nimbinin (BioDeep_00000395901)

 

Secondary id: BioDeep_00000267530

PANOMIX_OTCML-2023


代谢物信息卡片


17-(3-furyl)-4,4,10,13-tetramethyl-3,16-dioxo- 3,4,5,6,7,8,9,10,11,12,13,15,16,17-tetradecahydro-20- oxacyclopropa[14,15]cyclopenta[a]phenathren-7-yl acetate

化学式: C28H34O6 (466.2355264)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C45C(O4)C(=O)C(C5(CC3)C)C6=COC=C6)C)C)(C)C
InChI: InChI=1S/C28H34O6/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)22(31)23-28(26,34-23)27(17,20)6/h8-10,12,14,17-18,20-21,23H,7,11,13H2,1-6H3/t17-,18+,20-,21-,23-,25-,26+,27+,28-/m1/s1

描述信息

Epoxyazadiradione is a limonoid that is azadiradione with an epoxy group across positions 14 and 15. Isolated from Azadirachta indica it exhibits insecticidal activitry against mosquitoes. It has a role as an anti-inflammatory agent, an insecticide and a plant metabolite. It is an acetate ester, a cyclic terpene ketone, a member of furans, a limonoid, an epoxide and a pentacyclic triterpenoid. It is functionally related to an azadiradione.
Epoxyazadiradione is a natural product found in Azadirachta indica and Chisocheton siamensis with data available.
A limonoid that is azadiradione with an epoxy group across positions 14 and 15. Isolated from Azadirachta indica it exhibits insecticidal activitry against mosquitoes.
Epoxyazadiradione is a limonoid purified from neem (Azadirachta indica) fruits. Epoxyazadiradione inhibits the tautomerase activity of MIF of both human (huMIF) and malaria parasites (Plasmodium falciparum (PfMIF) and Plasmodium yoelii (PyMIF)) non-competitively in a reversible fashion (Ki, 2.11-5.23 μM). Epoxyazadiradione has the potential against proinflammatory reactions induced by MIF of both malaria parasites and human[1].

同义名列表

4 个代谢物同义名

17-(3-furyl)-4,4,10,13-tetramethyl-3,16-dioxo- 3,4,5,6,7,8,9,10,11,12,13,15,16,17-tetradecahydro-20- oxacyclopropa[14,15]cyclopenta[a]phenathren-7-yl acetate; (5alpha,7alpha,13alpha,14beta,15beta,17alpha)-17-(furan-3-yl)-4,4,8-trimethyl-3,16-dioxo-14,15-epoxyandrost-1-en-7-yl acetate; Epoxyazadiradione; nimbinin



数据库引用编号

7 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)

1 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

  • Siddavaram Nagini, Manikandan Palrasu, Anupam Bishayee. Limonoids from neem (Azadirachta Indica A. Juss.) are potential anticancer drug candidates. Medicinal research reviews. 2023 Aug; ?(?):. doi: 10.1002/med.21988. [PMID: 37589457]
  • Raghul Murugan, Ravi Rajesh, Ajay Guru, B Haridevamuthu, Bader O Almutairi, Mikhlid H Almutairi, Annie Juliet, S Renganayagi, Pushparathinam Gopinath, Jesu Arockiaraj. Deacetylepoxyazadiradione Derived from Epoxyazadiradione of Neem (Azadirachta indica A. Juss) Fruits Mitigates LPS-Induced Oxidative Stress and Inflammation in Zebrafish Larvae. Chemistry & biodiversity. 2022 Sep; 19(9):e202200041. doi: 10.1002/cbdv.202200041. [PMID: 36026548]
  • Sreerenjini Lakshmi, Jalaja Renjitha, Somappa B Sasidhar, Sulochana Priya. Epoxyazadiradione induced apoptosis/anoikis in triple-negative breast cancer cells, MDA-MB-231, by modulating diverse cellular effects. Journal of biochemical and molecular toxicology. 2021 Jun; 35(6):1-17. doi: 10.1002/jbt.22756. [PMID: 33684251]
  • Vipin Rai, Sushil Kumar Aggarwal, Sumit Singh Verma, Nikee Awasthee, Anupam Dhasmana, Sadhna Aggarwal, Satya N Das, Mangalam S Nair, Sanjay Yadav, Subash C Gupta. Epoxyazadiradione exhibit activities in head and neck squamous cell carcinoma by targeting multiple pathways. Apoptosis : an international journal on programmed cell death. 2020 10; 25(9-10):763-782. doi: 10.1007/s10495-020-01633-1. [PMID: 32894380]
  • G Shilpa, J Renjitha, R Saranga, Francis K Sajin, Mangalam S Nair, Beena Joy, B S Sasidhar, S Priya. Epoxyazadiradione Purified from the Azadirachta indica Seed Induced Mitochondrial Apoptosis and Inhibition of NFκB Nuclear Translocation in Human Cervical Cancer Cells. Phytotherapy research : PTR. 2017 Dec; 31(12):1892-1902. doi: 10.1002/ptr.5932. [PMID: 29044755]
  • Jie-Qing Liu, Cui-Fang Wang, Yan Li, Jian-Chao Chen, Lin Zhou, Ming-Hua Qiu. Limonoids from the leaves of Toona ciliata var. yunnanensis. Phytochemistry. 2012 Apr; 76(?):141-9. doi: 10.1016/j.phytochem.2012.01.002. [PMID: 22277739]
  • Giuseppina Chianese, Serge R Yerbanga, Leonardo Lucantoni, Annette Habluetzel, Nicoletta Basilico, Donatella Taramelli, Ernesto Fattorusso, Orazio Taglialatela-Scafati. Antiplasmodial triterpenoids from the fruits of neem, Azadirachta indica. Journal of natural products. 2010 Aug; 73(8):1448-52. doi: 10.1021/np100325q. [PMID: 20669933]
  • Hallur Gurulingappa, Vrushali Tare, Pushpa Pawar, Vijay Tungikar, Yogesh R Jorapur, Sriram Madhavi, Sujata V Bhat. Susceptibility of Aedes aegypti and Culex quinquefasciatus Larvae to gedunin-related limonoids. Chemistry & biodiversity. 2009 Jun; 6(6):897-902. doi: 10.1002/cbdv.200800105. [PMID: 19551731]
  • E Cohen, G B Quistad, J E Casida. Cytotoxicity of nimbolide, epoxyazadiradione and other limonoids from neem insecticide. Life sciences. 1996; 58(13):1075-81. doi: 10.1016/0024-3205(96)00061-6. [PMID: 8622560]