Azadiradione (BioDeep_00000231366)

   

PANOMIX_OTCML-2023 Chemicals and Drugs natural product


代谢物信息卡片


[(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate

化学式: C28H34O5 (450.2406)
中文名称: 印苦楝二酮
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 97.16%

分子结构信息

SMILES: C1=C[C@]2([C@@H](C(C1=O)(C)C)C[C@H]([C@@]1([C@@H]2CC[C@@]2(C1=CC(=O)[C@H]2c1cocc1)C)C)OC(=O)C)C
InChI: InChI=1S/C28H34O5/c1-16(29)33-23-14-20-25(2,3)22(31)8-11-26(20,4)19-7-10-27(5)21(28(19,23)6)13-18(30)24(27)17-9-12-32-15-17/h8-9,11-13,15,19-20,23-24H,7,10,14H2,1-6H3/t19-,20+,23-,24-,26-,27-,28-/m1/s1

描述信息

Azadiradione is a tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by oxo groups at positions 3 and 16, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antimycobacterial and anti-inflammatory activities. It has a role as a plant metabolite, an antimycobacterial drug and an anti-inflammatory agent. It is a limonoid, a tetracyclic triterpenoid, an acetate ester, a cyclic terpene ketone and a member of furans.
Azadiradione is a natural product found in Azadirachta indica, Cedrela odorata, and other organisms with data available.
A tetracyclic triterpenoid that is 4,4,8-trimethylandrosta-1,14-diene substituted by oxo groups at positions 3 and 16, an acetoxy group at position 7 and a furan-3-yl group at position 17. Isolated from Azadirachta indica, it exhibits antimycobacterial and anti-inflammatory activities.

同义名列表

4 个代谢物同义名

[(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] acetate; 24-Nor-5alpha,13alpha,17alpha-chola-1,14,20,22-tetraene-3,16-dione, 21,23-epoxy-7alpha-hydroxy-4,4,8-trimethyl-,acetate; (5alpha,7alpha,13alpha,17alpha)-17-(furan-3-yl)-4,4,8-trimethyl-3,16-dioxoandrosta-1,14-dien-7-yl acetate; Azadiradione



数据库引用编号

10 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)

41 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


文献列表

  • Sudipta Jana, Bhaskarjyoti Giri, Sagarika Das, Anirban Manna, Subhash C Mandal, Nihar Ranjan Jana. Azadiradione up-regulates the expression of parvalbumin and BDNF via Ube3a. Gene. 2024 Mar; 897(?):148081. doi: 10.1016/j.gene.2023.148081. [PMID: 38101713]
  • 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]
  • Quan Gao, Jia Sun, Hang Xun, Xi Yao, Jin Wang, Feng Tang. A new azadirachta from the crude extracts of neem (Azadirachta Indica A. Juss) seeds. Natural product research. 2017 Aug; 31(15):1739-1746. doi: 10.1080/14786419.2017.1290616. [PMID: 28278641]
  • Vinod K Nelson, Asif Ali, Naibedya Dutta, Suvranil Ghosh, Manas Jana, Arnab Ganguli, Andrei Komarov, Soumyadip Paul, Vibha Dwivedi, Subhrangsu Chatterjee, Nihar R Jana, Subhash C Lakhotia, Gopal Chakrabarti, Anup K Misra, Subhash C Mandal, Mahadeb Pal. Azadiradione ameliorates polyglutamine expansion disease in Drosophila by potentiating DNA binding activity of heat shock factor 1. Oncotarget. 2016 Nov; 7(48):78281-78296. doi: 10.18632/oncotarget.12930. [PMID: 27835876]
  • Rohit Singh, Vaibhav Mishra, Sukanya Pandeti, Gautam Palit, Manoj K Barthwal, Haushila Prasad Pandey, Tadigoppula Narender. Cytoprotective and Anti-secretory Effects of Azadiradione Isolated from the Seeds of Azadirachta indica (neem) on Gastric Ulcers in Rat Models. Phytotherapy research : PTR. 2015 Jun; 29(6):910-6. doi: 10.1002/ptr.5332. [PMID: 25851068]
  • Sudha Ponnusamy, Saikat Haldar, Fayaj Mulani, Smita Zinjarde, Hirekodathakallu Thulasiram, Ameeta RaviKumar. Gedunin and Azadiradione: Human Pancreatic Alpha-Amylase Inhibiting Limonoids from Neem (Azadirachta indica) as Anti-Diabetic Agents. PloS one. 2015; 10(10):e0140113. doi: 10.1371/journal.pone.0140113. [PMID: 26469405]
  • K Ilango, G Maharajan, S Narasimhan. Anti-nociceptive and anti-inflammatory activities of Azadirachta indica fruit skin extract and its isolated constituent azadiradione. Natural product research. 2013; 27(16):1463-7. doi: 10.1080/14786419.2012.717288. [PMID: 22928548]
  • 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]