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Flavin adenine dinucleotide

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Identification
Molecular formula
C27H33N9O15P2
CAS number
146-14-5
IUPAC name
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] [(2S,3R,4R)-5-(7,8-dimethyl-2,4-dioxo-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] hydrogen phosphate
State
State

At room temperature, flavin adenine dinucleotide is generally found in a solid state. It is stable and does not decompose readily, allowing it to be used biologically as a redox cofactor. It is most commonly found in a hydrated form when isolated.

Melting point (Celsius)
282.00
Melting point (Kelvin)
555.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
785.56g/mol
Molar mass
0.0000g/mol
Density
0.7012g/cm3
Appearence

Flavin adenine dinucleotide (FAD) typically appears as a yellow or yellow-orange solid. It may be available in the form of a powder or crystalline substance, depending on its preparation and purity. The intensity of the yellow color is due to the isoalloxazine ring of the flavin moiety, which absorbs visible light strongly.

Comment on solubility

Solubility of the Compound

The solubility of the compound identified as [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] [(2S,3R,4R)-5-(7,8-dimethyl-2,4-dioxo-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] hydrogen phosphate can be quite intricate due to its complex structure. The following factors significantly influence its solubility:

  • Polarity: The presence of multiple hydroxyl groups in the molecule likely enhances its ability to interact with polar solvents, such as water, making it more soluble.
  • Hydrogen Bonding: The compound’s hydroxyl (-OH) groups can participate in hydrogen bonding, further increasing solubility in aqueous environments.
  • Intramolecular Interactions: The conformational flexibility enabled by the tetrahydrofuran and pentyl chains may impact solvation dynamics, potentially affecting crystal packing and dissolution rates.
  • pH Dependence: Being a phosphate, solubility may be influenced by the pH of the solution, with enhanced solubility at certain pH levels due to protonation or deprotonation of the phosphate groups.

In summary, it can be stated that this compound is likely to be moderately soluble in polar solvents, particularly water, owing to the multifaceted interaction involving its functional groups. Understanding these solubility characteristics is crucial for applications and formulations where this compound may be utilized.

Interesting facts

Exploring the Fascinating World of Phosphorylated Compounds

The compound under discussion represents a complex molecule that blends various functional groups and stereochemistry, showcasing the intricate nature of biochemical compounds. Here are some notable aspects:

  • Chemical Diversity: This molecule exhibits a rich tapestry of elements and structures. The presence of both a tetrahydrofuran ring and a benzo[g]pteridin structure highlights how nature often combines different structures to achieve specific biological functions.
  • Stereochemical Complexity: With multiple stereocenters, this compound exemplifies chirality in organic chemistry. Chirality is fundamental in biological systems since the two enantiomers of a chiral molecule can have drastically different effects in biological contexts.
  • Biological Relevance: Compounds such as this one often play significant roles in cellular signaling pathways or as intermediates in metabolic processes. They may interact with enzymes or nucleic acids, hinting at their potential importance in pharmacology and therapeutics.
  • Role of Phosphorylation: The phosphate group in this compound is crucial. Phosphorylation is a common regulatory mechanism in biochemistry, involving the addition of a phosphate group to proteins or other molecules, which can regulate activity, localization, and interaction with other biomolecules.

As we dive deeper into the study of such compounds, we uncover the profound interconnectedness of chemical structure, function, and biological systems. Each layer of complexity adds to the vast puzzle that scientists strive to piece together in the field of biochemistry.

Synonyms
flavitan
Flavinat
Flamitajin B
Flanin F
Flavin adenin dinucleotide [JAN]
Adenine-riboflavin dinuceotide
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] [(2S,3R,4R)-5-(7,8-dimethyl-2,4-dioxo-benzo[g]pteridin-10-yl)-2,3,4-trihydroxy-pentyl] hydrogen phosphate
(((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)methoxy-hydroxy-phosphoryl) ((2S,3R,4R)-5-(7,8-dimethyl-2,4-dioxo-benzo(g)pteridin-10-yl)-2,3,4-trihydroxy-pentyl) hydrogen phosphate
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