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Adenosine

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Identification
Molecular formula
C10H13N5O4
CAS number
58-61-7
IUPAC name
(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
State
State

At room temperature, adenosine is typically found as a solid. It is commonly used in biochemical research as it plays a crucial role in energy transfer as adenosine triphosphate (ATP) and in signal transduction as cyclic adenosine monophosphate (cAMP).

Melting point (Celsius)
234.00
Melting point (Kelvin)
507.15
Boiling point (Celsius)
580.00
Boiling point (Kelvin)
853.15
General information
Molecular weight
267.24g/mol
Molar mass
267.2410g/mol
Density
1.5100g/cm3
Appearence

Adenosine is a white crystalline powder. It is odorless or has a slight ammonia smell. This compound is notable for its presence in nucleic acids such as DNA and RNA when it forms part of adenine nucleotides.

Comment on solubility

Solubility of (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

The solubility characteristics of the compound (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol can be intriguing due to its complex molecular structure. Here are some key considerations:

  • Polar Protein Nature: Given the presence of hydroxyl groups and nitrogen-containing bases, this compound is likely to exhibit significant polarity.
  • Water Solubility: Compounds that contain hydroxymethyl and aminopurin functional groups often have enhanced solubility in water, facilitating interactions in biological systems.
  • pH Dependence: The solubility could also be influenced by pH levels. The amine group can become protonated under acidic conditions, potentially affecting overall solubility.
  • Hydrogen Bonding: The ability to form hydrogen bonds is a vital aspect that could increase solubility in polar solvents.

Overall, the solubility of (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol appears favorable in aqueous environments, making it a compound of interest in biochemical applications. However, further experimental data would elucidate its exact solubility profile.

Interesting facts

Interesting Facts about (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

This unique compound belongs to a class of molecules rich in biological activity, particularly in the realm of nucleoside analogs. Compounds like this one are often studied for their potential therapeutic effects and role in biochemistry.

  • Nucleoside Analog: This compound features a purine base, resembling DNA and RNA components. As a nucleoside analog, it has potential as an antiviral or anticancer agent by interfering with nucleic acid synthesis.
  • Structure and Chirality: The specific stereochemistry indicated by the (2R,3S,5R) configuration is critical. Chirality influences interactions with biological systems, making it a focal point in drug design.
  • Hydroxymethyl Group: The presence of the hydroxymethyl substitution enhances its reactivity and solubility, influencing its biological activity and pharmacokinetics.
  • Research Perspectives: Scientists are keen on investigating the effects of this compound in cellular environments, focusing on its potential to modulate pathways involved in cancer and viral infections.

Moreover, as highlighted by some researchers, "Understanding the structure-activity relationships can lead to safer and more effective therapeutic agents." This emphasizes the importance of compounds like (2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol in medicinal chemistry.

Overall, this compound exemplifies the intricate relationship between chemical structure and biological function, inviting further exploration and discoveries in the field of pharmaceutical chemistry.

Synonyms
2'-deoxyadenosine
deoxyadenosine
958-09-8
2-Deoxyadenosine
Adenyldeoxyriboside
Adenine deoxyribose
ADENOSINE, 2'-DEOXY-
(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
Desoxyadenosine
Adenine deoxy nucleoside
CCRIS 1782
CHEBI:17256
AI3-52383
(2R,3S,5R)-5-(6-Aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
2-deoxy-adenosine
EINECS 213-488-7
NSC 83258
NSC 141848
NSC 143510
BRN 0091015
P582C98ULC
beta-D-erythro-Pentofuranoside, adenine-9 2-deoxy-
(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
9H-Purin-6-amine, 9-(2-deoxy-beta-D-ribofuranosyl)-
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine
9H-Purin-6-amine, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)-
beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-
DTXSID10883624
4-26-00-03589 (Beilstein Handbook Reference)
9-(2-deoxy-beta-D-ribofuranosyl)-9H-purin-6-amine
NSC-83258
NSC-141848
NSC-143510
2'-DEOXYADENOSINE [USP IMPURITY]
9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine
adenine-9 2-deoxy-b-D-erythro-Pentofuranoside
Adenine-9 2-deoxy-beta-D-erythro-Pentofuranoside
9-(2-deoxy-b-D-ribofuranosyl)-9H-Purin-6-amine
9-(2-Deoxy-.beta.-D-erythro-pentofuranosyl)adenine
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine
adenine-9 2-deoxy-beta-delta-erythro-Pentofuranoside
9-(2-deoxy-beta-delta-ribofuranosyl)-9H-Purin-6-amine
1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-b-D-Ribofuranose
9-(2-deoxy-b-D-erythro-pentofuranosyl)-9H-Purin-6-amine
1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-Ribofuranose
9-(2-deoxy-beta-D-erythro-pentofuranosyl)-9H-Purin-6-amine
1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-Ribofuranose
9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-9H-Purin-6-amine
.beta.-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-
2'-DEOXYADENOSINE (USP IMPURITY)
5-(6-AMINO-PURIN-9-YL)-2-HYDROXYMETHYL-TETRAHYDRO-FURAN-3-OL
9H-Purin-6-amine, 9-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-
NSC83258
Adenosine, 2'deoxy
2'-DEOXYADENOSINE [INCI]
DTXCID701023135
9HPurin6amine, 9(2deoxybetaDribofuranosyl)
betaDerythroPentofuranoside, adenine9 2deoxy
9HPurin6amine, 9(2deoxybetaDerythropentofuranosyl)
betaDRibofuranose, 1(6amino9Hpurin9yl)1,2dideoxy
213-488-7
683-408-7
Adenine deoxyribonucleoside
Adenosine, 2'-deoxy,
MFCD00005754
Adenine deoxyriboside
2'-dA
desoxyadenosin
2'-Deoxyformycin A
9-(2-Deoxy-|A-D-threo-pentofuranosyl)-9H-purin-6-amine
(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
(2r,3s,5r)-5-(6-Amino-9h-Purin-9-Yl)-Tetrahydro-2-(Hydroxymethyl)furan-3-Ol
3D1
2'-deoxy-d-adenosine
9-(2-Deoxy-beta-D-ribofuranosyl)adenine
UNII-P582C98ULC
DNA nucleoside A
2''''-Deoxyadenosine
2'-Deoxyadenosine Anhydrous
2-Deoxyadenosine monohydrate
SCHEMBL19877
2'-Deoxyadenosine (Standard)
CHEMBL449329
GTPL5109
ACon0_001347
BCP11997
HY-W040329R
BDBM50453912
AKOS015896793
9-(2-Deoxy-b-D-ribofuranosyl)adenine
CS-W021069
HY-W040329
(R)-1-C-(7-Amino-1H-pyrazolo(4,3-d)pyrimidin-3-yl)-1,4-anhydro-2-deoxy-D-erythro-pentitol
2'-Deoxyadenosine - isolated from DNA
2'-Deoxyadenosine monohydrate, >=99%
NCGC00161970-01
40627-14-3
AS-14314
FD158139
2 inverted exclamation marka-Deoxyadenosine
HY-154058
CS-0674964
D0046
NS00014680
Adenosine, 2'-deoxy- (6CI,7CI,8CI,9CI)
C00559
EN300-108104
Q422457
9-(2'-Deoxy-.beta.-D-erythro-pentofuranosyl)adenine
Z1416201984
D2DF2A54-B4A8-4727-A05C-3D1123687898
2'-Deoxyadenosine monohydrate, powder, BioReagent, suitable for cell culture
663188-78-1
D-erythro-Pentitol, 1-C-(7-amino-1H-pyrazolo(4,3-d)pyrimidin-3-yl)-1,4-anhydro-2-deoxy-, (R)-