Convallatoxin (BioDeep_00000354555)

Main id: BioDeep_00000000881

 

natural product PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

化学式: C29H42O10 (550.2777832)
中文名称: 铃兰毒苷, K-毒毛旋花子配质-3-L-鼠李糖甙
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 9.09%

分子结构信息

SMILES: C(=O)(C=1)OCC1C(C(C)62)CCC(O)2C(C5)([H])C(CC6)([H])C(C3)(C(O)(C5)CC(OC(C(O)4)(OC(C)C(O)C4O)[H])C3)C=O
InChI: InChI=1S/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15-,17-,18+,19-,20+,22-,23+,24+,25-,26+,27-,28-,29-/m0/s1

描述信息

Convallatoxin is a cardenolide glycoside that consists of strophanthidin having a 6-deoxy-alpha-L-mannopyranosyl (L-rhamnosyl) group attached at position 3. It has a role as a vasodilator agent and a metabolite. It is an alpha-L-rhamnoside, a 19-oxo steroid, a 14beta-hydroxy steroid, a 5beta-hydroxy steroid, a steroid lactone and a steroid aldehyde. It is functionally related to a strophanthidin.
Convallatoxin is a natural product found in Crossosoma bigelovii, Convallaria keiskei, and other organisms with data available.
Convallatoxin is a glycoside extracted from Convallaria majalis. Convallatoxin is also isolated from the trunk bark of Antiaris toxicaria (A15340).
A cardenolide glycoside that consists of strophanthidin having a 6-deoxy-alpha-L-mannopyranosyl (L-rhamnosyl) group attached at position 3.
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D013328 - Strophanthins
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
Convallatoxin is a cardiac glycoside isolated from Adonis amurensis Regel et Radde. Convallatoxin ameliorates colitic inflammation via activation of PPARγ and suppression of NF-κB. Convallatoxin is a P-glycoprotein (P-gp) substrate and recognized Val982 as an important amino acid involved in its transport. Convallatoxin is an enhancer of ligand-induced MOR endocytosis with high potency and efficacy. Anti-inflammatory and anti-proliferative properties[1][2][3].
Convallatoxin is a cardiac glycoside isolated from Adonis amurensis Regel et Radde. Convallatoxin ameliorates colitic inflammation via activation of PPARγ and suppression of NF-κB. Convallatoxin is a P-glycoprotein (P-gp) substrate and recognized Val982 as an important amino acid involved in its transport. Convallatoxin is an enhancer of ligand-induced MOR endocytosis with high potency and efficacy. Anti-inflammatory and anti-proliferative properties[1][2][3].

同义名列表

35 个代谢物同义名

(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde; (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde; (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2,5-dihydrofuran-3-yl)-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde; CARD-20(22)-ENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-5,14-DIHYDROXY-19-OXO-, (3.BETA.,5.BETA.)-; Card-20(22)-enolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-, (3beta,5beta)-; (3beta,5beta)-3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-card-20(22)-enolide; 3beta-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-5,14-dihydroxy-19-oxo-5beta-card-20(22)-enolide; 3beta-(6-deoxy-alpha-L-mannopyranosyloxy)-5,14-dihydroxy-19-oxo-5beta-card-20(22)-enolide; 5beta,14beta-Dihydroxy-19-oxo-3beta[(alpha-L-rhamnopyranosyl)oxy]card-20,22-enolide; 3beta-(alpha-L-rhamnopyranosyloxy)-5,14-dihydroxy-19-oxo-5beta-card-20(22)-enolide; Card-20(22)-enolide, 3-[(6-deoxyhexopyranosyl)oxy]-5,14-dihydroxy-19-oxo-; Mannopyranoside, strophanthidin-3,6-deoxy-, alpha-L-; Strophanthidin, 3-(6-deoxy-alpha-L-mannopyranoside); Rhamnoside, strophanthidin-3, alpha-L-; Strophanthidin 3-O-alpha-L-rhamnoside; STROPHANTHIDIN .ALPHA.-L-RHAMNOSIDE; strophanthidin-alpha-L-rhamnoside; Strophanthidin alpha-L-rhamnoside; CONVALLATOXIN [WHO-DD]; Convallatoxin, >=65\\%; CONVALLATOXIN [MI]; Convallatoxoside; Convallaotoxin; Convallotoxin; Convallatoxin; Convallopan; Convallaton; corglycone; Convalpur; Korglykon; korglycon; corglycon; Corglykon; Convapur; Convallatoxin



数据库引用编号

41 个数据库交叉引用编号

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代谢反应

0 个相关的代谢反应过程信息。

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64 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

  • Yue Xing, Jing Ying Wang, Ming Yue Li, Zhi Hong Zhang, Hong Lan Jin, Hong Xiang Zuo, Juan Ma, Xuejun Jin. Convallatoxin inhibits IL-1β production by suppressing zinc finger protein 91 (ZFP91)-mediated pro-IL-1β ubiquitination and caspase-8 inflammasome activity. British journal of pharmacology. 2022 05; 179(9):1887-1907. doi: 10.1111/bph.15758. [PMID: 34825365]
  • Yi Zhang, Xiujin Shi, Jialun Han, Wenxing Peng, Zhenwei Fang, Yang Zhou, Xiaoyu Xu, Jie Lin, Fucheng Xiao, Limin Zhao, Yang Lin. Convallatoxin Promotes M2 Macrophage Polarization to Attenuate Atherosclerosis Through PPARγ-Integrin αvβ5 Signaling Pathway. Drug design, development and therapy. 2021; 15(?):803-812. doi: 10.2147/dddt.s288728. [PMID: 33654384]
  • Bo-Wen Jiang, Wen-Jing Zhang, Ying Wang, Li-Ping Tan, Yong-Li Bao, Zhen-Bo Song, Chun-Lei Yu, Shu-Yue Wang, Lei Liu, Yu-Xin Li. Convallatoxin induces HaCaT cell necroptosis and ameliorates skin lesions in psoriasis-like mouse models. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Jan; 121(?):109615. doi: 10.1016/j.biopha.2019.109615. [PMID: 31707343]
  • Amitava Dasgupta, Laverne Bourgeois. Convallatoxin, the active cardiac glycoside of lily of the valley, minimally affects the ADVIA Centaur digoxin assay. Journal of clinical laboratory analysis. 2018 Oct; 32(8):e22583. doi: 10.1002/jcla.22583. [PMID: 29855084]
  • Naira Fernanda Zanchett Schneider, Izabella Thais Silva, Lara Persich, Annelise de Carvalho, Sayonarah C Rocha, Lucas Marostica, Ana Carolina Pacheco Ramos, Alex G Taranto, Rodrigo M Pádua, Wolfgang Kreis, Leandro A Barbosa, Fernão C Braga, Cláudia M O Simões. Cytotoxic effects of the cardenolide convallatoxin and its Na,K-ATPase regulation. Molecular and cellular biochemistry. 2017 Apr; 428(1-2):23-39. doi: 10.1007/s11010-016-2914-8. [PMID: 28176244]
  • Jamie M Everett, Yumi A Kojima, Barbara Davis, Amer Wahed, Amitava Dasgupta. The iDigoxin Assay is More Sensitive than LOCI Digoxin Assay for Rapid Detection of Convallatoxin, the Active Cardiac Glycoside of Lily of The Valley. Annals of clinical and laboratory science. 2015; 45(3):323-6. doi: . [PMID: 26116597]
  • Elnaz Gozalpour, Rick Greupink, Albert Bilos, Vivienne Verweij, Jeroen J M W van den Heuvel, Rosalinde Masereeuw, Frans G M Russel, Jan B Koenderink. Convallatoxin: a new P-glycoprotein substrate. European journal of pharmacology. 2014 Dec; 744(?):18-27. doi: 10.1016/j.ejphar.2014.09.031. [PMID: 25264938]
  • Kerry J Welsh, Richard Sheng Poe Huang, Jeffrey K Actor, Amitava Dasgupta. Rapid detection of the active cardiac glycoside convallatoxin of lily of the valley using LOCI digoxin assay. American journal of clinical pathology. 2014 Sep; 142(3):307-12. doi: 10.1309/ajcpcoxf0o5xxtkd. [PMID: 25125619]
  • S L Fink, T E Robey, A F Tarabar, M E Hodsdon. Rapid detection of convallatoxin using five digoxin immunoassays. Clinical toxicology (Philadelphia, Pa.). 2014 Aug; 52(7):659-63. doi: 10.3109/15563650.2014.932366. [PMID: 24980812]
  • Li-Shian Shi, Sheng-Chu Kuo, Han-Dong Sun, Susan L Morris-Natschke, Kuo-Hsiung Lee, Tian-Shung Wu. Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria. Bioorganic & medicinal chemistry. 2014 Mar; 22(6):1889-98. doi: 10.1016/j.bmc.2014.01.052. [PMID: 24582402]
  • Qian Liu, Jin-Shan Tang, Meng-Jie Hu, Jie Liu, Hai-Feng Chen, Hao Gao, Guang-Hui Wang, Shun-Lin Li, Xiao-Jiang Hao, Xiao-Kun Zhang, Xin-Sheng Yao. Antiproliferative cardiac glycosides from the latex of Antiaris toxicaria. Journal of natural products. 2013 Sep; 76(9):1771-80. doi: 10.1021/np4005147. [PMID: 24033101]
  • Heidrun Weidemann. 'The Lower Threshold' phenomenon in tumor cells toward endogenous digitalis-like compounds: Responsible for tumorigenesis?. Journal of carcinogenesis. 2012; 11(?):2. doi: 10.4103/1477-3163.92999. [PMID: 22438768]
  • Li-Shian Shi, Yu-Ren Liao, Ming-Jai Su, An-Sheng Lee, Ping-Chung Kuo, Amooru G Damu, Sheng-Chu Kuo, Han-Dong Sun, Kuo-Hsiung Lee, Tian-Shung Wu. Cardiac glycosides from Antiaris toxicaria with potent cardiotonic activity. Journal of natural products. 2010 Jul; 73(7):1214-22. doi: 10.1021/np9005212. [PMID: 20553004]
  • Jenny Felth, Linda Rickardson, Josefin Rosén, Malin Wickström, Mårten Fryknäs, Magnus Lindskog, Lars Bohlin, Joachim Gullbo. Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs. Journal of natural products. 2009 Nov; 72(11):1969-74. doi: 10.1021/np900210m. [PMID: 19894733]
  • Paul Klausmeyer, Qin Zhou, Dominic A Scudiero, Badarch Uranchimeg, Giovanni Melillo, John H Cardellina, Robert H Shoemaker, Ching-Jer Chang, Thomas G McCloud. Cytotoxic and HIF-1alpha inhibitory compounds from Crossosoma bigelovii. Journal of natural products. 2009 May; 72(5):805-12. doi: 10.1021/np8006342. [PMID: 19405508]
  • Deok Ho Choi, Dae Gill Kang, Xun Cui, Kyung Woo Cho, Eun Jin Sohn, Jin Sook Kim, Ho Sub Lee. The positive inotropic effect of the aqueous extract of Convallaria keiskei in beating rabbit atria. Life sciences. 2006 Aug; 79(12):1178-85. doi: 10.1016/j.lfs.2006.03.019. [PMID: 16616766]
  • A D Patil, P W Baures, D S Eggleston, L Faucette, M E Hemling, J W Westley, R K Johnson. A screen for inhibitors of DNA recombination: identification of two new spirostanol glycosides from Chamaedorea linearis. Journal of natural products. 1993 Sep; 56(9):1451-8. doi: 10.1021/np50099a003. [PMID: 8254345]
  • H D Lehmann. [Effect of plant glycosides on resistance and capacitance vessels]. Arzneimittel-Forschung. 1984; 34(4):423-9. doi: . [PMID: 6540100]