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Merck

O3125

Ouabain octahydrate

From plant seeds (Strophantus gratus), ≥95% (HPLC), steroid hormone, powder

Sinónimos:

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

Fórmula empírica (notación de Hill):
C29H44O12 · 8H2O
Número CAS:
11018-89-6
Peso molecular:
728.77
NACRES:
NA.77
PubChem Substance ID:
24278610
UNSPSC Code:
12352200
EC Number:
211-139-3
MDL number:
MFCD00149240
Beilstein/REAXYS Number:
101712

Nombre del producto

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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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

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 3 Inhalation - STOT RE 2

Clase de almacenamiento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

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Certificados de análisis (COA)

Lot/Batch Number
BCCP0141
BCCN3412
BCCM1642
BCCJ7417
BCCH8909

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Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

Depletion of the central metabolite NAD leads to oncosis mediated cell death
Del Nagro CX, et al.
The Journal of biological chemistry, jbc-M114 (2014)
Maria A Lim et al.
Frontiers in pharmacology, 8, 818-818 (2017-12-01)
Despite a broad spectrum of anti-arthritic drugs currently on the market, there is a constant demand to develop improved therapeutic agents. Efficient compound screening and rapid evaluation of treatment efficacy in animal models of rheumatoid arthritis (RA) can accelerate the
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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