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Substance Name: Digitonin
RN: 11024-24-1
UNII: KOO5CM684H
InChIKey: UVYVLBIGDKGWPX-KUAJCENISA-N

Note

  • A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.

Molecular Formula

  • C56-H92-O29

Molecular Weight

  • 1229.3138
 

Classification Codes

  • Indicators and Reagents
  • Mutation Data
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Names and Synonyms

Name of Substance

  • Digitonin

MeSH Heading

  • Digitonin

Synonyms

  • 5-19-03-00603 (Beilstein Handbook Reference)
  • AI3-44893
  • BRN 0078654
  • Digitin
  • Digitogenin, glycoside
  • Digitonin
  • Digitonine
  • EINECS 234-255-6
  • NSC 23471
  • UNII-KOO5CM684H

Systematic Names

  • beta-D-Galactopyranoside, (2alpha,3beta,5alpha,15beta,25R)-2,15-dihydroxyspirostan-3-yl O-beta-D-glucopyranosyl-(1-3)-O-beta-D-galactopyranosyl-(1-2)-O-(beta-D-xylopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-
  • beta-D-Galactopyranoside, (2alpha,3beta,5alpha,15beta,25R)-2,15-dihydroxyspirostan-3-yl O-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->2)-O-(beta-D-xylopyranosyl-(1->3))-O-beta-D-glucopyranosyl-(1->4)-
  • beta-D-Galactopyranoside, (2alpha,3beta,5alpha,15beta,25R)-2,15-dihydroxyspirostan-3-yl O-beta-D-glucopyranosyl-(1.fwdarw.3)-O-beta-D-galactopyranosyl-(1.fwdarw.2)-O-(beta-D-xylopyranosyl-(1.fwdarw.3))-O-beta-D-glucopyranosyl-(1.fwdarw.4)-
  • Digitonin

Registry Numbers

CAS Registry Number

  • 11024-24-1

FDA UNII

  • KOO5CM684H

Other Registry Numbers

  • 35-62-1
  • 52781-76-7

System Generated Number

  • 0011024241

Structure Descriptors

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

InChIKey

UVYVLBIGDKGWPX-KUAJCENISA-N

Smiles

C[C@@H]1CC[C@@]2(OC1)O[C@H]3[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@]4(C)[C@H]3[C@@H]2C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD10 intraperitoneal 20mg/kg (20mg/kg)   Pharmaceutical Chemistry Journal Vol. 11, Pg. 749, 1977.
mouse LDLo intravenous 10mg/kg (10mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
mouse LDLo oral 90mg/kg (90mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
mouse LDLo subcutaneous 200mg/kg (200mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD50 intravenous 4mg/kg (4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 815, 1962.
rat LD50 oral > 50mg/kg (50mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 815, 1962.