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O3125 Sigma-Aldrich

Ouabain octahydrate

≥95% (HPLC), powder

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

  • CAS Number 11018-89-6

  • Empirical Formula (Hill Notation) C29H44O12 · 8H2O

  • Molecular Weight 728.77

  •  Beilstein/REAXYS Number 101712

  •  EC Number 211-139-3

  •  MDL number MFCD00149240

  •  PubChem Substance ID 24278610

  •  NACRES NA.77

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Properties

Related Categories A to C, Adenosinetriphosphatase, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
Quality Level   200
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
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)

Description

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.

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Caution

Aqueous solutions can be autoclaved.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 1544PSN1 6.1 / PGI
WGK Germany 
WGK 3
Protocols & Articles

Articles

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Peer-Reviewed Papers
15

References

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