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Adenosine diphosphate (ADP)

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Identification
Molecular formula
C10H15N5O10P2
CAS number
58-64-0
IUPAC name
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3S,4R)-3,4,5-trihydroxytetrahydrofuran-2-yl]methyl hydrogen phosphate
State
State
Adenosine diphosphate is a solid at room temperature.
Melting point (Celsius)
130.00
Melting point (Kelvin)
403.00
Boiling point (Celsius)
85.00
Boiling point (Kelvin)
358.00
General information
Molecular weight
427.20g/mol
Molar mass
427.2010g/mol
Density
1.6800g/cm3
Appearence

Adenosine diphosphate (ADP) typically appears as a white, crystalline powder.

Comment on solubility

Solubility Insights for the Compound

The compound [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3S,4R)-3,4,5-trihydroxytetrahydrofuran-2-yl]methyl hydrogen phosphate exhibits intriguing solubility characteristics that are essential for its potential applications.

Factors Influencing Solubility

The solubility of this compound can be affected by several factors:

  • Polarity: Due to the presence of multiple hydroxyl groups, the compound is likely to have significant polarity, enhancing its ability to dissolve in polar solvents like water.
  • Hydrogen Bonding: The presence of both nucleophilic and electrophilic sites promotes extensive hydrogen bonding with water molecules, further aiding solubility.
  • Structural Configuration: The (R/S) stereochemistry may also influence how easily the compound interacts with its solvent environment.

Expected Solubility Behavior

As a result of these factors, one might expect:

  • The compound to be soluble or at least partially soluble in aqueous solutions.
  • Limited solubility in nonpolar solvents, due to the hydrophilic nature imparted by hydroxyl and phosphate groups.

In summary, the solubility of this complex compound highlights important physiological and chemical interactions, making it a compelling subject for further study. Understanding its solubility can aid in drug formulation and delivery, maximizing therapeutic efficacy.

Interesting facts

Interesting Facts about the Compound

This compound, known for its intricate structure and bioactive properties, showcases the intersection of organic chemistry and biochemistry. Here are some compelling insights into its characteristics and significance:

Biological Importance

1. **Nucleotide Analog**: This compound is structurally related to important nucleotides, playing a role in various biochemical pathways, particularly in nucleic acid metabolism.

2. **Potential as a Drug**: Its unique structure may make it an interesting candidate for drug design, especially in targeting specific cellular pathways associated with diseases.

Synthetic Challenges

3. **Synthesis Complexity**: The synthesis of this compound involves multiple stereocenters, making the process of obtaining it both challenging and fascinating for chemists. Achieving the correct configuration is essential for the desired biological activity.

4. **Use of Protecting Groups**: During synthesis, protecting groups are often used to ensure that the reactive hydroxyl groups are not prematurely involved in side reactions.

Applications in Research

5. **Research Tool**: This compound could be utilized in studying enzyme interactions and mechanisms, particularly those that involve phosphorylated compounds.

6. **Modeling Studies**: It serves as a valuable model in theoretical studies focusing on the behavior of nucleotides in biological systems.

Future Perspectives

As research progresses, understanding compounds like this one can lead to breakthroughs in therapeutic applications, enhancing our comprehension of molecular biology and pharmacology.

In summary, this compound embodies a blend of complexity and utility, inviting researchers to explore its numerous facets in both synthetic chemistry and biological applications.

Synonyms
ADP-D-ribose
CHEBI:16960
Adenosine 5'-diphosphoribose
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methyl hydrogen phosphate
AdoPPRib
ADP-Rib
D-ribofuranose, 5-5'-ester with adenosine 5'-(trihydrogen pyrophosphate)
(Rib5)ppA
A5'pp5Rib
ADP-riboses
CHEMBL2360089
SCHEMBL28045890
NCGC00163321-01
adenosine 5'-[3-(D-ribofuranos-5-O-yl) dihydrogen diphosphate]