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Cytarabine

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Identification
Molecular formula
C9H13N3O5
CAS number
147-94-4
IUPAC name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-hydroxy-hexahydropyrimidin-2-one
State
State

At room temperature, Cytarabine is a solid.

Melting point (Celsius)
212.00
Melting point (Kelvin)
485.15
Boiling point (Celsius)
260.00
Boiling point (Kelvin)
533.15
General information
Molecular weight
243.22g/mol
Molar mass
243.2190g/mol
Density
1.6000g/cm3
Appearence

Cytarabine typically appears as a white to off-white crystalline powder.

Comment on solubility

Solubility of 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-hydroxy-hexahydropyrimidin-2-one

The solubility of this complex compound can be influenced by various factors due to its intricate structure. In general, the presence of multiple hydroxyl groups, such as those found in its chemical formula, can significantly enhance the compound's solubility in polar solvents. Here are some key points regarding its solubility:

  • Polar Solvents: The compound is likely to be more soluble in water and other polar solvents due to its hydroxyl groups that can form hydrogen bonds.
  • Non-Polar Solvents: The solubility in non-polar solvents is expected to be low, given the hydrophilic nature of the hydroxyl functional groups.
  • Temperature Dependence: Solubility is generally temperature-dependent; increasing temperature often increases the solubility of such compounds.
  • pH Influence: The solubility may also be affected by the pH of the solution, especially if the compound has any ionizable groups.

In summary, while the solubility characteristics might hint at high solubility in polar environments, factors such as solvent choice, temperature, and pH should be carefully considered for accurate predictions. The intricate balance of hydrophilic and hydrophobic elements in this compound underscores the need for experimental validation to fully understand its solubility profile.

Interesting facts

Interesting Facts about 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-hydroxy-hexahydropyrimidin-2-one

This fascinating compound, often recognized in the realm of organic chemistry, offers a rich tapestry of structural characteristics and potential applications. Here are some key insights:

  • Sugar and Nucleobase Connection: The compound features a unique combination of a sugar moiety, derived from tetrahydrofuran, and a pyrimidine structure. This duality is a common theme in biologically significant compounds such as nucleosides.
  • Biological Significance: The hydroxyl groups present in the structure enhance its interaction with biological systems. Compounds with similar configurations often play critical roles in enzyme catalysis and cellular signaling pathways.
  • Chirality Matters: The stereochemistry indicated by the (2R,3R,4S,5R) notation highlights the importance of chirality in bioactivity. Enantiomers of similar molecules can exhibit vastly different biological effects, making stereochemical configuration a crucial factor in drug design.
  • Potential Applications: Researchers are investigating the use of compounds with this type of structure in pharmaceuticals, especially in the development of antiviral agents, owing to the functional groups facilitating interactions with biological targets.

As chemistry students and scientists, understanding the complexities of such compounds not only broadens our knowledge of organic chemistry but also opens pathways to innovate in medicinal chemistry and drug discovery. As one renowned chemist put it, "Every molecule tells a story; it's our job to decipher it."

Synonyms
TETRAHYDROURIDINE
18771-50-1
NSC-112907
0NIZ8H6OL8
NSC 112907
NSC-112907-D
NSC112907
U-23284
2(1H)-pyrimidinone, tetrahydro-4-hydroxy-1-beta-D-ribofuranosyl-
3,4,5,6-Tetrahydrouridine
3,4,5,6-Tetrahydrouridine (>80%)
CHEMBL2311128
1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-hydroxytetrahydropyrimidin-2(1H)-one
U 23284
2(1H)-Pyrimidinone, tetrahydro-4-hydroxy-1-.beta.-D-ribofuranosyl-
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-hydroxy-hexahydropyrimidin-2-one
Uridine, 3,4,5,6-tetrahydro-
MFCD00063468
BRN 0752319
UNII-0NIZ8H6OL8
SCHEMBL587704
3,4,5, 6-Tetrahydrouridine
orb1307675
BDBM50421666
HY-15345A
AKOS032953792
DB12484
AS-86075
DA-68078
NT171853
CS-0130206
F77615
BRD-A86248581-001-01-4
Q27237004
4-hydroxy-1-beta-D-ribofuranosyl-tetrahydro-2(1H)-pyrimidinone
1-(.BETA.-D-RIBOFURANOSYL)-4-HYDROXYTETRAHYDRO-1(1H)-PYRIMIDINONE
2(1H)-Pyrimidinone, tetrahydro-4-hydroxy-1-.beta.-D-ribofuranosyl- ( )