Structure of Digitoxin

Digitoxin

Digitoksin

(3β,5β)-3-[(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide

Synonyms: Digoxin, Digitoxin, Digoksin, Dijitoksin

Chemical Class Cardiac Glycosides
Glycosides > Cardiac Glycosides
Molecular Formula C41H64O13
Molecular Weight 764.94 g/mol
Exact Mass 764.4355
CAS Number 71-63-6
SMILES
CC1C(C(C(O1)OC2C(C(C(O2)OC3C(C(C(O3)CO)O)O)O)O)O)OC4CCC5(C(C4)CCC6C5CCC7=CC(=O)OC7C6)O
InChI
InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
InChIKey
AZSRGORNWJXABF-AYOUDRJKSA-N
Lipinski's Rule of Five
765
MW (≤500)
2.6
LogP (≤5)
7
HBD (≤5)
13
HBA (≤10)
Additional Properties
5
Rotatable Bonds (≤10)
180.0
TPSA (Ų, ≤140)
2.0
pKa
Melting Point

250.0°C

Boiling Point

123.0°C

Density

2.0 g/cm³

Solubility
Water Solubility

Poorly soluble in water

Organic Solvent Solubility

Soluble in ethanol, chloroform, methanol

Optical Rotation

[α]D = 1.0°

Physical Description

White crystalline solid; bitter; odorless

fiziksel görünüş TR

UV-Vis Absorption (λmax)
223
IR Characteristic Bands

3400 – OH stretch 1735 – lactone carbonyl 1050–1150 – glycosidic C-O-C

MS Fragmentation Pattern

Aglycone (digitoxigenin) fragments Sequential sugar loss peaks

NMR Data

Typical signals for steroid nucleus + sugar protons

Pharmacological Activities
Cardiotonic
Pharmacological Notes

Inhibits Na⁺/K⁺-ATPase Increases intracellular Na⁺ → reduces Na⁺/Ca²⁺ exchange Raises intracellular Ca²⁺ → stronger cardiac contraction

farmakoloji TR

Clinical Notes

Historically used in heart failure and atrial fibrillation Narrow therapeutic index Risk of toxicity (nausea, arrhythmia, visual disturbances) Mostly replaced clinically by safer analogs, but still medically relevant

klinik not TR

External Databases
PubChem 439449 ChEMBL CHEMBL1431 ChEBI CHEBI:41879 DrugBank DB01396 KEGG C00690
Biosynthetic Pathways
  • Shikimate Pathway
    A seven-step pathway in plants and microorganisms leading to the biosynthesis of aromatic amino...
Structure Data Available
  • 2D Structure (MOL/SDF)
  • 3D Structure (PDB/MOL2)

Added: 2025-12-28

Updated: 2025-12-31