IMPPAT Phytochemical information: 
Digitoxin
Digitoxin
Summary

SMILES: O=C1OCC(=C1)[C@H]1CC[C@]2([C@]1(C)CC[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@@H](C2)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O[C@H]1C[C@H](O)[C@@H]([C@H](O1)C)O)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: WDJUZGPOPHTGOT-XUDUSOBPSA-N
DeepSMILES: O=COCC=C5)[C@H]CC[C@][C@]5C)CC[C@H][C@H]6CC[C@H][C@]6C)CC[C@@H]C6)O[C@H]C[C@H]O)[C@@H][C@H]O6)C))O[C@H]C[C@H]O)[C@@H][C@H]O6)C))O[C@H]C[C@H]O)[C@@H][C@H]O6)C))O))))))))))))))))))))))))))))O
Scaffold Graph/Node/Bond level: O=C1C=C(C2CCC3C2CCC2C4CCC(OC5CCC(OC6CCC(OC7CCCCO7)CO6)CO5)CC4CCC23)CO1
Scaffold Graph/Node level: OC1CC(C2CCC3C2CCC2C4CCC(OC5CCC(OC6CCC(OC7CCCCO7)CO6)CO5)CC4CCC23)CO1
Scaffold Graph level: CC1CCC(C2CCC3C2CCC2C4CCC(CC5CCC(CC6CCC(CC7CCCCC7)CC6)CC5)CC4CCC23)C1
Functional groups: CC1=CC(=O)OC1; CO; C[C@H](OC)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Cardenolides
Synonymous chemical names:
digitoxin, digitoxin,ban,inn,usan
External chemical identifiers:
CID:441207; ChEMBL:CHEMBL254219; ChEBI:28544; ZINC:ZINC000095862733; FDASRS:E90NZP2L9U; SureChEMBL:SCHEMBL20940; MolPort-001-742-606
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Digitoxin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 764.95
Log P RDKit 3.25
Topological polar surface area (Å2) RDKit 182.83
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 41
Number of heavy atoms RDKit 54
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 20
Stereochemical complexity RDKit 0.49
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 38
Shape complexity RDKit 0.93
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
Digitoxin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.1885
Digitoxin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.65
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Digitoxin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000216797NFKBIA700
ENSP00000239938EGR1800
ENSP00000287647FANCD2800
ENSP00000295598ATP1A1918
ENSP00000295897ALB926
ENSP00000297494NOS3726
ENSP00000306512IL8750
ENSP00000330237CASP9700
ENSP00000351273CASP8700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.