1183-35-3

Basic information

• Product Name: DIHYDROOUABAIN
• Synonyms: DIHYDRO-G-STROPHANTHIN;DIHYDROOUABAIN;,11-alpha,14,19-pentahydroxy-;5-beta-20-xi-cardanolide,3-beta-((6-deoxy-alpha-l-mannopyranosyl)oxy)-1-beta,5;dihydro-g-strophathin;dihydroouabin;(20xi)-3beta-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-1beta,5beta,11alpha,14,19-pentahydroxycardanolide;DIHYDROOUABAIN(RG)
• CAS NO: 1183-35-3
• Molecular Formula: C₂₉H₄₆O₁₂
• Molecular Weight: 586.67
• EINECS: 214-663-0
• Product Categories: Cardioglycosides & Glycosides;Ion Pump InhibitorsMonovalent Ion Channels;Monovalent Ion Channels;Other Sodium Channel Modulators;Sodium Channel Modulators;Voltage-gated Ion Channels
• Mol File: 1183-35-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 168-170 °C
• Boiling Point: 827.7 °C at 760 mmHg
• Flash Point: 268.5 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.641
• PKA: 13.04±0.70(Predicted)
• CAS DataBase Reference: DIHYDROOUABAIN(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDROOUABAIN(1183-35-3)
• EPA Substance Registry System: DIHYDROOUABAIN(1183-35-3)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45
• RIDADR: 1544
• WGK Germany: 3
• RTECS: FH4551000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 1183-35-3(Hazardous Substances Data)

Usage

Uses

Dihydroouabain is a cardiac glycoside, a natural product found to be effective against various cancer cells. An inotropic drug and an inhibitor of sodium-potassium pump.

InChI:InChI=1/C29H46O12/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/h13-19,21-25,30-32,34-38H,3-12H2,1-2H3/t13-,14?,15-,16+,17?,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1

Upstream product

• 630-60-4 ouabain 

Relevant articles and documents

Cardiac glycoside activities link Na+/K+ ATPase ion-transport to breast cancer cell migration via correlative SAR

The cardiac glycosides ouabain and digitoxin, established Na+/K+ ATPase inhibitors, were found to inhibit MDA-MB-231 breast cancer cell migration through an unbiased chemical genetics screen for cell motility. The Na+/K+ ATPase acts both as an ion-transporter and as a receptor for cardiac glycosides. To delineate which function is related to breast cancer cell migration, structure-activity relationship (SAR) profiles of cardiac glycosides were established at the cellular (cell migration inhibition), molecular (Na+/K+ ATPase inhibition), and atomic (computational docking) levels. The SAR of cardiac glycosides and their analogs revealed a similar profile, a decrease in potency when the parent cardiac glycoside structure was modified, for each activity investigated. Since assays were done at the cellular, molecular, and atomic levels, correlation of SAR profiles across these multiple assays established links between cellular activity and specific protein-small molecule interactions. The observed antimigratory effects in breast cancer cells are directly related to the inhibition of Na+/K+ transport. Specifically, the orientation of cardiac glycosides at the putative cation permeation path formed by transmembrane helices αM1-M6 correlates with the Na+ pump activity and cell migration. Other Na+/K+ ATPase inhibitors that are structurally distinct from cardiac glycosides also exhibit antimigratory activity, corroborating the conclusion that the antiport function of Na+/K+ ATPase and not the receptor function is important for supporting the motility of MDA-MB-231 breast cancer cells. Correlative SAR can establish new relationships between specific biochemical functions and higher-level cellular processes, particularly for proteins with multiple functions and small molecules with unknown or various modes of action.