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
[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
Molecular Formula | C56H92O29 |
Molecular Weight | 1229.3123 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 36 / 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 |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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
by
admin
on
Edited
Fri Dec 15 15:50:10 GMT 2023
by
admin
on
Fri Dec 15 15:50:10 GMT 2023
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Record UNII |
KOO5CM684H
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Record Status |
Validated (UNII)
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Record Version |
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DTXSID1025065
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100000127482
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DIGITONIN
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Related Record | Type | Details | ||
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ACTIVE MOIETY |