Eupatolide (BioDeep_00000007376)

PANOMIX_OTCML-2023 natural product Volatile Flavor Compounds

代谢物信息卡片

Eupatolide

化学式: C15H20O3 (248.14123700000002)
中文名称: 泽兰内酯
谱图信息: 最多检出来源 Macaca mulatta(otcml) 4.2%

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

ChEBI: CHEBI:4935
KEGG: C09440
PubChem: 5281460
PubChem: 98949
Metlin: METLIN67698
ChEMBL: CHEMBL485296
KNApSAcK: C00003277
CAS: 6750-25-0
PMhub: MS000020718
MetaboLights: MTBLC4935
PubChem: 11631
3DMET: B02968
NIKKAJI: J20.676H
LOTUS: LTS0263103
KNApSAcK: 4935

分类词条

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

1048900 - Aldama: LTS0263103
2770833 - Aldama linearis: 10.1016/S0031-9422(00)83114-3
2805006 - Aldama tukumanensis:
4210 - Asteraceae: LTS0263103
125672 - Cassinia: LTS0263103
1284849 - Cassinia aculeata: 10.1016/0031-9422(90)80185-J
1284849 - Cassinia aculeata: LTS0263103
1285786 - Cassinia arcuata: 10.1016/0031-9422(91)85114-F
1284881 - Cassinia subtropica: 10.1016/0031-9422(88)83027-9
1284881 - Cassinia subtropica: LTS0263103
1745051 - Disynaphia multicrenulata: 10.1016/S0305-1978(00)00092-2
2759 - Eukaryota: LTS0263103
13516 - Eupatorium: LTS0263103
102770 - Eupatorium cannabinum:
102770 - Eupatorium cannabinum: 10.1055/S-2006-962665
102772 - Eupatorium chinense:
102772 - Eupatorium chinense: 10.1021/JO01329A039
102772 - Eupatorium chinense: 10.1248/CPB.50.1250
102772 - Eupatorium chinense: LTS0263103
103749 - Eupatorium formosanum:
103749 - Eupatorium formosanum: 10.1016/S0040-4039(01)91862-3
103750 - Eupatorium glehni: 10.1248/CPB.50.1250
103750 - Eupatorium glehni: LTS0263103
176535 - Florestina tripteris: 10.1016/0031-9422(88)83154-6
4231 - Helianthus: LTS0263103
73275 - Helianthus argophyllus:
73275 - Helianthus argophyllus: 10.1016/0031-9422(82)83171-3
73275 - Helianthus argophyllus: LTS0263103
41589 - Inula: LTS0263103
453958 - Inula japonica:
453958 - Inula japonica: 10.1016/S0031-9422(00)90865-3
453958 - Inula japonica: LTS0263103
557660 - Inula salsoloides:
557660 - Inula salsoloides: 10.1002/HLCA.201000195
557660 - Inula salsoloides: 10.1016/0031-9422(95)00807-1
557660 - Inula salsoloides: 10.1016/S0031-9422(00)89804-0
557660 - Inula salsoloides: LTS0263103
102784 - Liatris elegans: 10.1080/14786410903027789
3398 - Magnoliopsida: LTS0263103
313936 - Pentanema: LTS0263103
119176 - Pentanema britannicum:
119176 - Pentanema britannicum: 10.1055/S-2005-873189
119176 - Pentanema britannicum: LTS0263103
125762 - Rhodanthe: LTS0263103
2529049 - Rhodanthe floribunda: 10.1016/0031-9422(89)80045-7
2529049 - Rhodanthe floribunda: LTS0263103
1142027 - Santolina pectinata: 10.1016/0031-9422(88)83058-9
1142031 - Santolina villosa: 10.1016/0031-9422(88)83058-9
55669 - Stevia: LTS0263103
35493 - Streptophyta: LTS0263103
684023 - Tithonia pedunculata: 10.1016/0031-9422(88)83040-1
58023 - Tracheophyta: LTS0263103
73317 - Viguiera: LTS0263103
1048925 - Viguiera hypargyrea: 10.1016/0031-9422(85)80038-8
1048925 - Viguiera hypargyrea: LTS0263103
33090 - Viridiplantae: LTS0263103

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

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]