O3125

Ouabain octahydrate

≥95% (HPLC), powder

• Synonyme(s) : 1β,3β,5β,11α,14,19-Hexahydroxycard-20(22)-enolide 3-(6-deoxy-α-L-mannopyranoside), Acocantherine, G-Strophanthin
• Formule empirique (notation de Hill): C₂₉H₄₄O₁₂ · 8H₂O
• Numéro CAS: 11018-89-6
• Poids moléculaire : 728.77
• Numéro Beilstein : 101712
• Numéro CE : 211-139-3
• Numéro MDL: MFCD00149240
• Code UNSPSC : 12352200
• ID de substance PubChem : 24278610
• Nomenclature NACRES : NA.77

Propriétés

• Source biologique: plant seeds (Strophantus gratus)
• Pureté: ≥95% (HPLC)
• Forme: powder
• Activité optique: [α]25/D −31 to −32.5° in H₂O(lit.)
• Impuretés: ~8 mol/mol water
• Couleur: white
• Pf: 260 °C
• Solubilité: H₂O: 10 mg/mL (cold); ethanol: 10 mg/mL; H₂O: 50 mg/mL (hot)
• ε (coefficient d'extinction): 15.5 at 220 nm in H₂O at 1 mM
• Température de stockage: room temp
• Chaîne SMILES: 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
• Clé InChI: TYBARJRCFHUHSN-DMJRSANLSA-N
• Informations sur le gène: human ... ATIC(471) ; rat ... Atp1b1(25650)

Description

Description générale

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

Actions biochimiques/physiologiques

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).

Caractéristiques et avantages

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.

Attention

Aqueous solutions can be autoclaved.

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08
• Mention d'avertissement: Danger
• Mentions de danger: H300,H331,H373
• Conseils de prudence: P260 - P264 - P271 - P301 + P310 - P304 + P340 + P311 - P314
• Classification des risques: Acute Tox. 1 Oral - Acute Tox. 3 Inhalation - STOT RE 2
• Code de la classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3