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Spinosyn A

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Identification
Molecular formula
C41H65NO10
CAS number
131929-60-7
IUPAC name
(2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxo-cyclopenten-1-yl)carbamoyl]tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-4-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-4-carbamoyloxy-3-hydroxy-6-[hydroxy-[(2R)-2-hydroxy-3-oxo-3-(4,9,9,15,19-pentamethyl-12-methylene-icosa-3,7,14,18-tetraenoxy)propoxy]phosphoryl]oxy-3-methyl-tetrahydropyran-2-carboxylic acid
State
State

Spinosyn A is typically found as a solid at room temperature.

Melting point (Celsius)
129.00
Melting point (Kelvin)
402.15
Boiling point (Celsius)
700.00
Boiling point (Kelvin)
973.15
General information
Molecular weight
970.47g/mol
Molar mass
970.4730g/mol
Density
1.4100g/cm3
Appearence

Spinosyn A appears as fine, colorless crystals or as crystalline powder. It is often slightly off-white when impure.

Comment on solubility

Solubility of the Compound

The solubility of the compound, (2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxo-cyclopenten-1-yl)carbamoyl]tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-4-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-4-carbamoyloxy-3-hydroxy-6-[hydroxy-[(2R)-2-hydroxy-3-oxo-3-(4,9,9,15,19-pentamethyl-12-methylene-icosa-3,7,14,18-tetraenoxy)propoxy]phosphoryl]oxy-3-methyl-tetrahydropyran-2-carboxylic acid, is influenced by several factors:

  • Hydrophilicity: The presence of multiple hydroxyl groups (–OH) generally increases solubility in polar solvents such as water.
  • Hydrophobic Regions: The cyclopentenyl and hydrophobic carbon chains may decrease overall solubility in water due to their tendency to aggregate.
  • Network of Functional Groups: Amido and hydroxy groups can form hydrogen bonds, which often enhances solubility in aqueous environments.

In summary, the solubility of this compound can be characterized as potentially moderate to high in polar solvents due to hydrophilic groups present, but may face challenges in fully dissolving due to its complex hydrophobic structures.


Given its intricate structure, one may also consider that "the balance between hydrophilic and hydrophobic components governs its solubility profile." Thus, predicting solubility requires a nuanced understanding of these competing interactions.

Interesting facts

Interesting Facts about (2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-...-2-carboxylic acid

This complex compound belongs to a unique class known for their intricate structures and biological significance. Compounds like this one are often studied for their potential applications in pharmaceuticals and biotechnology. Here are some fascinating insights:

  • Structural Complexity: The elaborate arrangement of functional groups and stereochemical centers makes this compound a subject of interest in stereochemistry. The presence of multiple tetrahydropyran rings contributes to a rich diversity in its chemical behavior.
  • Biological Relevance: Many compounds with similar structures are known to exhibit significant biological activity. Their derivatives may act as enzyme inhibitors or as antibiotic agents. As such, understanding compounds like this one can lead to the discovery of new drug candidates.
  • Carbamate Chemistry: The presence of carbamoyl groups suggests potential applications in medicinal chemistry, as carbamates are known for their role in drug design, particularly as prodrugs that increase bioavailability.
  • Research Applications: Scientists are keen to explore the synthesis methods for such compounds, as developing efficient strategies can pave the way for producing similar molecules on a larger scale.
  • Natural Sources: It is crucial to note that many complex compounds are harvested from natural sources, making them valuable in pharmacognosy and drug discovery.

As researchers unravel the specific mechanisms and functions of such compounds, we continue to expand our knowledge on the important intersections between chemistry, biology, and medicine. The ongoing exploration of these intricate molecules promises exciting advancements in therapeutic strategies.