Deslanoside (BioDeep_00000017471)

 

Secondary id: BioDeep_00000597197, BioDeep_00000866774

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs Volatile Flavor Compounds natural product


代谢物信息卡片


4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-5-{[(2R,4S,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one

化学式: C47H74O19 (942.4824054000001)
中文名称: 去乙酰西地兰, 去乙酰毛花苷, 毛花强心丙, 毛地黄苷C, 去乙酰毛花苷丙
谱图信息: 最多检出来源 Homo sapiens(blood) 9.68%

分子结构信息

SMILES: CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CC(C5(C4(CCC5C6=CC(=O)OC6)O)C)O)C)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)O)O
InChI: InChI=1S/C47H74O19/c1-20-41(64-36-16-30(50)42(21(2)60-36)65-37-17-31(51)43(22(3)61-37)66-44-40(56)39(55)38(54)32(18-48)63-44)29(49)15-35(59-20)62-25-8-10-45(4)24(13-25)6-7-27-28(45)14-33(52)46(5)26(9-11-47(27,46)57)23-12-34(53)58-19-23/h12,20-22,24-33,35-44,48-52,54-57H,6-11,13-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27-,28+,29+,30+,31+,32-,33-,35+,36+,37+,38-,39+,40-,41-,42-,43-,44+,45+,46+,47+/m1/s1

描述信息

Deslanoside is a cardenolide glycoside that is lanatoside C with the acetoxy group replaced by a hydroxy group. It has a role as an anti-arrhythmia drug, a cardiotonic drug, a metabolite and an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It is a 14beta-hydroxy steroid, a 12beta-hydroxy steroid, a cardenolide glycoside and a tetrasaccharide derivative.
Deacetyllanatoside C. A cardiotonic glycoside from the leaves of Digitalis lanata.
Deslanoside is a natural product found in Digitalis parviflora, Digitalis viridiflora, and other organisms with data available.
Deacetyllanatoside C. A cardiotonic glycoside from the leaves of Digitalis lanata.
Deslanoside is only found in individuals that have used or taken this drug. It is a cardiotonic glycoside from the leaves of Digitalis lanata. [PubChem]Deslanoside inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Deslanoside also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.
C - Cardiovascular system > C01 - Cardiac therapy > C01A - Cardiac glycosides > C01AA - Digitalis glycosides
A cardenolide glycoside that is lanatoside C with the acetoxy group replaced by a hydroxy group.
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D004071 - Digitalis Glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
C78274 - Agent Affecting Cardiovascular System > C78322 - Cardiotonic Agent
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
D004791 - Enzyme Inhibitors
Deslanoside (Desacetyllanatoside C) is a rapidly acting cardiac glycoside used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation. Deslanoside inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations [1][2][3].
Deslanoside (Desacetyllanatoside C) is a rapidly acting cardiac glycoside used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation. Deslanoside inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations [1][2][3].

同义名列表

74 个代谢物同义名

4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-5-{[(2R,4S,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one; CARD-20(22)-ENOLIDE, 3-((O-.BETA.-D-GLUCOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-O-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL-(1->4)-2,6-DIDEOXY-.BETA.-D-RIBO-HEXOPYRANOSYL)OXY)-12,14-DIHYDROXY-, (3.BETA.,5.BETA.,12.BETA.)-; Card-20(22)-enolide, 3-((O-beta-D-glucopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3beta,5beta,12beta)-; 3-[(O-beta-D-glucopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide; Card-20(22)-enolide, 3-((O-beta-D-glucopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3beta,5beta,12beta)-; 3-[(O-beta-D-glucopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide; 3-((O-beta-D-glucopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide; (3beta,5beta,12beta)-3-{[beta-D-glucopyranosyl-(1-->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide; (3beta,5beta,12beta)-3-((beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxycard-20(22)-enolide; (3beta,5beta,12beta)-3-{[beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide; 3beta-(beta-D-Glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyloxy)-12beta,14-dihydroxy-5beta,14beta-card-20(22)-enolide; 3beta-{[beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12beta,14-dihydroxy-5beta-card-20(22)-enolide; 3beta-((beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12beta,14-dihydroxy-5beta-card-20(22)-enolide; 3-[(O-Β-D-glucopyranosyl-(1->4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3β,5β,12β-card-20(22)-enolide; 3-[(O-b-D-Glucopyranosyl-(1->4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3b,5b,12b-card-20(22)-enolide; (3b,5b,12b)-3-{[b-D-glucopyranosyl-(1->4)-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-b-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide; (3Β,5β,12β)-3-{[β-D-glucopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide; 3beta-(O-beta-D-Glucopyranosyl-(1-4)-O-beta-D-digitoxosyl-(1-4)-O-beta-D-digitoxosyl-(1-4)-beta-D-digitoxosyloxy-12beta,14-dihydroxy-5beta,14beta-card-20(22)-enolid; 4-18-00-02455 (Beilstein Handbook Reference); Deacetyllanatoside C;Desacetyllanatoside C; Deslanoside (USP:INN:BAN:JAN); Deslanoside [USP:INN:BAN:JAN]; OBATZBGFDSVCJD-LALPQLPRSA-N; DESLANOSIDE (EP MONOGRAPH); DESLANOSIDE [USP IMPURITY]; Deslanoside (JP17/USP/INN); DESLANOSIDE (USP IMPURITY); DESLANOSIDE [EP MONOGRAPH]; Deslanosido [INN-Spanish]; Deslanosido (INN-Spanish); DESLANOSIDE [ORANGE BOOK]; Deslanosidum (INN-Latin); Deslanosidum [INN-Latin]; Lanatoside C, deacetyl-; Desacetyl-Lanatoside C; C, Desacetyllanatoside; C, Desacetyldigilanide; Desacetyllanatoside C; Deacetyl-lanatoside C; Lanatoside, Desacetyl; Desacetyldigilanide C; DESLANOSIDE [USP-RS]; DESLANOSIDE (USP-RS); DESLANOSIDE [WHO-DD]; Deacetyllanatoside C; Desacetyl Lanatoside; DESLANOSIDE (MART.); DESLANOSIDE [MART.]; Deacetylanatoside C; DESLANOSIDE [VANDF]; DESLANOSIDE [JAN]; DESLANOSIDE [INN]; C, Deslanatoside; Cedilanid-d (TN); DESLANOSIDE [MI]; Deslanatoside C; Deslanosidum C; Tox21_111671_1; glucodigoxin; Deslanosidum; Tox21_111671; Deslanoside; Cedilanid-D; Deslanosido; Cedilanid D; Sediranido; CedilanidD; Deslanosid; Cedilanide; Lekozid; C01AA07; Desace; NSC7531; Deslanoside



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

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PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

29 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

  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Rong Xiao, Yue-sheng Huang, Ze-yuan Lei, Jing Ruan. [Effects of single or combined administration of cedilanid and enalaprilat on visceral damages in early stage of severe scald in rats]. Zhonghua shao shang za zhi = Zhonghua shaoshang zazhi = Chinese journal of burns. 2008 Dec; 24(6):428-31. doi: . [PMID: 19149943]
  • Wayne L Miller, Kent R Bailey, Susan A Weston, John C Burnett, Richard J Rodeheffer. Hemodynamic and plasma atrial natriuretic peptide responses to acute digitalis therapy in patients with normal and impaired left ventricular function. European journal of heart failure. 2002 Jan; 4(1):63-72. doi: 10.1016/s1388-9842(01)00197-0. [PMID: 11812666]
  • T Tsutamoto, A Wada, K Maeda, T Hisanaga, D Fukai, Y Maeda, M Ohnishi, N Mabuchi, M Kinoshita. Digitalis increases brain natriuretic peptide in patients with severe congestive heart failure. American heart journal. 1997 Nov; 134(5 Pt 1):910-6. doi: 10.1016/s0002-8703(97)80014-2. [PMID: 9398103]
  • S R Goldsmith, A B Simon, E Miller. Effect of digitalis on norepinephrine kinetics in congestive heart failure. Journal of the American College of Cardiology. 1992 Oct; 20(4):858-63. doi: 10.1016/0735-1097(92)90185-p. [PMID: 1527296]
  • K Yoshimatsu, M Satake, K Shimomura, J I Sawada, T Terao. Determination of cardenolides in hairy root cultures of Digitalis lanata by enzyme-linked immunosorbent assay. Journal of natural products. 1990 Nov; 53(6):1498-502. doi: 10.1021/np50072a015. [PMID: 2089119]
  • M Klys, A Gross. Determination of deslanoside in antemortem and postmortem specimens. Unusual case report. Forensic science international. 1990 Apr; 45(3):231-8. doi: 10.1016/0379-0738(90)90179-3. [PMID: 2193860]
  • A Zarebska. [Histoenzymatic studies of the kidneys of albino rats after experimental administration of serpasil and deslanoside]. Patologia polska. 1985 Apr; 36(2):200-7. doi: NULL. [PMID: 3831873]
  • J E Doherty. Clinical use of digitalis glycosides. An update. Cardiology. 1985; 72(5-6):225-54. doi: 10.1159/000173883. [PMID: 2866838]
  • A Marzo, P Ghirardi, L Cavalca, R Alessio, G C Maggi, F Piscitello, M O Triulzi. Plasma turnover and excretion of deslanoside C-3H in man after parenteral administration. Il Farmaco; edizione pratica. 1981 Nov; 36(11):501-12. doi: NULL. [PMID: 7308424]
  • O M Bakke, A Aslaksen, V Lehmann, E Lien. Pharmacokinetics and serum concentration--effect relationship of intravenous deslanoside. Journal of cardiovascular pharmacology. 1981 Sep; 3(5):1015-25. doi: 10.1097/00005344-198109000-00012. [PMID: 6168847]
  • A Marzo, P Ghirardi, G C Maggi, A Tornaghi, F Di Roberto, G P Arisi. Plasma turnover and biliary and urinary excretion of deslanoside C-3H in man. Il Farmaco; edizione pratica. 1980 May; 35(5):265-9. doi: NULL. [PMID: 7449946]
  • C J Helke, K J Kellar, R A Gillis. Effect of in vivo deslanoside on the uptake of serotonin into platelets. Archives internationales de pharmacodynamie et de therapie. 1979 Nov; 242(1):44-9. doi: NULL. [PMID: 543748]
  • S M Fletcher, G Lawson, A C Moffat. Radioimmunoassay of cardiac glycosides in haemolysed blood: derivation of serum levels. Journal - Forensic Science Society. 1979 Jul; 19(3):183-8. doi: 10.1016/s0015-7368(79)71272-2. [PMID: 536730]
  • C J Helke, J D Souza, R A Gillis. Interaction of serotonin and deslanoside on cardiac rhythm in the cat. European journal of pharmacology. 1978 Sep; 51(2):167-77. doi: 10.1016/0014-2999(78)90341-2. [PMID: 699982]
  • A Marzo, P Ghirardi, B Brusoni, G Marchetti. Pharmacokinetics of deslanatoside C-3H administered parenterally to the guinea-pig, rabbit and dog. Archives internationales de pharmacodynamie et de therapie. 1978 May; 233(1):156-65. doi: NULL. [PMID: 686904]
  • J E Doherty, J J Kane. Digitalis glycosides--recent advances in clinical pharmacology and treatment. Southern medical journal. 1977 Apr; 70(4):470-6. doi: 10.1097/00007611-197704000-00032. [PMID: 850814]
  • L G Ekelund, G Johnsson, A Melcher, L Oro. Effects of cedilanid-D in combination with metoprolol on exercise tolerance and systolic time intervals in angina pectoris. The American journal of cardiology. 1976 Mar; 37(4):630-4. doi: 10.1016/0002-9149(76)90406-9. [PMID: 3961]
  • P Ghirardi, A Marzo. [Biliary and urinary elimination of desacetyl-lanatoside C in anesthetized guinea pigs]. Bollettino della Societa italiana di biologia sperimentale. 1974 Oct; 50(19):1610-1. doi: NULL. [PMID: 4458748]
  • F ANFOSSI, A GUARRAGGI. [Clinical observations on the use of a new digitalis preparation with rapid action: desacetyllanatoside C]. Minerva medica. 1963 Mar; 54(?):703-9. doi: ". [PMID: 14013116]
  • C D ENSELBERG, N DAVOODZADEH, H RIAHI. Intramuscular desacetyl lanatoside C: a safe and practical method of parenteral digitalization. New York state journal of medicine. 1958 Dec; 58(24):4011-8. doi: ". [PMID: 13613514]
  • I S ESKWITH, T F FOGARTY. The treatment of auricular arrhythmias with deslanoside. The American journal of cardiology. 1958 Nov; 2(5):579-85. doi: 10.1016/0002-9149(58)90185-1. [PMID: 13594846]
  • E HELLMAN, M PORT. Rapid digitalization of ambulatory patients with atrial fibrillation; use of intramuscularly given deslanoside followed by orally given acetyldigitoxin. Journal of the American Medical Association. 1958 May; 167(2):215-6. doi: 10.1001/jama.1958.72990190002015a. [PMID: 13538696]