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Cyclosporin A

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Identification
Molecular formula
C62H111N11O12
CAS number
59865-13-3
IUPAC name
3-[[6-amino-2-[[3-hydroxy-2-[[1-(5-oxopyrrolidine-2-carbonyl)pyrrolidine-2-carbonyl]amino]propanoyl]amino]hexanoyl]amino]-4-[[2-[[1-benzyl-2-[[1-[[2-[[1-[(1-carbamoyl-3-methylsulfanyl-propyl)carbamoyl]-3-methyl-butyl]amino]-2-oxo-ethyl]carbamoyl]-2-methyl-butyl]amino]-2-oxo-ethyl]amino]-1-methyl-2-oxo-ethyl]amino]-4-oxo-butanoic acid
State
State

Solid: At room temperature, Cyclosporin A is a solid powder.

Melting point (Celsius)
148.00
Melting point (Kelvin)
421.15
Boiling point (Celsius)
619.70
Boiling point (Kelvin)
892.90
General information
Molecular weight
1202.61g/mol
Molar mass
1 202.6110g/mol
Density
1.0890g/cm3
Appearence

Cyclosporin A appears as a white or slightly yellow crystalline powder. It is practically insoluble in water, but soluble in alcohols and other organic solvents.

Comment on solubility

Solubility of 3-[[6-amino-2-[[3-hydroxy-2-[[1-(5-oxopyrrolidine-2-carbonyl)pyrrolidine-2-carbonyl]amino]propanoyl]amino]hexanoyl]amino]-4-[[2-[[1-benzyl-2-[[1-[[2-[[1-[(1-carbamoyl-3-methylsulfanyl-propyl)carbamoyl]-3-methyl-butyl]amino]-2-oxo-ethyl]carbamoyl]-2-methyl-butyl]amino]-2-oxo-ethyl]amino]-1-methyl-2-oxo-ethyl]amino]-4-oxo-butanoic acid

C62H111N11O12

The solubility of the compound can be quite intricate given its complex structure. Here are some key points regarding its solubility:

  • Polarity: The presence of multiple amino groups and hydroxyl functionalities contributes to enhanced polarity, likely improving solubility in polar solvents such as water.
  • Molecular Size: Its substantial size may hinder solubility due to steric hindrance despite the presence of soluble functional groups.
  • pH Dependency: As a compound with acidic groups, solubility may vary with pH; a more basic environment could aid in deprotonation, thus enhancing solubility.
  • Hydrogen Bonding: The ability to form hydrogen bonds increases the likelihood of dissolution in polar solvents.
  • Solvent Type: It may exhibit varying solubility in different solvents; more research is needed but polar organic solvents may provide better solubility when compared to non-polar solvents.

In conclusion, while the solubility of this compound is influenced by multiple factors including its structural components and environmental conditions, it's likely to exhibit a moderate to high solubility in polar solvents based on its functional groups. As noted, empirical testing is critical to ascertain precise solubility metrics.

Interesting facts

Interesting Facts about 3-[[6-amino-2-[[3-hydroxy-2-[[1-(5-oxopyrrolidine-2-carbonyl)pyrrolidine-2-carbonyl]amino]propanoyl]amino]hexanoyl]amino]-4-[[2-[[1-benzyl-2-[[1-[[2-[[1-[(1-carbamoyl-3-methylsulfanyl-propyl)carbamoyl]-3-methyl-butyl]amino]-2-oxo-ethyl]carbamoyl]-2-methyl-butyl]amino]-2-oxo-ethyl]amino]-1-methyl-2-oxo-ethyl]amino]-4-oxo-butanoic acid

This compound represents a complex and fascinating example in the field of medicinal chemistry. Characterized by its intricate structure, it incorporates multiple functional groups that suggest potential interactions within biological systems. Here are some intriguing aspects of this chemical compound:

  • Peptide Nature: The presence of multiple amine and carboxylic acid functional groups indicates that this compound may function analogously to peptides, potentially influencing protein interactions.
  • Pharmacophore Potential: The diverse arrangements of amino acids and functional side chains make this compound a valuable candidate for drug design, especially in targeting specific receptors or pathways.
  • Multifunctionality: Comprising numerous functional groups allows it to engage in a variety of biological activities, which may include:
    • Antimicrobial properties
    • Anticancer effects
    • Neuroprotective activities
  • Structural Complexity: The detailed structure not only makes it a challenge for synthesis but also a subject of interest for researchers looking to explore structure-activity relationships (SAR).
  • Potential for Modification: The many functional groups present allow for further chemical modifications, which can lead to derivatives with enhanced efficacy or reduced side effects.

This compound exemplifies how a complex molecular architecture can lead to promising therapeutic agents, encouraging ongoing research and investigation into its properties and effects. Its potential applications highlight the intersection of chemistry and biology, driving innovation in the development of new drugs.

Synonyms
69-25-0
Eledoisin acetate salt
SCHEMBL158144
69-25-0(free acid basis)
AKOS015896028
AC-8915
AS-84122
FE108742
NS00120289
F85423
L000875