DIGITONIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C56H92O29
Molecular Weight	1229.3123
Optical Activity	UNSPECIFIED
Defined Stereocenters	38 / 38
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12O[C@]3(CC[C@@H](C)CO3)[C@@H](C)[C@]1([H])[C@@]4(C)CC[C@@]5([H])[C@@]([H])(CC[C@@]6([H])C[C@@H](O[C@]7([H])O[C@H](CO)[C@H](O[C@]8([H])O[C@H](CO)[C@@H](O)[C@H](O[C@]9([H])OC[C@@H](O)[C@H](O)[C@H]9O)[C@H]8O[C@]%10([H])O[C@H](CO)[C@H](O)[C@H](O[C@]%11([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%11O)[C@H]%10O)[C@H](O)[C@H]7O)[C@H](O)C[C@]56C)[C@]4([H])[C@@H]2O

InChI

InChIKey=UVYVLBIGDKGWPX-KUAJCENISA-N

InChI=1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36-,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19870254 | https://www.ncbi.nlm.nih.gov/pubmed/417616 | https://www.ncbi.nlm.nih.gov/pubmed/23999162 | doi: 10.1093/ajcp/31.4.310

Digitonin is a steroidal saponin (saraponin) obtained from the foxglove plant Digitalis purpurea. As a non-ionic detergent Digitonin is commonly used to solubilize membrane-bound proteins. Digitonin forms a complex with its lipophilic terpenoid moiety with cholesterol in the biomembrane; additionally it binds to glycoproteins and glycolipids of the cell membrane with its sugar side chain. This leads to a severe tension of the biomembrane and influences membrane permeability. Digitonin, in combination with secondary metabolites, leads to a stronger inhibition of ABC transporters as when applied alone. Digitonin is used as a clinical reagent for the cholesterol determination. Digitonin mixed in the diet was well tolerated by rats and cynomolgus monkeys (Macaca fascicularis), and prevented the expected rise in plasma cholesterol in monkeys fed a diet containing butter and cholesterol.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23999162	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Hypercholesterolemia 47 Sources: https://www.ncbi.nlm.nih.gov/pubmed/417616	Preventing	Preclinical	Unknown Approved Use Unknown
Leukemia 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23999162	Primary	Basic research	Unknown Approved Use Unknown
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23999162	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
Copper-mediated cross-linking of S100A4, but not of S100A2, results in proinflammatory effects in melanoma cells.	2011 Sep 30	21924240

Patents

Sample Use Guides

In Vivo Use Guide

Macaca fascicularis: 0.4 g/100 g of food

Route of Administration: Oral

In Vitro Use Guide

The accumulation of Rho123 and CAM was assessed in Caco-2 and CEM/ADR5000 cells after treatment with the set of secondary metabolites in combination with 5 uM digitonin. The intracellular accumulation of Rho123 and CAM was significantly enhanced in Caco-2 cells in a dose dependent manner. The synergistic effect of EGCG, thymol, beta-sitosterol-O-glucoside, and harmine, in combination with digitonin, represent the highest enhancement factor (between 1.45 and 1.98) and inhibitory activity of P-gp efflux (between 220% and 469%).

Name

Type

Language

DIGITONIN

Common Name

English

NSC-23471

Code

English

DIGITONIN [MI]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID1025065