Identification

Generic Name
Digitoxigenin
DrugBank Accession Number
DB04177
Background

Digitoxigenin is a cardenolide which is the aglycon of digitoxin.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 374.5137
Monoisotopic: 374.245709576
Chemical Formula
C23H34O4
Synonyms
  • Cerberigenin
  • Echujetin
  • Evonogenin
  • Thevetigenin
External IDs
  • NSC-407806

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid lactones
Direct Parent
Cardenolides and derivatives
Alternative Parents
3-beta-hydroxysteroids / 14-hydroxysteroids / Butenolides / Tertiary alcohols / Enoate esters / Secondary alcohols / Lactones / Cyclic alcohols and derivatives / Oxacyclic compounds / Monocarboxylic acids and derivatives
show 3 more
Substituents
14-hydroxysteroid / 2-furanone / 3-beta-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 15 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
3beta-hydroxy steroid, 14beta-hydroxy steroid (CHEBI:42219) / Cardanolides and derivatives (LMST01120001)
Affected organisms
Not Available

Chemical Identifiers

UNII
S63WOD4VOL
CAS number
143-62-4
InChI Key
XZTUSOXSLKTKJQ-CESUGQOBSA-N
InChI
InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1
IUPAC Name
4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one
SMILES
[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@H](CC[C@]34O)C3=CC(=O)OC3)[C@@]1(C)CC[C@H](O)C2

References

General References
Not Available
PubChem Compound
4369270
PubChem Substance
46508220
ChemSpider
3571902
BindingDB
66977
ChEBI
42219
ChEMBL
CHEMBL1453
ZINC
ZINC000003875959
PDBe Ligand
DTX
Wikipedia
Digitoxigenin
PDB Entries
1lnm / 7w11 / 7w1b

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0244 mg/mLALOGPS
logP2.72ALOGPS
logP3.07ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)0.25ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity103.64 m3·mol-1ChemAxon
Polarizability42.57 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.6906
Caco-2 permeable+0.6344
P-glycoprotein substrateSubstrate0.7862
P-glycoprotein inhibitor INon-inhibitor0.8372
P-glycoprotein inhibitor IINon-inhibitor0.7479
Renal organic cation transporterNon-inhibitor0.7858
CYP450 2C9 substrateNon-substrate0.8069
CYP450 2D6 substrateNon-substrate0.9067
CYP450 3A4 substrateSubstrate0.7478
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9355
CYP450 2D6 inhibitorNon-inhibitor0.9253
CYP450 2C19 inhibitorNon-inhibitor0.9237
CYP450 3A4 inhibitorNon-inhibitor0.6717
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.8839
CarcinogenicityNon-carcinogens0.9627
BiodegradationNot ready biodegradable0.8906
Rat acute toxicity2.9314 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9699
hERG inhibition (predictor II)Inhibitor0.5355
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a59-2941000000-3faff0ef96c1702ba849

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52