Withanone (BioDeep_00000395651)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,15-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

化学式: C28H38O6 (470.2668)
中文名称: WITHANONE
谱图信息: 最多检出来源 Viridiplantae(plant) 100%

分子结构信息

SMILES: CC(C1CC(C)=C(C)C(=O)O1)C1(O)CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C
InChI: InChI=1S/C28H38O6/c1-14-13-19(33-24(30)15(14)2)16(3)27(31)12-9-17-21-18(8-11-25(17,27)4)26(5)20(29)7-6-10-28(26,32)23-22(21)34-23/h6-7,16-19,21-23,31-32H,8-13H2,1-5H3

描述信息

Annotation level-1
Withanone is a natural product found in Withania somnifera, Physalis philadelphica, and Discopodium penninervium with data available.

同义名列表

9 个代谢物同义名

Withanone; (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,15-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one; 15-[1-(4,5-Dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-5,15-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one; (5.ALPHA.,6.ALPHA.,7.ALPHA.,22R)-5,17-DIHYDROXY-6,7:22,26-DIEPOXYERGOSTA-2,24-DIENE-1,26-DIONE; (5alpha,6alpha,7alpha,22R)-5,17-Dihydroxy-6,7:22,26-diepoxyergosta-2,24-diene-1,26-dione; 6,7-epoxy-5,17-dihydroxy-1-oxowitha-2,24-dienolide; (22R)-5alpha,17alpha-Dihydroxy-6alpha,7alpha; Withanone, analytical standard; Withanone(sh)



数据库引用编号

21 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)

23 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

  • Vipul Kumar, Jaspreet Kaur Dhanjal, Priyanshu Bhargava, Ashish Kaul, Jia Wang, Huayue Zhang, Sunil C Kaul, Renu Wadhwa, Durai Sundar. Withanone and Withaferin-A are predicted to interact with transmembrane protease serine 2 (TMPRSS2) and block entry of SARS-CoV-2 into cells. Journal of biomolecular structure & dynamics. 2022 01; 40(1):1-13. doi: 10.1080/07391102.2020.1775704. [PMID: 32469279]
  • Jia Wang, Huayue Zhang, Ashish Kaul, Kejuan Li, Didik Priyandoko, Sunil C Kaul, Renu Wadhwa. Effect of Ashwagandha Withanolides on Muscle Cell Differentiation. Biomolecules. 2021 10; 11(10):. doi: 10.3390/biom11101454. [PMID: 34680087]
  • Janine Naß, Thomas Efferth. Withanone Ameliorates Stress Symptoms in Caenorhabditis Elegans by Acting through Serotonin Receptors. Pharmacopsychiatry. 2021 Sep; 54(5):215-223. doi: 10.1055/a-1349-3870. [PMID: 33957677]
  • Vipul Kumar, Jaspreet Kaur Dhanjal, Sunil C Kaul, Renu Wadhwa, Durai Sundar. Withanone and caffeic acid phenethyl ester are predicted to interact with main protease (Mpro) of SARS-CoV-2 and inhibit its activity. Journal of biomolecular structure & dynamics. 2021 07; 39(11):3842-3854. doi: 10.1080/07391102.2020.1772108. [PMID: 32431217]
  • Sandeep K Singh, Guru R Valicherla, Anil K Bikkasani, Srikanth H Cheruvu, Zakir Hossain, Isha Taneja, Hafsa Ahmad, Kanumuri S R Raju, Neelam S Sangwan, Shio K Singh, Anil K Dwivedi, Mohammad Wahajuddin, Jiaur R Gayen. Elucidation of plasma protein binding, blood partitioning, permeability, CYP phenotyping and CYP inhibition studies of Withanone using validated UPLC method: An active constituent of neuroprotective herb Ashwagandha. Journal of ethnopharmacology. 2021 Apr; 270(?):113819. doi: 10.1016/j.jep.2021.113819. [PMID: 33460762]
  • Acharya Balkrishna, Subarna Pokhrel, Hoshiyar Singh, Monali Joshi, Vallabh Prakash Mulay, Swati Haldar, Anurag Varshney. Withanone from Withania somnifera Attenuates SARS-CoV-2 RBD and Host ACE2 Interactions to Rescue Spike Protein Induced Pathologies in Humanized Zebrafish Model. Drug design, development and therapy. 2021; 15(?):1111-1133. doi: 10.2147/dddt.s292805. [PMID: 33737804]
  • Sil Kim, Jae Sik Yu, Ji Young Lee, Sang Un Choi, Jeongmi Lee, Ki Hyun Kim. Cytotoxic Withanolides from the Roots of Indian Ginseng ( Withania somnifera). Journal of natural products. 2019 04; 82(4):765-773. doi: 10.1021/acs.jnatprod.8b00665. [PMID: 30776236]
  • Kasmika Borah, Sanchita Sharma, Yumnam Silla. Structural bioinformatics-based identification of putative plant based lead compounds for Alzheimer Disease Therapy. Computational biology and chemistry. 2019 Feb; 78(?):359-366. doi: 10.1016/j.compbiolchem.2018.12.012. [PMID: 30677568]
  • Anjali Pandey, Sarang Bani, Prabhu Dutt, Naresh Kumar Satti, Krishan Avtar Suri, Ghulam Nabi Qazi. Multifunctional neuroprotective effect of Withanone, a compound from Withania somnifera roots in alleviating cognitive dysfunction. Cytokine. 2018 02; 102(?):211-221. doi: 10.1016/j.cyto.2017.10.019. [PMID: 29108796]
  • Amandeep Kaur, Baldev Singh, Puja Ohri, Jia Wang, Renu Wadhwa, Sunil C Kaul, Pratap Kumar Pati, Arvinder Kaur. Organic cultivation of Ashwagandha with improved biomass and high content of active Withanolides: Use of Vermicompost. PloS one. 2018; 13(4):e0194314. doi: 10.1371/journal.pone.0194314. [PMID: 29659590]
  • Nawab John Dar, Javeed Ahmad Bhat, Naresh Kumar Satti, Parduman Raj Sharma, Abid Hamid, Muzamil Ahmad. Withanone, an Active Constituent from Withania somnifera, Affords Protection Against NMDA-Induced Excitotoxicity in Neuron-Like Cells. Molecular neurobiology. 2017 09; 54(7):5061-5073. doi: 10.1007/s12035-016-0044-7. [PMID: 27541286]
  • Seema Ahlawat, Parul Saxena, Athar Ali, Shazia Khan, Malik Z Abdin. Comparative study of withanolide production and the related transcriptional responses of biosynthetic genes in fungi elicited cell suspension culture of Withania somnifera in shake flask and bioreactor. Plant physiology and biochemistry : PPB. 2017 May; 114(?):19-28. doi: 10.1016/j.plaphy.2017.02.013. [PMID: 28249222]
  • V Singh, B Singh, A Sharma, K Kaur, A P Gupta, R K Salar, V Hallan, P K Pati. Leaf spot disease adversely affects human health-promoting constituents and withanolide biosynthesis in Withania somnifera (L.) Dunal. Journal of applied microbiology. 2017 Jan; 122(1):153-165. doi: 10.1111/jam.13314. [PMID: 27709727]
  • Syed Saema, Laiq Ur Rahman, Ruchi Singh, Abhishek Niranjan, Iffat Zareen Ahmad, Pratibha Misra. Ectopic overexpression of WsSGTL1, a sterol glucosyltransferase gene in Withania somnifera, promotes growth, enhances glycowithanolide and provides tolerance to abiotic and biotic stresses. Plant cell reports. 2016 Jan; 35(1):195-211. doi: 10.1007/s00299-015-1879-5. [PMID: 26518426]
  • Sunil C Kaul, Yoshiyuki Ishida, Kazuya Tamura, Teruo Wada, Tomoko Iitsuka, Sukant Garg, Mijung Kim, Ran Gao, Shoichi Nakai, Youji Okamoto, Keiji Terao, Renu Wadhwa. Novel Methods to Generate Active Ingredients-Enriched Ashwagandha Leaves and Extracts. PloS one. 2016; 11(12):e0166945. doi: 10.1371/journal.pone.0166945. [PMID: 27936030]
  • Ran Gao, Navjot Shah, Jung-Sun Lee, Shashank P Katiyar, Ling Li, Eonju Oh, Durai Sundar, Chae-Ok Yun, Renu Wadhwa, Sunil C Kaul. Withanone-rich combination of Ashwagandha withanolides restricts metastasis and angiogenesis through hnRNP-K. Molecular cancer therapeutics. 2014 Dec; 13(12):2930-40. doi: 10.1158/1535-7163.mct-14-0324. [PMID: 25236891]
  • Pallavi Joshi, Laxminarain Misra, Amreen A Siddique, Monica Srivastava, Shiv Kumar, Mahendra P Darokar. Epoxide group relationship with cytotoxicity in withanolide derivatives from Withania somnifera. Steroids. 2014 Jan; 79(?):19-27. doi: 10.1016/j.steroids.2013.10.008. [PMID: 24184562]
  • Farzana Sabir, Smrati Mishra, Rajender S Sangwan, Jyoti S Jadaun, Neelam S Sangwan. Qualitative and quantitative variations in withanolides and expression of some pathway genes during different stages of morphogenesis in Withania somnifera Dunal. Protoplasma. 2013 Apr; 250(2):539-49. doi: 10.1007/s00709-012-0438-y. [PMID: 22878597]
  • Ganeshan Sivanandhan, Manoharan Rajesh, Muthukrishnan Arun, Murugaraj Jeyaraj, Gnanajothi Kapil Dev, Markandan Manickavasagam, Natesan Selvaraj, Andy Ganapathi. Optimization of carbon source for hairy root growth and withaferin A and withanone production in Withania somnifera. Natural product communications. 2012 Oct; 7(10):1271-2. doi: ". [PMID: 23156987]
  • Kirti Vaishnavi, Nishant Saxena, Navjot Shah, Rumani Singh, Kavyashree Manjunath, M Uthayakumar, Shankar P Kanaujia, Sunil C Kaul, Kanagaraj Sekar, Renu Wadhwa. Differential activities of the two closely related withanolides, Withaferin A and Withanone: bioinformatics and experimental evidences. PloS one. 2012; 7(9):e44419. doi: 10.1371/journal.pone.0044419. [PMID: 22973447]
  • Abhinav Grover, Rumani Singh, Ashutosh Shandilya, Didik Priyandoko, Vibhuti Agrawal, Virendra S Bisaria, Renu Wadhwa, Sunil C Kaul, Durai Sundar. Ashwagandha derived withanone targets TPX2-Aurora A complex: computational and experimental evidence to its anticancer activity. PloS one. 2012; 7(1):e30890. doi: 10.1371/journal.pone.0030890. [PMID: 22303466]
  • Didik Priyandoko, Tetsuro Ishii, Sunil C Kaul, Renu Wadhwa. Ashwagandha leaf derived withanone protects normal human cells against the toxicity of methoxyacetic acid, a major industrial metabolite. PloS one. 2011 May; 6(5):e19552. doi: 10.1371/journal.pone.0019552. [PMID: 21573189]
  • Arpita Konar, Navjot Shah, Rumani Singh, Nishant Saxena, Sunil C Kaul, Renu Wadhwa, Mahendra K Thakur. Protective role of Ashwagandha leaf extract and its component withanone on scopolamine-induced changes in the brain and brain-derived cells. PloS one. 2011; 6(11):e27265. doi: 10.1371/journal.pone.0027265. [PMID: 22096544]