U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DIGITONIN

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Macaca fascicularis: 0.4 g/100 g of food
Route of Administration: Oral
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 Fri Dec 15 15:50:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:50:10 GMT 2023
Record UNII
KOO5CM684H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIGITONIN
MI  
Common Name English
NSC-23471
Code English
DIGITONIN [MI]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID1025065
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
SMS_ID
100000127482
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
WIKIPEDIA
DIGITONIN
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
234-255-6
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
MERCK INDEX
m4450
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY Merck Index
CHEBI
27729
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
MESH
D004072
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
CAS
11024-24-1
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
NSC
23471
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
PUBCHEM
6474107
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
EVMPD
SUB33508
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
FDA UNII
KOO5CM684H
Created by admin on Fri Dec 15 15:50:10 GMT 2023 , Edited by admin on Fri Dec 15 15:50:10 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY