NAV

Digoxigenin

Identification

Generic Name
Digoxigenin
DrugBank Accession Number
DB03671
Background

Digoxigenin is a cardenolide which is the aglycon of digoxin. Can be obtained by hydrolysis of digoxin or from Digitalis orientalis L. and Digitalis lanata Ehrh.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 390.5131
Monoisotopic: 390.240624198
Chemical Formula
C23H34O5
Synonyms
  • Lanadigenin
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Pharmacology

Indication

Not Available

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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 / 12-hydroxysteroids / Butenolides / Tertiary alcohols / Enoate esters / Secondary alcohols / Lactones / Cyclic alcohols and derivatives / Polyols
show 5 more
Substituents
12-hydroxysteroid / 14-hydroxysteroid / 2-furanone / 3-beta-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative
show 17 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
3beta-hydroxy steroid, 3beta-sterol, 14beta-hydroxy steroid, 12beta-hydroxy steroid (CHEBI:42098) / Cardanolides and derivatives (LMST01120008)
Affected organisms
Not Available

Chemical Identifiers

UNII
NQ1SX9LNAU
CAS number
1672-46-4
InChI Key
SHIBSTMRCDJXLN-KCZCNTNESA-N
InChI
InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17-,18+,19-,21+,22+,23+/m1/s1
IUPAC Name
4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11R,11aS)-3a,7,11-trihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]-2,5-dihydrofuran-2-one
SMILES
[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)C1=CC(=O)OC1

References

General References
Not Available
PubChem Compound
15478
PubChem Substance
46509019
ChemSpider
14728
BindingDB
225707
ChEBI
42098
ChEMBL
CHEMBL1153
ZINC
ZINC000003982471
PDBe Ligand
DOG
Wikipedia
Digoxigenin
PDB Entries
1lke / 3ra7 / 4j8t / 4j9a / 5bvb

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 Solubility0.0632 mg/mLALOGPS
logP1.6ALOGPS
logP1.84Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.15Chemaxon
pKa (Strongest Basic)-1.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area86.99 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity105.16 m3·mol-1Chemaxon
Polarizability42.7 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9947
Blood Brain Barrier+0.6266
Caco-2 permeable-0.5482
P-glycoprotein substrateSubstrate0.7936
P-glycoprotein inhibitor INon-inhibitor0.881
P-glycoprotein inhibitor IINon-inhibitor0.8417
Renal organic cation transporterNon-inhibitor0.8028
CYP450 2C9 substrateNon-substrate0.8038
CYP450 2D6 substrateNon-substrate0.9018
CYP450 3A4 substrateSubstrate0.7262
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9099
CYP450 2D6 inhibitorNon-inhibitor0.9362
CYP450 2C19 inhibitorNon-inhibitor0.9256
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8702
Ames testNon AMES toxic0.8592
CarcinogenicityNon-carcinogens0.9629
BiodegradationNot ready biodegradable0.8827
Rat acute toxicity3.4699 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9704
hERG inhibition (predictor II)Inhibitor0.5085
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0btj-3931000000-dbf3a06930e85afcd289
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-004i-0009000000-306d8e9878a4c08a3e6b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0109000000-d029e288691f96cf1f52
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-05fr-0009000000-0bec63b86c9e78fb334f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-01ox-0129000000-e2a7f0f6ad129a0727aa
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0019000000-f8a8b596c19812693065
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0btj-3931000000-dbf3a06930e85afcd289
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-0019000000-424d1e25b26ecffb491e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-1d03d4319eb0747c600f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0abi-0039000000-6afe27dcc470b2fa30d4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000b-0009000000-743c903cb8286347abd7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ac9-0019000000-becab91d10f7ad310bc7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1934000000-83cd1c0b28f85a1af202
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-196.8065226
predicted
DarkChem Lite v0.1.0
[M-H]-204.4256226
predicted
DarkChem Lite v0.1.0
[M-H]-202.7424226
predicted
DarkChem Lite v0.1.0
[M-H]-181.55898
predicted
DeepCCS 1.0 (2019)
[M+H]+199.5620226
predicted
DarkChem Lite v0.1.0
[M+H]+207.6326226
predicted
DarkChem Lite v0.1.0
[M+H]+205.2486226
predicted
DarkChem Lite v0.1.0
[M+H]+183.38385
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.7579226
predicted
DarkChem Lite v0.1.0
[M+Na]+204.5716226
predicted
DarkChem Lite v0.1.0
[M+Na]+203.1797226
predicted
DarkChem Lite v0.1.0
[M+Na]+189.2958
predicted
DeepCCS 1.0 (2019)

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