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Merck
CN

O2627

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
UNSPSC Code:
12352200
PubChem Substance ID:
24897964
MDL number:
MFCD00057697

Key Documents

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Product Name

Ouabagenin, ≥95%

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

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 key

BXSABLKMKAINIU-QOHCMMFCSA-N

assay

≥95%

storage temp.

2-8°C

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Biochem/physiol Actions

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

General description

The aglycone of the cardiac glycoside ouabain.

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
087H0592
044F0693

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H Núñez-Durán et al.
The American journal of physiology, 255(4 Pt 1), C479-C485 (1988-10-01)
Mammalian cells specifically internalize some molecular species through receptor-mediated endocytosis (RME). We have used four different experimental protocols to investigate whether ouabain enters cardiac cells of guinea pig atrium through this pathway. First, by electron microscope morphometry we found that
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
J F Templeton et al.
Journal of medicinal chemistry, 30(8), 1502-1505 (1987-08-01)
The synthesis of 14-hydroxy-14 beta-pregn-4-ene-3,20-dione (14 beta-hydroxyprogesterone) is described. This novel steroid is about 10 times more potent than progesterone and one-tenth as potent as ouabagenin in an [3H]ouabain radioligand binding assay and is the first in a series of
Total synthesis of ouabagenin and ouabain.
Hongxing Zhang et al.
Angewandte Chemie (International ed. in English), 47(7), 1272-1275 (2008-01-10)
T L Chan et al.
The Canadian journal of cardiology, 3(4), 197-204 (1987-05-01)
The mechanism of cardiac oscillatory activity induced by digitalis was studied in the canine ventricular muscle. We determined the role of sarcoplasmic reticulum in the phenomenon of oscillatory afterpotential and mechanical aftercontractions. Additionally we wished to study the interaction between
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