Structure via PubChem · Public domain (PubChem)
inosine
Sign in to saveAlso known as 9-beta-D-ribofuranosyl-9H-purin-6-ol, hypoxanthosine, hypoxanthine D-riboside, 9-beta-D-ribofuranosylhypoxanthine, i, 9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one, 9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3H-purin-6-one, 9-[(2R,3R,4R,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-3H-purin-6-one
Inosine is a nucleoside that is formed when hypoxanthine is attached to a ribose ring (also known as a ribofuranose) via a β-N9-glycosidic bond. It was discovered in 1965 in analysis of RNA transferase. Inosine is commonly found in tRNAs and is essential for proper translation of the genetic code in wobble base pairs. thumb|right|225px|Wobble base pairs for inosine and [[guanine]]
Chemical data
- Formula
- C10H12N4O5
- Molecular weight
- 268.23 g/mol
- IUPAC name
- 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
- SMILES
- C1=NC(=O)C2=C(N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
- InChIKey
- UGQMRVRMYYASKQ-KQYNXXCUSA-N
- XLogP
- -2.1
- Polar surface area
- 129 Ų
- H-bond donors
- 4
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- viral disease, melanoma, HIV infection, relapsing-remitting multiple sclerosis
via ChEMBL · EBI
Research
16,360 papers- Inosine in Biology and Disease.Genes · 2021
- Inosine, gut microbiota, and cancer immunometabolism.American journal of physiology. Endocrinology and metabolism · 2023
- Inosine in Neurodegenerative Diseases: From the Bench to the Bedside.Molecules (Basel, Switzerland) · 2022
- Inosine Triphosphate Pyrophosphatase (ITPase): Functions, Mutations, Polymorphisms and Its Impact on Cancer Therapies.Cells · 2022
- Recent Advances in Adenosine-to-Inosine RNA Editing in Cancer.Cancer treatment and research · 2023
via PubMed
Wikidata facts
Show 8 more facts
- found in taxon
- Streptomyces
- chemical formula
- C₁₀H₁₂N₄O₅
- canonical SMILES
- C1=NC(=O)C2=C(N1)N(C=N2)C3C(C(C(O3)CO)O)O
- isomeric SMILES
- C1=NC(=O)C2=C(N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
- World Health Organisation international non-proprietary name
- inosine
- Commons category
- Inosine
- has characteristic
- bitterness
- subject has role
- primary metabolite
via Wikidata · CC0
~5 min read
Encyclopedic overview
9 sectionsContents
- Reactions
- Clinical significance
- Binding
- Biotechnology
- Fitness
- Feeding stimulant
- See also
- References
- External links
Inosine is a nucleoside that is formed when hypoxanthine is attached to a ribose ring (also known as a ribofuranose) via a β-N9-glycosidic bond. It was discovered in 1965 in analysis of RNA transferase. Inosine is commonly found in tRNAs and is essential for proper translation of the genetic code in wobble base pairs. thumb|right|225px|Wobble base pairs for inosine and [[guanine]]
Knowledge of inosine metabolism has led to advances in immunotherapy in recent decades. Inosine monophosphate is oxidised by the enzyme inosine monophosphate dehydrogenase, yielding xanthosine monophosphate, a key precursor in purine metabolism. Mycophenolate mofetil is an anti-metabolite, anti-proliferative drug that acts as an inhibitor of inosine monophosphate dehydrogenase. It is used in the treatment of a variety of autoimmune diseases including granulomatosis with polyangiitis because the uptake of purine by actively dividing B cells can exceed 8 times that of normal body cells, and, therefore, this set of white cells (which cannot operate purine salvage pathways) is selectively targeted by the purine deficiency resulting from inosine monophosphate dehydrogenase (IMD) inhibition.
Excerpted from Wikipedia’s “inosine” article, available under the CC BY-SA 4.0 licence.