ChemFOnt: Showing chemical card for Digitoxin (CFc000009738)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:58 UTC

Chemfont ID

CFc000009738

Molecule Identification

Common Name

Digitoxin

Definition

Digitoxin is a cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain. It has a role as an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It derives from a digitoxigenin. It is a conjugate acid of a digitoxin(1-). Digitoxin appears as odorless white or pale buff microcrystalline powder. It is a cardiac glycoside sometimes used in place of digoxin. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. Digitoxin inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Digitoxin also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Crystodigin	ChEBI
Digitoxoside	ChEBI
Digitoksin	HMDB
Digitoxinum	HMDB
Bürger, digitoxin	HMDB
Didier, digitoxin	HMDB
Digitoxin awd	HMDB
Digitoxin didier	HMDB
Digimed	HMDB
Digophton	HMDB
Nativelle, digitaline	HMDB
Digimerck	HMDB
Digitoxin bürger	HMDB
AWD, digitoxin	HMDB
Coramedan	HMDB
Digitaline nativelle	HMDB
Digitoxin philo	HMDB
Digitoxin-philo	HMDB

Chemical Formula

C₄₁H₆₄O₁₃

Average Molecular Weight

764.9391

Monoisotopic Molecular Weight

764.434692134

IUPAC Name

4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

Traditional Name

CAS Registry Number

71-63-6

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](C2)O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]3C[C@H](O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1

InChI Identifier

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

InChI Key

WDJUZGPOPHTGOT-XUDUSOBPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroidal glycoside
Oligosaccharide
14-hydroxysteroid
Hydroxysteroid
Glycosyl compound
O-glycosyl compound
2-furanone
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cardenolide glycoside (CHEBI:28544 )
cardanolide (C06955 )
Cardanolides and derivatives (C06955 )
Cardanolide and derivatives (C06955 )
Cardiac glycosides (C06955 )
Cardanolides and derivatives (LMST01120018 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0015468)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0015468)

Source

Exogenous

Exogenous (HMDB: HMDB0015468)

Food

Food (HMDB: HMDB0015468)

Pulse

Bean

Common bean (FooDB: FOOD00134)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0015468)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0015468)

Lipid metabolism pathway (HMDB: HMDB0015468)

Cellular process

Cell signaling (HMDB: HMDB0015468)

Biochemical process

Lipid transport (HMDB: HMDB0015468)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	2.33	ALOGPS
logP	3.6	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	191.72 m³·mol⁻¹	ChemAxon
Polarizability	83.54 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon