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Linaclotide

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Identification
Molecular formula
C59H79N15O21
CAS number
851199-59-2
IUPAC name
methyl 1-[3-methyl-2-[[3-(propylcarbamoyl)oxirane-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carboxylate
State
State

Linaclotide is a solid at room temperature. While it is stable under normal conditions, it needs to be stored carefully, away from light and moisture to prevent decomposition.

Melting point (Celsius)
218.00
Melting point (Kelvin)
491.15
Boiling point (Celsius)
469.15
Boiling point (Kelvin)
742.30
General information
Molecular weight
1166.34g/mol
Molar mass
507.6030g/mol
Density
1.3063g/cm3
Appearence

Linaclotide is a white to off-white powder. It is practically insoluble in water, slightly soluble in methanol, and soluble in dimethyl sulfoxide.

Comment on solubility

Solubility of Methyl 1-[3-methyl-2-[[3-(propylcarbamoyl)oxirane-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carboxylate

The solubility of the compound with the chemical formula C59H79N15O21 can be quite intricate due to its complex molecular structure. Here are key points regarding its solubility properties:

  • Polar and Non-Polar Interactions: This compound contains a variety of functional groups that can enhance interaction with both polar and non-polar solvents. This duality may lead to moderate solubility in various organic solvents such as methanol and ethanol.
  • Hydrogen Bonding: The presence of multiple amine and carboxyl groups suggests that hydrogen bonding could significantly influence its solubility, potentially increasing solubility in polar solvents.
  • Influence of Molecular Weight: With a relatively high molecular weight, solubility may be limited in water, and it may require the presence of surfactants or co-solvents to increase its solubility.
  • Temperature Dependency: The solubility could be affected by temperature variations; thus, higher temperatures might improve solubility in specific solvents.
  • pH Sensitivity: Given the carboxyl functional group, the solubility could vary significantly with changes in pH, making it potentially more soluble in alkaline conditions.

Understanding the solubility characteristics of this compound is essential for applications in pharmaceutical formulations, where solubility can greatly impact bioavailability and efficacy of the drug.

Interesting facts

Interesting Facts about Methyl 1-[3-methyl-2-[[3-(propylcarbamoyl)oxirane-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carboxylate

Methyl 1-[3-methyl-2-[[3-(propylcarbamoyl)oxirane-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carboxylate is a fascinating compound with multiple points of interest for both chemists and biochemists. Here are some highlights:

  • Complex Structure: The compound boasts a complex molecular framework that includes multiple functional groups. This complexity can lead to intriguing properties and potential applications in the field of medicinal chemistry.
  • Carbamoyl Feature: The presence of the carbamoyl group indicates the potential for this compound to participate in various biological processes, possibly acting as a bioligand. This makes it worthy of investigation in drug design and development.
  • Oxirane Ring: The oxirane moiety (commonly known as an epoxide) adds to the compound's reactivity, engaging in nucleophilic ring-opening reactions that are integral to synthetic organic chemistry.
  • Potential Bioactivity: Due to its intricate structure, this compound warrants exploration for its pharmacological properties, potentially offering solutions for treating diseases affected by specific metabolic pathways.
  • Synthetic Routes: The synthesis of such a compound may offer insights into innovative synthetic methods, especially involving chiral centers and stereochemistry, which are crucial in designing efficient and environmentally friendly chemical processes.

As stated by a leading chemist, "Understanding the nuances of complex compounds such as this can pave the way for groundbreaking advancements in pharmaceuticals." Exploring Methyl 1-[3-methyl-2-[[3-(propylcarbamoyl)oxirane-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carboxylate deepens our understanding of the intersections between structure and biological activity.

Synonyms
L-trans-epoxysuccinyl-Ile-pro-ome propylamide
Methyl N-({(2s,3s)-3-[(Propylamino)carbonyl]oxiran-2-Yl}carbonyl)-L-Isoleucyl-L-Prolinate
Bio1_001277
CBiol_002013
SCHEMBL14645506
Bio1_000299
Bio1_000788
IEC-4323-V
METHYL 1-(3-METHYL-2-{[3-(PROPYLCARBAMOYL)OXIRAN-2-YL]FORMAMIDO}PENTANOYL)PYRROLIDINE-2-CARBOXYLATE