytosol 12 ANXA5, CASP8, CDH1, CFLAR, HMOX1, MAPK14, MAPK8, NFKB1, PIK3CA, SMAD3, STAT3, VIM
phagocytic vesicle 1 VIM
trans-Golgi network 1 CDH1
nucleoplasm 10 CASP8, CDH1, GABPA, HMOX1, JUND, MAPK14, MAPK8, NFKB1, SMAD3, STAT3
RNA polymerase II transcription regulator complex 2 JUND, STAT3
Cell membrane 4 CDH1, TGFBR1, TNF, VIM
Cytoplasmic side 2 GORASP1, HMOX1
lamellipodium 3 CASP8, CDH1, PIK3CA
Golgi apparatus membrane 1 GORASP1
Synapse 1 MAPK8
cell junction 1 CDH1
cell surface 2 TGFBR1, TNF
glutamatergic synapse 2 CDH1, MAPK14
Golgi apparatus 2 CDH1, GORASP1
Golgi membrane 1 GORASP1
neuronal cell body 1 TNF
postsynapse 1 CDH1
sarcolemma 1 ANXA5
endosome 2 CDH1, TGFBR1
plasma membrane 7 CDH1, PIK3CA, SMAD3, STAT3, TGFBR1, TNF, VIM
Membrane 5 ANXA5, CDH1, CYP1B1, HMOX1, TGFBR1
axon 2 MAPK8, VIM
caveola 1 PTGS2
extracellular exosome 3 ANXA5, CDH1, VIM
endoplasmic reticulum 2 HMOX1, PTGS2
extracellular space 2 HMOX1, TNF
perinuclear region of cytoplasm 3 CDH1, HMOX1, PIK3CA
Cell junction, tight junction 1 TGFBR1
adherens junction 1 CDH1
bicellular tight junction 1 TGFBR1
intercalated disc 1 PIK3CA
mitochondrion 4 CASP8, CYP1B1, MAPK14, NFKB1
protein-containing complex 2 CASP8, PTGS2
intracellular membrane-bounded organelle 1 CYP1B1
Microsome membrane 2 CYP1B1, PTGS2
Single-pass type I membrane protein 2 CDH1, TGFBR1
extracellular region 5 ANXA5, CDH1, MAPK14, NFKB1, TNF
cytoplasmic side of plasma membrane 1 CDH1
mitochondrial outer membrane 2 CASP8, HMOX1
transcription regulator complex 4 JUND, NFKB1, SMAD3, STAT3
nuclear membrane 1 CDH1
external side of plasma membrane 2 ANXA5, TNF
actin cytoskeleton 1 CDH1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cell projection, lamellipodium 1 CASP8
Membrane raft 2 TGFBR1, TNF
Cytoplasm, cytoskeleton 1 VIM
focal adhesion 2 ANXA5, VIM
cis-Golgi network 1 GORASP1
Cell junction, adherens junction 1 CDH1
flotillin complex 1 CDH1
Peroxisome 1 VIM
collagen-containing extracellular matrix 1 ANXA5
intermediate filament 1 VIM
lateral plasma membrane 1 CDH1
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 2 PTGS2, SMAD3
nuclear outer membrane 1 PTGS2
receptor complex 2 SMAD3, TGFBR1
Zymogen granule membrane 1 ANXA5
neuron projection 2 PTGS2, VIM
chromatin 5 GABPA, JUND, NFKB1, SMAD3, STAT3
cell leading edge 1 VIM
phagocytic cup 1 TNF
cytoskeleton 2 CASP8, VIM
Golgi apparatus, trans-Golgi network 1 CDH1
spindle pole 1 MAPK14
microtubule organizing center 1 VIM
cell body 1 CASP8
intermediate filament cytoskeleton 1 VIM
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 MAPK14, NFKB1
endoplasmic reticulum lumen 1 PTGS2
nuclear matrix 1 VIM
transcription repressor complex 1 JUND
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
specific granule lumen 1 NFKB1
anaphase-promoting complex 1 CDH1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
Nucleus matrix 1 VIM
vesicle membrane 1 ANXA5
[Isoform 2]: Nucleus 1 CDH1
heteromeric SMAD protein complex 1 SMAD3
SMAD protein complex 1 SMAD3
basal dendrite 1 MAPK8
CD95 death-inducing signaling complex 2 CASP8, CFLAR
death-inducing signaling complex 2 CASP8, CFLAR
ripoptosome 2 CASP8, CFLAR
apical junction complex 1 CDH1
Cell junction, desmosome 1 CDH1
desmosome 1 CDH1
catenin complex 1 CDH1
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
endothelial microparticle 1 ANXA5
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
activin receptor complex 1 TGFBR1
transforming growth factor beta ligand-receptor complex 1 TGFBR1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • InWha Park, Hee Sun Byun, Gang Min Hur, MinKyun Na. Tulipiferamide A, an Alkamide from Liriodendron tulipifera, Exhibits an Anti-Inflammatory Effect via Targeting IKKβ Phosphorylation. Journal of natural products. 2021 05; 84(5):1598-1606. doi: 10.1021/acs.jnatprod.1c00146. [PMID: 33939429]
  • Maximilian Frey, Katharina Schmauder, Irini Pateraki, Otmar Spring. Biosynthesis of Eupatolide-A Metabolic Route for Sesquiterpene Lactone Formation Involving the P450 Enzyme CYP71DD6. ACS chemical biology. 2018 06; 13(6):1536-1543. doi: 10.1021/acschembio.8b00126. [PMID: 29758164]
  • Xing-De Wu, Lin-Fen Ding, Wen-Chao Tu, Hui Yang, Jia Su, Li-Yan Peng, Yan Li, Qin-Shi Zhao. Bioactive sesquiterpenoids from the flowers of Inula japonica. Phytochemistry. 2016 Sep; 129(?):68-76. doi: 10.1016/j.phytochem.2016.07.008. [PMID: 27452450]
  • Namho Kim, Cheol Hwangbo, Suhyun Lee, Jeong-Hyung Lee. Eupatolide inhibits PDGF-induced proliferation and migration of aortic smooth muscle cells through ROS-dependent heme oxygenase-1 induction. Phytotherapy research : PTR. 2013 Nov; 27(11):1700-7. doi: 10.1002/ptr.4924. [PMID: 23297002]
  • Jongkyu Lee, Nara Tae, Jung Joon Lee, Taeho Kim, Jeong-Hyung Lee. Eupatolide inhibits lipopolysaccharide-induced COX-2 and iNOS expression in RAW264.7 cells by inducing proteasomal degradation of TRAF6. European journal of pharmacology. 2010 Jun; 636(1-3):173-80. doi: 10.1016/j.ejphar.2010.03.021. [PMID: 20353767]
  • Jongkyu Lee, Cheol Hwangbo, Jung Joon Lee, Juhee Seo, Jeong-Hyung Lee. The sesquiterpene lactone eupatolide sensitizes breast cancer cells to TRAIL through down-regulation of c-FLIP expression. Oncology reports. 2010 Jan; 23(1):229-37. doi: . [PMID: 19956887]
  • H J Hilderson, M J De Wolf, A R Lagrou, W S Dierick. Subcellular structure of bovine thyroid gland. A study on bovine thyroid membranes by buoyant-density-gradient centrifugation in a B-XIV zonal rotor. The Biochemical journal. 1975 Dec; 152(3):601-7. doi: 10.1042/bj1520601. [PMID: 5997]
  • K H Lee, H C Huang, E S Huang, H Furukawa. Antitumor agents. II. Eupatolide, a new cytotoxic principle from Eupatorium formosanum HAY. Journal of pharmaceutical sciences. 1972 Apr; 61(4):629-31. doi: 10.1002/jps.2600610432. [PMID: 4335375]