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Zidovudine

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Identification
Molecular formula
C10H13N5O4P
CAS number
30516-87-1
IUPAC name
[(2R,3S,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
State
State

At room temperature, zidovudine is found as a solid. It is typically used in its crystalline form in pharmaceuticals.

Melting point (Celsius)
125.00
Melting point (Kelvin)
398.15
Boiling point (Celsius)
185.00
Boiling point (Kelvin)
458.15
General information
Molecular weight
267.24g/mol
Molar mass
267.2410g/mol
Density
2.1000g/cm3
Appearence

Zidovudine appears as a white to beige, odorless crystalline solid. Its form can vary from fine powder to larger crystalline structures.

Comment on solubility

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

The solubility of [(2R,3S,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate can be discussed from several angles:

  • Polarity: The presence of hydroxyl groups and phosphate groups typically indicates a polar nature, which can enhance solubility in polar solvents like water.
  • Hydrogen Bonding: The ability to form hydrogen bonds with water molecules suggests that this compound may dissolve readily in aqueous environments, making it relevant for biological systems.
  • pH Dependency: The solubility may vary with the pH of the solution, as the structure contains both an amino group and a phosphate group, which can be protonated or deprotonated depending on the surrounding conditions.
  • Temperature Effects: Generally, an increase in temperature can enhance solubility, particularly for organic compounds like this one. This is significant in applications where temperature can be controlled.

In essence, the solubility profile of this compound suggests good solubility in aqueous environments, driven by its polar characteristics and potential for hydrogen bonding. This property is essential for its transport and function in biological contexts.

Interesting facts

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

This compound is a fascinating example of a molecule that combines multiple functional groups, showcasing the complexity often found in organic chemistry. Here are some noteworthy points:

  • Biological Importance: This compound features a pyrimidine moiety, which is crucial in the structure of nucleic acids. Pyrimidines are fundamental components in the genetic material of organisms, making this compound potentially significant in biological research.
  • Phosphate Group: The presence of a dihydrogen phosphate group suggests that this compound may play a role in biochemical pathways, particularly those involving energy transfer, nucleotide synthesis, and signaling. Phosphate groups are notorious for being involved in cellular energy processes, such as ATP synthesis.
  • Stereochemistry: The stereocenters indicated by (2R,3S,5R) in the name hint at the compound's chiral nature. Chirality can affect the biological activity of molecules, especially in pharmaceuticals, where specific configurations may interact differently within biological systems.
  • Potential Uses: Analyzing this compound's structure might reveal its utility in drug development, possibly targeting specific enzymes or providing therapeutic benefits in genetic disorders due to its structural similarities to nucleobases.
  • Research Frontier: As scientists continue to explore nucleic acid analogs, the potential application of this compound in gene therapy and as a research tool in molecular biology become increasingly significant.

In the words of renowned chemist Linus Pauling, "The best way to have a good idea is to have a lot of ideas." This compound certainly embodies the essence of innovation in synthetic chemistry and its application to solving biological questions.

Overall, the multifunctional aspects of [(2R,3S,5R)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate highlight the intricate relationship between chemical structure and biological function, paving the way for exciting research and discoveries in the field of chemistry.

Synonyms
W7A9174XQL
CHEBI:15918
2'-deoxycytosine 5'-monophosphate
deoxycytidine 5'-monophosphate
213-849-9
1032-65-1
dCMP
2'-Deoxycytidine-5'-monophosphoric acid
2'-DEOXYCYTIDINE-5'-MONOPHOSPHATE
deoxycytidylic acid
deoxycytidine monophosphate
2'-Deoxycytidine 5'-monophosphate
5'-Cytidylic acid, 2'-deoxy-
Deoxycytidylate
2'-deoxy-5'-cytidylic acid
2'-Deoxycytidine 5'-Monophosphate Hydrate
[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
MFCD00006546
deoxycytidine-phosphate
((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
{[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
Deoxycytidine-5'-monophosphoric acid
2_-Deoxycytidine 5_-Monophosphate
UNII-W7A9174XQL
1nja
1njc
1nje
EINECS 213-849-9
Oligodeoxycytidylic acid d(pc)3*ammonium
13085-50-2
1beta-Deoxyribofuranosylcytosine-5'-phosphate,d
SCHEMBL48317
2'-Deoxycytidinemonophosphate
2'-deoxycytidine-5'-phosphate
CHEMBL374699
deoxycytidine dihydrogen phosphate
DTXSID20908251
HY-W009216R
2'-Deoxycytidine-5'-monophosphorate
HG1127
s3268
AKOS015892753
2'-Deoxycytidine-5'-monophosphoricacid
CS-W009932
DB03798
HY-W009216
ND02993
2 inverted exclamation marka-Deoxycytidine 5 inverted exclamation marka-monophosphate
29795-73-1
AS-64039
BP-58812
2a(2)-Deoxycytidine-5a(2)-monophosphate
2'-Deoxycytidine-5'-monophosphatefree acid
D3673
NS00069402
C00239
2'-DEOXYCYTIDINE-5'-MONOPHOSPHATE FREE ACID
2'-Deoxycytidine-5'-monophosphoric acid (Standard)
Q2742455
2'-Deoxycytidine 5'-monophosphate, Sigma Grade, >=95.0%