O3125

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

Properties

• 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.

Caution

Aqueous solutions can be autoclaved.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H300,H331,H373
• Precautionary Statements: P260 - P264 - P271 - P301 + P310 - P304 + P340 + P311 - P314
• Hazard Classifications: Acute Tox. 1 Oral - Acute Tox. 3 Inhalation - STOT RE 2
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3