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O3125

Sigma-Aldrich

Ouabain octahydrate

≥95% (HPLC), powder

Synonym(s):

1β,3β,5β,11α,14,19-Hexahydroxycard-20(22)-enolide 3-(6-deoxy-α-L-mannopyranoside), Acocantherine, G-Strophanthin

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About This Item

Empirical Formula (Hill Notation):
C29H44O12 · 8H2O
CAS Number:
11018-89-6
Molecular Weight:
728.77
Beilstein/REAXYS Number:
101712
EC Number:
211-139-3
MDL number:
MFCD00149240
UNSPSC Code:
12352200
PubChem Substance ID:
24278610
NACRES:
NA.77

biological source

plant seeds (Strophantus gratus)

Quality Level

200

assay

≥95% (HPLC)

form

powder

optical activity

[α]25/D −31 to −32.5° in H2O(lit.)

impurities

~8 mol/mol water

color

white

mp

260 °C

solubility

H2O: 10 mg/mL (cold)
ethanol: 10 mg/mL
H2O: 50 mg/mL (hot)

ε (extinction coefficient)

15.5 at 220 nm in H2O at 1 mM

storage temp.

room temp

SMILES string

O.O.O.O.O.O.O.O.C[C@@H]1O[C@@H](O[C@H]2C[C@@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)C6=CC(=O)OC6)[C@H](O)[C@H](O)[C@H]1O

InChI

1S/C29H44O12.8H2O/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;8*1H2/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-;;;;;;;;/m0......../s1

InChI key

TYBARJRCFHUHSN-DMJRSANLSA-N

Gene Information

human ... ATIC(471)
rat ... Atp1b1(25650)

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General description

Ouabain is a steroid hormone, naturally present in mammals.

Application

Ouabain octahydrate has been used:
  • to determine the effect of salt and ammonia in the external environment on the rate of activity of Na+ /K+ in either silver or golden perch
  • in the basolateral compartment to induce maximal baseline short-circuit current in rat fetal distal lung epithelial (FDLE) cells
  • as an Na+/K+ ATPase inhibitor to study the relation between blister formation and adenosine triphosphate (ATP) dependent maintenance of plasma membrane homeostasis

Biochem/physiol Actions

Cardiac glycoside, inhibits Na(+)/K(+) ATPase, regulates transcription of MDR (increase, Pgp) and MRP (increase MRP1 and decrease CFTR, cyctic fibrosis transport receptor or cAMP-activated Cl- channel) genes, also alters localization of MRP1. Ouabain resistance is associated with appearance of Na(+)/K(+) ATPase isoforms with low binding affinity.
Ouabain has its specific binding site on integral proteins of the plasma membrane. Heart disease is treated using ouabain derivatives. Increased ouabain production is observed during exercise in humans. Abnormally high levels of ouabain are indicated in congestive heart failure and hypertension. Ouabain signalling affects intracellular calcium levels, which is known to activate nuclear factor κB (NFκB).

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Caution

Aqueous solutions can be autoclaved.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 1 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The present study aimed to investigate the effects of berberine (BRB) on spatial and learning memory, anxiety, acetylcholinesterase activity and cell death in an experimental model of intracerebroventricular streptozotocin (ICV-STZ) induced sporadic Alzheimer's-like dementia. Sixty male Wistar rats were randomly
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