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Zidovudine

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Identification
Molecular formula
C10H13N5O4
CAS number
30516-87-1
IUPAC name
[(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxo-pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl dihydrogen phosphate
State
State

At room temperature, Zidovudine is a solid substance, usually found in crystalline or powder form.

Melting point (Celsius)
125.50
Melting point (Kelvin)
398.65
Boiling point (Celsius)
290.00
Boiling point (Kelvin)
563.15
General information
Molecular weight
267.24g/mol
Molar mass
267.2430g/mol
Density
1.6940g/cm3
Appearence

Zidovudine typically appears as a white or off-white crystalline powder.

Comment on solubility

Solubility of [(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxo-pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl dihydrogen phosphate

The solubility of the compound [(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxo-pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl dihydrogen phosphate is quite intriguing. This complex molecule exhibits unique characteristics that influence its solubility in various solvents.

Factors Affecting Solubility

  • Hydroxyl Groups: The presence of multiple hydroxyl groups (-OH) can enhance solubility in polar solvents such as water, as these groups can form hydrogen bonds with water molecules.
  • Phosphate Group: The dihydrogen phosphate moiety contributes to increased solubility in aqueous environments due to its ionic nature.
  • Hydrophobic Regions: The tetrahydrofuran ring and the pyrimidine structure may introduce some hydrophobic characteristics, which can limit solubility in highly polar solvents.

In general, the solubility characteristics can be summarized as follows:

  1. Aqueous Solubility: Likely soluble due to the presence of polar functional groups.
  2. Organic Solvents: Solubility may vary; compounds with larger hydrophobic regions may exhibit limited solubility.
  3. Temperature Influence: Elevated temperatures typically increase the solubility of solid compounds in liquids.

In conclusion, the solubility of this compound is primarily dictated by the balance between its polar and non-polar features, making it a subject of interest in both pharmacological and chemical research.

Interesting facts

Interesting Facts about [(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxo-pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl dihydrogen phosphate

This multifaceted compound serves as a prime example of the intricate relationship between structure and biological activity. Here are some captivating insights:

  • Biological Activity: This compound is a derivative of nucleosides, crucial for biological processes like DNA and RNA synthesis. The presence of both hydroxyl and amino groups hints at potential interactions with enzymes and other biological molecules.
  • Pharmaceutical Relevance: Compounds that resemble nucleotide structures often exhibit antiviral or anticancer properties. They can act as substrates or inhibitors in various biochemical pathways, making them valuable in drug development.
  • Synthetic Pathways: The synthesis of this compound often involves intricate multistep processes, highlighting the challenges and creativity involved in organic chemistry. Its formation can provide insights into reaction mechanisms and the stability of various functional groups.
  • Structural Diversity: The stereochemistry indicated in its name (with the specific R/S configurations) adds another layer of complexity. The configuration can greatly influence its biological activity, demonstrating the principle that structure dictates function.
  • Application in Research: Researchers utilize this compound in studies to better understand interactions at a molecular level. It can serve as a model for developing new therapeutics targeting specific biosynthetic pathways.

Overall, the study of [(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxo-pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl dihydrogen phosphate not only showcases the beauty of chemical compounds but also opens doors to innovations within pharmacology and biochemistry. As the field advances, compounds of this nature will continue to play a significant role in our understanding of life at the molecular level.

Synonyms
4988-54-9
N-Hydroxycytidine 5'-(Dihydrogen Phosphate)
[(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate
N4-OH-CMP
BRN 0847593
N(sup 4)-Hydroxycytidine monophosphate
CYTIDINE, N-HYDROXY-, 5'-(DIHYDROGENPHOSPHATE)
CHEMBL2221214
DTXSID10964462
AT28496
EN300-33051129
N-hydroxycytidine 5'-(dihydrogen phosphate) tautomer
Q27451723
4-(Hydroxyamino)-1-(5-O-phosphonopentofuranosyl)pyrimidin-2(1H)-one
N4-OH-CMP, N-Hydroxycytidine 5'-(Dihydrogen Phosphate), Molnupiravir monophosphate
((2R,3S,4R,5R)-3,4-Dihydroxy-5-(4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
((2R,3S,4R,5R)-3,4-Dihydroxy-5-(4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyldihydrogenphosphate
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxo-1,2-dihydropyrimidin-1-yl]oxolan-2-yl]methoxy}phosphonic acid