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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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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
M B Pamnani et al.
Hypertension (Dallas, Tex. : 1979), 18(3), 316-324 (1991-09-11)
Reports from several laboratories suggest the presence of an ouabainlike compound in plasma and various animal tissues, particularly during acute volume expansion and in low-renin hypertension. It has been hypothesized that this compound, through inhibition of the Na(+)-K+ pump, can
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
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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