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Digoxin

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Identification
Molecular formula
C41H64O14
CAS number
20830-75-5
IUPAC name
(2R,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-methyl-tetrahydropyran-3,4,5-triol
State
State

At room temperature, digoxin exists as a solid compound.

Melting point (Celsius)
249.00
Melting point (Kelvin)
522.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
780.94g/mol
Molar mass
780.9420g/mol
Density
1.2800g/cm3
Appearence

Digoxin appears as a white or almost white crystalline powder. It is practically odorless and has a bitter taste.

Comment on solubility

Solubility of the Compound

The solubility of the compound (2R,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[[1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-methyl-tetrahydropyran-3,4,5-triol can be characterized by several significant features:

  • Polarity: Due to the presence of multiple hydroxyl (-OH) groups, this compound is likely to exhibit a high degree of polarity, enhancing its ability to dissolve in polar solvents such as water.
  • Hydrogen Bonding: The compound's structure promotes extensive hydrogen bonding, which can further facilitate its solubility in aqueous environments.
  • Hydroxymethyl Groups: The presence of hydroxymethyl groups can provide additional solubility in various solvents, potentially expanding its miscibility range.

However, due to the complex nature of its structure, actual solubility data may vary:

  • In Water: Given the numerous hydrophilic sites, the compound is expected to be soluble or at least partially soluble in water.
  • In Organic Solvents: Solubility in non-polar organic solvents may be limited due to its complex polar functionalities.

In summary, the solubility characteristics of this compound are influenced by its heavy reliance on hydrogen bonding, polar functional groups, and structural intricacies, making it a fascinating study subject in the realm of chemistry.

Interesting facts

Interesting Facts about the Compound

This compound, a complex polyol, has garnered attention in the fields of biochemistry and pharmacology due to its intricate structure and potential biological activities.

Structural Complexity

Some fascinating aspects of its structure include:

  • Multiple Hydroxyl Groups: The presence of numerous hydroxyl (–OH) groups contributes to its solubility and reactivity, making it a versatile compound in various chemical reactions.
  • Stereoisomerism: With multiple chiral centers, this compound can exist in various stereoisomeric forms. Understanding the implications of stereochemistry is crucial, as it can affect biological interactions.
  • Cycloalkane Framework: The complex bicyclic and tetracyclic components may influence the compound’s stability and reactivity in biochemical pathways.

Potential Biological Applications

Research into similar structures has indicated several intriguing possibilities:

  • Antioxidant Properties: Compounds that share structural features with this one have been investigated for their ability to neutralize free radicals.
  • Therapeutic Potential: Due to its structural similarities to known biologically active compounds, it may serve as a candidate for drug development targeting diseases like cancer or diabetes.
  • Natural Sourcing: Many such compounds are derived from natural sources, which raises exciting prospects for sustainable drug design.

Quote

As one renowned chemist stated, "The complexity of natural compounds often reflects their functionality in biological systems." This compound is a prime example of how structure informs function, offering insights into new therapeutic approaches.

In summary, the study of this compound not only reveals the fascinating world of complex organic chemistry but also opens doors to potential innovations in medicine and biochemistry.

Synonyms
Solatunine
SOLANINE
alpha-Solanin
15XXN7Q45T
beta-D-Galactopyranoside, (3beta)-solanid-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))-
DTXSID801053062
(22beta)-solanid-5-en-3beta-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-(beta-D-glucopyranosyl-(1->3))-beta-D-galactopyranoside
243-879-8
2-(5-hydroxy-6-(hydroxymethyl)-2-((10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-4-(3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol
3FYV8328OK
CHEBI:9188
RefChem:931952
.alpha.-Solanine
CCRIS 6507
HSDB 3539
EINECS 243-879-8
BRN 0077607
SOLANINE [HSDB]
UNII-15XXN7Q45T
SCHEMBL2380172
.ALPHA.-SOLANINE [MI]
CHEMBL1212997
CCG-208539
beta-D-Galactopyranoside, (3beta)-solanid-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))
Solanid-5-ene, 3-beta-((O-6-deoxy-alpha-L-mannopyranosyl)-O-(beta-D-glucopyranosyl-beta-D-galactopyranosyl)oxy)-
Solanid-5-ene, 3-beta-((O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))-beta-D-galactopyranosyl)oxy)-
F82201
4-21-00-01402 (Beilstein Handbook Reference)
.BETA.-D-GALACTOPYRANOSIDE, (3.BETA.)-SOLANID-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(.BETA.-D-GLUCOPYRANOSYL-(1->3))-