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
SMILES
C[C@H]1[C@H]2[C@@H](O[C@]13CC[C@@H](C)CO3)[C@@H](O)[C@H]4[C@@H]5CC[C@H]6C[C@@H](O[C@@H]7O[C@H](CO)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O[C@@H]9OC[C@@H](O)[C@H](O)[C@H]9O)[C@H]8O[C@@H]%10O[C@H](CO)[C@H](O)[C@H](O[C@@H]%11O[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@]6(C)[C@H]5CC[C@]24C
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
| Molecular Formula | C56H92O29 |
| Molecular Weight | 1229.3123 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 38 / 38 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|---|
Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23999162 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Copper-mediated cross-linking of S100A4, but not of S100A2, results in proinflammatory effects in melanoma cells. | 2011-09-30 |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
|
| Discovery of novel antifungal (1,3)-beta-D-glucan synthase inhibitors. | 2000-02 |
|
| Screening for new compounds with antiherpes activity. | 1984-10 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/417616
Macaca fascicularis: 0.4 g/100 g of food
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23999162
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%).
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 18:10:24 GMT 2025
by
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Mon Mar 31 18:10:24 GMT 2025
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KOO5CM684H
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Validated (UNII)
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DIGITONIN
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