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O2627

Sigma-Aldrich

Ouabagenin

≥95%

Synonym(s):

1β,3β,5,11α,14,19-Hexahydroxy-5β-card-20(22)-enolide, G-Strophanthidin

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About This Item

Empirical Formula (Hill Notation):
C23H34O8
CAS Number:
508-52-1
Molecular Weight:
438.51
MDL number:
MFCD00057697
UNSPSC Code:
12352200
PubChem Substance ID:
24897964

assay

≥95%

storage temp.

2-8°C

SMILES string

[H][C@@]12CC[C@]3(O)C[C@@H](O)C[C@@H](O)[C@]3(CO)[C@@]1([H])[C@H](O)C[C@]4(C)[C@H](CC[C@]24O)C5=CC(=O)OC5

InChI

1S/C23H34O8/c1-20-9-16(26)19-15(23(20,30)5-3-14(20)12-6-18(28)31-10-12)2-4-21(29)8-13(25)7-17(27)22(19,21)11-24/h6,13-17,19,24-27,29-30H,2-5,7-11H2,1H3/t13-,14+,15+,16+,17+,19+,20+,21-,22+,23-/m0/s1

InChI key

BXSABLKMKAINIU-QOHCMMFCSA-N

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General description

The aglycone of the cardiac glycoside ouabain.

Biochem/physiol Actions

Ouabagenin exerts cardiotonic effects through inhibition of Na+/K+-ATPase like the glycosides, albeit at significantly lower potency.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Inhalation - STOT RE 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
087H0592
044F0693

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M Chatterjee et al.
Steroids, 60(6), 477-483 (1995-06-01)
Ouabain shows high binding ability to myocardial Na+,K(+)-ATPase and, therefore, a suitably radiolabeled derivative of this compound may find use in myocardial imaging. In this pilot experiment we report the preparation of several chloroacetylated and iodoacetylated ouabagenins. These intermediates may
D Bose et al.
Canadian journal of physiology and pharmacology, 66(9), 1232-1238 (1988-09-01)
Scattered light intensity fluctuation (SLIF) of coherent light by a strip of ventricular muscle during diastole is believed to be due to asynchronous cellular motion within the myocyte as a result of spontaneous release of Ca from the sacoplamic reticulum.
Total synthesis of ouabagenin and ouabain.
Hongxing Zhang et al.
Angewandte Chemie (International ed. in English), 47(7), 1272-1275 (2008-01-10)
J G Dong et al.
Enantiomer, 2(5), 397-409 (1997-01-01)
Ample experimental evidence shows that the principle of pairwise additivity holds in exciton coupled CD systems consisting of three or more interacting chromophores. This principle is one of the most important from a practical viewpoint. However, the rule has so
V A Penniyaynen et al.
Bulletin of experimental biology and medicine, 154(4), 419-420 (2013-03-15)
Organotypic culture was used to study the effects of glycoside ouabain and its aglycone ouaba-genin on the growth of skin explants from 10-12-day chicken embryos. The tested agents demonstrated dose-dependent inhibition of skin growth. The effective concentrations imply that ouabain
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