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O3125

Sigma-Aldrich

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

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About This Item

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

Source biologique

plant seeds (Strophantus gratus)

Niveau de qualité

200

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)

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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.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H300,H331,H373

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Male sex is associated with a reduced alveolar epithelial sodium transport
Kaltofen T, et al.
PLoS ONE, 10(8), e0136178-e0136178 (2015)
M Juhaszova et al.
Proceedings of the National Academy of Sciences of the United States of America, 94(5), 1800-1805 (1997-03-04)
Three isoforms (alpha1, alpha2, and alpha3) of the catalytic (alpha) subunit of the plasma membrane (PM) Na+ pump have been identified in the tissues of birds and mammals. These isoforms differ in their affinities for ions and for the Na+
Narakorn Khunweeraphong et al.
Scientific reports, 7(1), 13767-13767 (2017-10-25)
The human ABC transporter ABCG2 (Breast Cancer Resistance Protein, BCRP) is implicated in anticancer resistance, in detoxification across barriers and linked to gout. Here, we generate a novel atomic model of ABCG2 using the crystal structure of ABCG5/G8. Extensive mutagenesis
Juliana Sorraila de Oliveira et al.
Neurotoxicology, 57, 241-250 (2016-11-05)
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
Gill ATPase activities of silver perch, Bidyanus bidyanus (Mitchell), and golden perch, Macquaria ambigua (Richardson): effects of environmental salt and ammonia
Alam Mostafa and Frankel Theresa L
Aquaculture (Amsterdam, Netherlands), 251(1), 118-133 (2006)
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