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Abacavir

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Identification
Molecular formula
C14H18N6O
CAS number
136470-78-5
IUPAC name
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]tetrahydrofuran-3,4-diol
State
State

At room temperature, abacavir is a solid.

Melting point (Celsius)
165.00
Melting point (Kelvin)
438.15
Boiling point (Celsius)
279.80
Boiling point (Kelvin)
552.95
General information
Molecular weight
286.33g/mol
Molar mass
286.3320g/mol
Density
1.8900g/cm3
Appearence

Abacavir is an off-white to pale yellow solid. It typically appears as a crystalline powder.

Comment on solubility

Solubility of (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]tetrahydrofuran-3,4-diol

The solubility of complex organic compounds like (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]tetrahydrofuran-3,4-diol can depend on several factors, including molecular structure, functional groups, and environmental conditions.

Factors Influencing Solubility

  • Polarity: The presence of hydroxymethyl groups suggests potential for hydrogen bonding, which may enhance solubility in polar solvents like water.
  • Functional Groups: The purine base and amine functionalities could also contribute to interactions in aqueous environments, possibly leading to higher solubility due to better solvation.
  • Molecular Weight: Higher molecular weight may hinder solubility in some solvents, reflecting a balance between structural complexity and solvent interactions.

In general, the solubility of compounds like this one can be quite variable and is often deduced empirically. Knowing the solvent properties or conducting solubility tests is key in determining how well this compound will dissolve in different solutions.

As solubility is a critical parameter in applications ranging from pharmaceutical formulations to chemical synthesis, understanding its nature can aid in optimizing its use in various fields.

Interesting facts

Interesting Facts About (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]tetrahydrofuran-3,4-diol

This fascinating compound is notable not only for its complex structure but also for its possible applications in the realm of biochemistry. Here are some intriguing facts:

  • Structure and Stereochemistry: This compound showcases a unique stereochemical arrangement, with multiple chiral centers. The specific configuration (2R,3S,4R,5R) contributes to its biological activity, showing how small changes in structure can lead to significant differences in function.
  • Biological Relevance: The purine moiety present in the compound indicates its relationship to nucleotides, which are essential for various biological processes, including DNA and RNA synthesis.
  • Medicinal Chemistry: Compounds featuring such structural characteristics are often the subject of medicinal chemistry studies, as they may possess properties useful in drug development, specifically targeting diseases at the cellular level.
  • Potential Applications: Research is ongoing into compounds like this one, which could serve as inhibitors in biological pathways or be utilized in designing targeted therapies for diseases such as cancer or viral infections.
  • Natural Occurrence: Many complex carbohydrates and nucleosides share similar structures, pointing to the compound's potential existence or importance in natural systems, possibly even as a metabolic intermediate.

As chemists continue to explore the diverse world of compounds, this specific molecule stands out as a testament to the intricate relationships between structure and biological function. Its study could unveil new avenues for therapeutic interventions and deepen our understanding of molecular biology.

Synonyms
7724-76-7
Riboprine
N6-(3-Methyl-2-butenyl)adenosine
N6-Isopentenyladenosine
Isopentenyladenosine
2iPA
Riboprina
N6-(2-Isopentenyl)adenosine
Isopentenyladenosine riboside
ADENOSINE, N-(3-METHYL-2-BUTENYL)-
Riboprinum
2-IPA
N-(3-Methyl-2-butenyl)adenosine
N6-ISOPENTENYLADENOSINE-D6
Isopentenyl adenosine
6-(gamma,gamma-Dimethylallylamino)purine riboside
6-(3-Methyl-2-butenylamino)purine riboside
Dimethylallyladenosine
N-(3-methylbut-2-en-1-yl)adenosine
Isopentenyl adenine riboside
NSC-105546
8EU82FAZ5J
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
N6-(2-isopentenyl)-adenosine
DTXSID1057828
N(6)-(2-isopentenyl)adenosine
CHEBI:62881
N-(3-methylbut-2-enyl)adenosine
N(6)-(3-methyl-2-butenyl)adenosine
N(6)-(Delta(2)-isopentenyl)adenosine
SQ 22558
ZK 20 242
6-(3,3-Dimethylallylamino)-9-(b-D-ribofuranosyl)purine
Riboprine [USAN:INN]
Riboprinum [INN-Latin]
6-N-((3-Methyl-2-butenyl)amino)-9-.beta.-D-ribofuranosyl-9H-purine
MFCD00005741
Riboprina [INN-Spanish]
2iP Riboside
(2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-((3-methylbut-2-en-1-yl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
i6a
N(sup 6)-Isopentenyladenosine
N(sup 6)-Dimethylallyladenosine
EINECS 231-771-3
N(sup 6)-(2-Isopentenyl)adenosine
UNII-8EU82FAZ5J
NSC 105546
Riboprin
N(sup 6)-(delta(sup 2)-Isopentenyl)adenosine
Ribosyl-deoxyzeatin
ZIR
RIBOPRINE [INN]
6-N-((3-Methyl-2-butenyl)amino)-9beta-D-ribofuranosylpurine
9beta-D-Ribofuranosyl-9H-purine, N-(3-methyl-2-butenylamino)-
Riboprine (USAN/INN)
N6-Dimethylallyladenosine
RIBOPRINE [USAN]
6-N-((3-Methyl-2-butenyl)amino)-9-beta-D-ribofuranosyl-9H-purine
SCHEMBL4599
6-N-((3-Methyl-2-butenyl)amino)-9.beta.-D-ribofuranosylpurine
CHEMBL452867
DTXCID2031617
Tox21_113776
AKOS016009606
CS-W011925
DB11933
DS-5147
HY-W011209
ND08001
NCGC00253650-01
BP-58623
adenosine, N(6)-(3-methyl-2-butenyl)-
Adenosine, N-(3-methyl-2-buten-1-yl)-
CAS-7724-76-7
2iP Riboside; N6-(2-Isopentenyl)adenosine
N6-(.DELTA.2-Isopentenyl)adenine riboside
N6-(3,3-Dimethylallylamino)purine riboside
N6-(.gamma.,.gamma.-Dimethylallyl)adenosine
NS00037896
D05726
Q973089
SR-01000883994
SR-01000883994-1
6-( gamma , gamma -Dimethylallylamino)purine riboside
N6-(| currency2-isopentenyl)adenosine pound IPA)