Silvestrol (BioDeep_00000395657)

 

Secondary id: BioDeep_00000183825, BioDeep_00001028696

PANOMIX_OTCML-2023


代谢物信息卡片


1H-Cyclopenta(b)benzofuran-2-carboxylic acid, 6-(((2S,3R,6R)-6-((1R)-1,2-dihydroxyethyl)-3-methoxy-1,4-dioxan-2-yl)oxy)-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-, methyl ester, (1R,2R,3S,3aR,8bS)-

化学式: C34H38O13 (654.2312297999999)
中文名称: Silvestrol, EPISILVESTROL, (1R,2R,3S,3AR,8BS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-二羟基乙基]-3-甲氧基-1,4-二氧己环-2-基]氧基]-2,3,3A,8B-四氢-1,8B-二羟基-8-甲氧基-3A-(4-甲氧基苯基)-3-苯基-1H-环戊烯并[B]苯并呋喃-2-羧酸甲酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 3.61%

分子结构信息

SMILES: COC1C(OC(CO1)C(CO)O)OC2=CC3=C(C(=C2)OC)C4(C(C(C(C4(O3)C5=CC=C(C=C5)OC)C6=CC=CC=C6)C(=O)OC)O)O
InChI: InChI=1S/C34H38O13/c1-40-20-12-10-19(11-13-20)34-27(18-8-6-5-7-9-18)26(30(38)42-3)29(37)33(34,39)28-23(41-2)14-21(15-24(28)47-34)45-32-31(43-4)44-17-25(46-32)22(36)16-35/h5-15,22,25-27,29,31-32,35-37,39H,16-17H2,1-4H3/t22-,25-,26-,27-,29-,31-,32-,33+,34+/m1/s1

描述信息

Silvestrol is an organic heterotricyclic compound that consists of a 2,3,3a,8b-tetrahydro-H-benzo[b]cyclopenta[d]furan framework substituted by hydroxy groups at positions C-1 and C-8b, a methoxycarbonyl group at C-2, a phenyl group at C-3, a 4-methoxyphenyl group at C-3a, a methoxy group at C-8 and a 1,4-dioxan-2-yloxy group at position C-6 which in turn is substituted by a methoxy group at position 3 and a 1,2-dihydroxyethyl group at position 6. Isolated from Aglaia silvestris, it exhibits antineoplastic activity. It has a role as a metabolite and an antineoplastic agent. It is an organic heterotricyclic compound, a member of dioxanes, an ether and a methyl ester.
Silvestrol is a natural product found in Aglaia foveolata and Aglaia silvestris with data available.
An organic heterotricyclic compound that consists of a 2,3,3a,8b-tetrahydro-H-benzo[b]cyclopenta[d]furan framework substituted by hydroxy groups at positions C-1 and C-8b, a methoxycarbonyl group at C-2, a phenyl group at C-3, a 4-methoxyphenyl group at C-3a, a methoxy group at C-8 and a 1,4-dioxan-2-yloxy group at position C-6 which in turn is substituted by a methoxy group at position 3 and a 1,2-dihydroxyethyl group at position 6. Isolated from Aglaia silvestris, it exhibits antineoplastic activity.

同义名列表

9 个代谢物同义名

1H-Cyclopenta(b)benzofuran-2-carboxylic acid, 6-(((2S,3R,6R)-6-((1R)-1,2-dihydroxyethyl)-3-methoxy-1,4-dioxan-2-yl)oxy)-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-, methyl ester, (1R,2R,3S,3aR,8bS)-; methyl (1R,2R,3S,3aR,8bS)-6-({(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl}oxy)-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxylate; methyl (1R,2R,3S,3aR,8bS)-6-[[(2S,3R,6R)-6-[(1R)-1,2-dihydroxyethyl]-3-methoxy-1,4-dioxan-2-yl]oxy]-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate; Silvestrol [WHO-DD]; UNII-KK3Y3KN5BV; (-)-silvestrol; Episilvestrol; Silvestrol; KK3Y3KN5BV



数据库引用编号

11 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)

2 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

  • Lu-Rong Yu, Xian-Zhong Han, Ying-Zi Tang, Dan Liu, Xian-Qin Luo, Xue-Wen Qiu, Jie Feng, Wen-Xiao Yuan, Jia-Yu Ding. Activation of the MEK/ERK Pathway Mediates the Inhibitory Effects of Silvestrol on Nasopharyngeal Carcinoma Cells via RAP1A, HK2, and GADD45A. Frontiers in bioscience (Landmark edition). 2024 Apr; 29(4):160. doi: 10.31083/j.fbl2904160. [PMID: 38682208]
  • Lorenzo Pedroni, Luca Dellafiora, Maria Olga Varrà, Gianni Galaverna, Sergio Ghidini. In silico study on the Hepatitis E virus RNA Helicase and its inhibition by silvestrol, rocaglamide and other flavagline compounds. Scientific reports. 2022 09; 12(1):15512. doi: 10.1038/s41598-022-19818-w. [PMID: 36109625]
  • J J David Ho, Tyler A Cunningham, Paola Manara, Caroline A Coughlin, Artavazd Arumov, Evan R Roberts, Ashanti Osteen, Preet Kumar, Daniel Bilbao, Jonathan R Krieger, Stephen Lee, Jonathan H Schatz. Proteomics reveal cap-dependent translation inhibitors remodel the translation machinery and translatome. Cell reports. 2021 10; 37(2):109806. doi: 10.1016/j.celrep.2021.109806. [PMID: 34644561]
  • Muhammad T Islam, Chandan Sarkar, Dina M El-Kersh, Sarmin Jamaddar, Shaikh J Uddin, Jamil A Shilpi, Mohammad S Mubarak. Natural products and their derivatives against coronavirus: A review of the non-clinical and pre-clinical data. Phytotherapy research : PTR. 2020 Oct; 34(10):2471-2492. doi: 10.1002/ptr.6700. [PMID: 32248575]
  • Canan G Nebigil, Christiane Moog, Stéphan Vagner, Nadia Benkirane-Jessel, Duncan R Smith, Laurent Désaubry. Flavaglines as natural products targeting eIF4A and prohibitins: From traditional Chinese medicine to antiviral activity against coronaviruses. European journal of medicinal chemistry. 2020 Oct; 203(?):112653. doi: 10.1016/j.ejmech.2020.112653. [PMID: 32693294]
  • Ziyad Tariq Muhseen, Guanglin Li. Promising Terpenes as Natural Antagonists of Cancer: An In-Silico Approach. Molecules (Basel, Switzerland). 2019 Dec; 25(1):. doi: 10.3390/molecules25010155. [PMID: 31906032]
  • Garima Agarwal, James R Wilson, Steven J Kurina, Gerardo D Anaya-Eugenio, Tran N Ninh, Joanna E Burdette, Djaja D Soejarto, Xiaolin Cheng, Esperanza J Carcache de Blanco, L Harinantenaina Rakotondraibe, A Douglas Kinghorn. Structurally Modified Cyclopenta[b]benzofuran Analogues Isolated from Aglaia perviridis. Journal of natural products. 2019 10; 82(10):2870-2877. doi: 10.1021/acs.jnatprod.9b00631. [PMID: 31621322]
  • Daniel Todt, Nora Moeller, Dimas Praditya, Volker Kinast, Martina Friesland, Michael Engelmann, Lieven Verhoye, Ibrahim M Sayed, Patrick Behrendt, Viet Loan Dao Thi, Philip Meuleman, Eike Steinmann. The natural compound silvestrol inhibits hepatitis E virus (HEV) replication in vitro and in vivo. Antiviral research. 2018 09; 157(?):151-158. doi: 10.1016/j.antiviral.2018.07.010. [PMID: 30036559]
  • Fabian Elgner, Catarina Sabino, Michael Basic, Daniela Ploen, Arnold Grünweller, Eberhard Hildt. Inhibition of Zika Virus Replication by Silvestrol. Viruses. 2018 03; 10(4):. doi: 10.3390/v10040149. [PMID: 29584632]
  • Christin Müller, Falk W Schulte, Kerstin Lange-Grünweller, Wiebke Obermann, Ramakanth Madhugiri, Stephan Pleschka, John Ziebuhr, Roland K Hartmann, Arnold Grünweller. Broad-spectrum antiviral activity of the eIF4A inhibitor silvestrol against corona- and picornaviruses. Antiviral research. 2018 02; 150(?):123-129. doi: 10.1016/j.antiviral.2017.12.010. [PMID: 29258862]
  • Yulin Ren, Wei-Lun Chen, Daniel D Lantvit, Ellen J Sass, Pratik Shriwas, Tran Ngoc Ninh, Hee-Byung Chai, Xiaoli Zhang, Djaja D Soejarto, Xiaozhuo Chen, David M Lucas, Steven M Swanson, Joanna E Burdette, A Douglas Kinghorn. Cardiac Glycoside Constituents of Streblus asper with Potential Antineoplastic Activity. Journal of natural products. 2017 03; 80(3):648-658. doi: 10.1021/acs.jnatprod.6b00924. [PMID: 27983842]
  • Nadine Biedenkopf, Kerstin Lange-Grünweller, Falk W Schulte, Aileen Weißer, Christin Müller, Dirk Becker, Stephan Becker, Roland K Hartmann, Arnold Grünweller. The natural compound silvestrol is a potent inhibitor of Ebola virus replication. Antiviral research. 2017 01; 137(?):76-81. doi: 10.1016/j.antiviral.2016.11.011. [PMID: 27864075]
  • Nuraqilah Othman, Li Pan, Michele Mejin, Julian C L Voong, Hee-byung Chai, Caroline M Pannell, A Douglas Kinghorn, Tiong C Yeo. Cyclopenta[b]benzofuran and Secodammarane Derivatives from the Stems of Aglaia stellatopilosa. Journal of natural products. 2016 Apr; 79(4):784-91. doi: 10.1021/acs.jnatprod.5b00810. [PMID: 26974604]
  • Wei-Lun Chen, Li Pan, A Douglas Kinghorn, Steven M Swanson, Joanna E Burdette. Silvestrol induces early autophagy and apoptosis in human melanoma cells. BMC cancer. 2016 Jan; 16(?):17. doi: 10.1186/s12885-015-1988-0. [PMID: 26762417]
  • Bill C Hawkins, Lisa M Lindqvist, Duong Nhu, Phillip P Sharp, David Segal, Andrew K Powell, Michael Campbell, Eileen Ryan, Jennifer M Chambers, Jonathan M White, Mark A Rizzacasa, Guillaume Lessene, David C S Huang, Christopher J Burns. Simplified silvestrol analogues with potent cytotoxic activity. ChemMedChem. 2014 Jul; 9(7):1556-66. doi: 10.1002/cmdc.201400024. [PMID: 24677741]
  • Sneha V Gupta, Ellen J Sass, Melanie E Davis, Ryan B Edwards, Gerard Lozanski, Nyla A Heerema, Amy Lehman, Xiaoli Zhang, David Jarjoura, John C Byrd, Li Pan, Kenneth K Chan, A Douglas Kinghorn, Mitch A Phelps, Michael R Grever, David M Lucas. Resistance to the translation initiation inhibitor silvestrol is mediated by ABCB1/P-glycoprotein overexpression in acute lymphoblastic leukemia cells. The AAPS journal. 2011 Sep; 13(3):357-64. doi: 10.1208/s12248-011-9276-7. [PMID: 21538216]
  • U V R Vijaya Saradhi, Sneha V Gupta, Ming Chiu, Jiang Wang, Yonghua Ling, Zhongfa Liu, David J Newman, Joseph M Covey, A Douglas Kinghorn, Guido Marcucci, David M Lucas, Michael R Grever, Mitch A Phelps, Kenneth K Chan. Characterization of silvestrol pharmacokinetics in mice using liquid chromatography-tandem mass spectrometry. The AAPS journal. 2011 Sep; 13(3):347-56. doi: 10.1208/s12248-011-9273-x. [PMID: 21499689]
  • Li Pan, Leonardus B S Kardono, Soedarsono Riswan, Heebyung Chai, Esperanza J Carcache de Blanco, Caroline M Pannell, Djaja Doel Soejarto, Thomas G McCloud, David J Newman, A Douglas Kinghorn. Isolation and characterization of minor analogues of silvestrol and other constituents from a large-scale re-collection of Aglaia foveolata. Journal of natural products. 2010 Nov; 73(11):1873-8. doi: 10.1021/np100503q. [PMID: 20939540]
  • David M Lucas, Patrick C Still, Lynette Bueno Pérez, Michael R Grever, A Douglas Kinghorn. Potential of plant-derived natural products in the treatment of leukemia and lymphoma. Current drug targets. 2010 Jul; 11(7):812-22. doi: 10.2174/138945010791320809. [PMID: 20370646]
  • David M Lucas, Ryan B Edwards, Gerard Lozanski, Derek A West, Jungook D Shin, Melissa A Vargo, Melanie E Davis, Darlene M Rozewski, Amy J Johnson, Bao-Ning Su, Virginia M Goettl, Nyla A Heerema, Thomas S Lin, Amy Lehman, Xiaoli Zhang, David Jarjoura, David J Newman, John C Byrd, A Douglas Kinghorn, Michael R Grever. The novel plant-derived agent silvestrol has B-cell selective activity in chronic lymphocytic leukemia and acute lymphoblastic leukemia in vitro and in vivo. Blood. 2009 May; 113(19):4656-66. doi: 10.1182/blood-2008-09-175430. [PMID: 19190247]