O3125

Ouabain octahydrate

Name: Ouabain octahydrate
Brand: SIGMA

From plant seeds (Strophantus gratus), ≥95% (HPLC), steroid hormone, 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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All Photos(1)

About This Item

Empirical Formula (Hill Notation):

C₂₉H₄₄O₁₂ · 8H₂O

CAS Number:

11018-89-6

Molecular Weight:

728.77

NACRES:

NA.77

PubChem Substance ID:

24278610

UNSPSC Code:

12352200

EC Number:

211-139-3

MDL number:

MFCD00149240

Beilstein/REAXYS Number:

101712

Product Name

Ouabain octahydrate, ≥95% (HPLC), powder

InChI key

TYBARJRCFHUHSN-DMJRSANLSA-N

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

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

biological source

plant seeds (Strophantus gratus)

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

Quality Level

200

Gene Information

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

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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).

Disclaimer

Aqueous solutions can be autoclaved.

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.

General description

Ouabain is a steroid hormone, naturally present in mammals.

pictograms

GHS06,GHS08

signalword

Danger

hcodes

H300,H331,H373

pcodes

P260 - P264 - P271 - P301 + P310 - P304 + P340 + P311 - P314

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

WGK 3

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