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630-60-4 分子结构
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4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

ChemBase编号:963
分子式:C29H44O12
平均质量:584.65246
单一同位素质量:584.28327685
SMILES和InChIs

SMILES:
O[C@@]12[C@H]3[C@@H]([C@@]4([C@](O)(CC3)C[C@@H](O[C@@H]3O[C@H]([C@H](O)[C@@H](O)[C@H]3O)C)C[C@H]4O)CO)[C@H](O)C[C@@]1([C@H](CC2)C1=CC(=O)OC1)C
Canonical SMILES:
OC[C@@]12[C@H](O)C[C@@H](C[C@@]2(O)CC[C@@H]2[C@@H]1[C@H](O)C[C@]1([C@]2(O)CC[C@@H]1C1=CC(=O)OC1)C)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI:
InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
InChIKey:
LPMXVESGRSUGHW-HBYQJFLCSA-N

引用这个纪录

CBID:963 http://www.chembase.cn/molecule-963.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one
4-[(1S,2R,3R,5S,7S,10R,11S,14R,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2,5-dihydrofuran-2-one
IUPAC传统名
ouabain
商标名
Acocantherin
Astrobain
G-Strophicor
Gratibain
Gratus Strophanthin
Kombetin
Purostrophan
Rectobaina
Solufantina
Strodival
Strophalen
Strophoperm
Strophosan
Uabaina
Uabanin
别名
Ouabain Octahydrate
Ouabain, Octahydrate
Ouabaine
G-Strophanthin
Ouabagenin L-Rhamnoside
Strophanthin G
Strophanthin-G
Ouabain
CAS号
630-60-4
PubChem SID
160964426
46505479
PubChem CID
439501
CHEBI ID
472805
ATC码
C01AC01
CHEMBL
447086
Chemspider ID
388599
DrugBank ID
DB01092
KEGG ID
D00112
美国药典/FDA物质标识码
5ACL011P69
维基百科标题
Ouabain

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格
MP Biomedicals
05218018 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 7.181447  质子受体 11 
质子供体 LogD (pH = 5.5) -2.7907462 
LogD (pH = 7.4) -3.204898  Log P -2.781806 
摩尔折射率 140.8338 cm3 极化性 56.89489 Å3
极化表面积 206.6 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P -1.03  LOG S -2.1 
溶解度 4.61e+00 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
1.03E+004 mg/L expand 查看数据来源
疏水性(logP)
-1.2 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
质检报告
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详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia
MP Biomedicals -  05218018 external link
MP Biomedicals Rare Chemical collection
DrugBank -  DB01092 external link
Item Information
Drug Groups approved
Description A cardioactive glycoside consisting of rhamnose and ouabagenin, obtained from the seeds of Strophanthus gratus and other plants of the Apocynaceae; used like digitalis. It is commonly used in cell biological studies as an inhibitor of the NA(+)-K(+)-exchanging ATPase. [PubChem]
Indication For the treatment of atrial fibrillation and flutter and heart failure
Pharmacology Ouabain, a cardiac glycoside similar to digitoxin, is 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.
Affected Organisms
Humans and other mammals
Protein Binding 60%
References
Gao J, Wymore RS, Wang Y, Gaudette GR, Krukenkamp IB, Cohen IS, Mathias RT: Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides. J Gen Physiol. 2002 Apr;119(4):297-312. [Pubmed]
Saunders R, Scheiner-Bobis G: Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump. Eur J Biochem. 2004 Mar;271(5):1054-62. [Pubmed]
Hamlyn JM, Blaustein MP, Bova S, DuCharme DW, Harris DW, Mandel F, Mathews WR, Ludens JH: Identification and characterization of a ouabain-like compound from human plasma. Proc Natl Acad Sci U S A. 1991 Jul 15;88(14):6259-63. [Pubmed]
Hamlyn JM, Laredo J, Shah JR, Lu ZR, Hamilton BP: 11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications. Ann N Y Acad Sci. 2003 Apr;986:685-93. [Pubmed]
Laredo J, Hamilton BP, Hamlyn JM: Ouabain is secreted by bovine adrenocortical cells. Endocrinology. 1994 Aug;135(2):794-7. [Pubmed]
External Links
Wikipedia

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Gao J, Wymore RS, Wang Y, Gaudette GR, Krukenkamp IB, Cohen IS, Mathias RT: Isoform-specific stimulation of cardiac Na/K pumps by nanomolar concentrations of glycosides. J Gen Physiol. 2002 Apr;119(4):297-312. Pubmed
  • Saunders R, Scheiner-Bobis G: Ouabain stimulates endothelin release and expression in human endothelial cells without inhibiting the sodium pump. Eur J Biochem. 2004 Mar;271(5):1054-62. Pubmed
  • Hamlyn JM, Blaustein MP, Bova S, DuCharme DW, Harris DW, Mandel F, Mathews WR, Ludens JH: Identification and characterization of a ouabain-like compound from human plasma. Proc Natl Acad Sci U S A. 1991 Jul 15;88(14):6259-63. Pubmed
  • Hamlyn JM, Laredo J, Shah JR, Lu ZR, Hamilton BP: 11-hydroxylation in the biosynthesis of endogenous ouabain: multiple implications. Ann N Y Acad Sci. 2003 Apr;986:685-93. Pubmed
  • Laredo J, Hamilton BP, Hamlyn JM: Ouabain is secreted by bovine adrenocortical cells. Endocrinology. 1994 Aug;135(2):794-7. Pubmed
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专利

专利

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