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adenosine
Sign in to saveAlso known as Adenocard®, 9-beta-D-ribofuranosyl-9H-purin-6-amine, Ade-Rib, Ado, Adenosin, (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol, beta-D-Adenosine, 9-beta-D-Ribofuranosidoadenine
Adenosine (symbol A) is an organic compound that occurs widely in nature in the form of diverse derivatives. The molecule consists of an adenine attached to a ribose via a β-N9-glycosidic bond. Adenosine is one of the four nucleoside building blocks of RNA (and its derivative deoxyadenosine is a building block of DNA), which are essential for all life on Earth. Its derivatives include the energy carriers adenosine mono-, di-, and triphosphate, also known as AMP/ADP/ATP. Cyclic adenosine monophosphate (cAMP) is pervasive in signal transduction. Adenosine is used as an intravenous medication for
OverviewAI-generated
Adenosine is a chemical compound with the formula C₁₀H₁₃N₅O₄. Its IUPAC name is (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol. The substance has a mass of 267.097 and a weight of 267.24. It exhibits a melting point of 235.5 and a pKa of 12.4. The defined daily dose is 15, and its solubility is 5.1.
Chemical properties include an xlogp of -1.1 and a tpsa of 140. The molecule contains 4 hydrogen bond donors and 8 hydrogen bond acceptors, with a charge of 0. Adenosine is referenced by 859 other encyclopedia articles.
Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C10H13N5O4
- Molecular weight
- 267.24 g/mol
- IUPAC name
- (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- SMILES
- C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
- InChIKey
- OIRDTQYFTABQOQ-KQYNXXCUSA-N
- XLogP
- -1.1
- Polar surface area
- 140 Ų
- H-bond donors
- 4
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
326,381 papers- Adenosine in Interventional Cardiology: Physiopathologic and Pharmacologic Effects in Coronary Artery Disease.ReviewInternational journal of molecular sciences · 2024Marchi E, Muraca I, Berteotti M et al.DOI: 10.3390/ijms25115852
- Adenosine kinase and ADAL coordinate detoxification of modified adenosines to safeguard metabolism.Cell · 2025Ogawa A, Watanabe S, Ozerova I et al.DOI: 10.1016/j.cell.2025.07.041
- Adenosine as a Key Mediator of Neuronal Survival in Cerebral Ischemic Injury.ReviewNeurochemical research · 2022Khan H, Kaur P, Singh TG et al.DOI: 10.1007/s11064-022-03737-3
- Adenosine-associated delivery systems.ReviewJournal of drug targeting · 2015Kazemzadeh-Narbat M, Annabi N, Tamayol A et al.DOI: 10.3109/1061186X.2015.1058803
- Adenosine: The common target between cancer immunotherapy and glaucoma in the eye.ReviewLife sciences · 2021Hallaj S, Mirza-Aghazadeh-Attari M, Arasteh A et al.DOI: 10.1016/j.lfs.2021.119796
- The adenosine-mediated, neuronal-glial, homeostatic sleep response.ReviewCurrent opinion in neurobiology · 2017Greene RW, Bjorness TE, Suzuki ADOI: 10.1016/j.conb.2017.05.015
- Adenosine-assisted embolization of cerebral arteriovenous malformations: a systematic review and meta-analysis.Journal of neurointerventional surgery · 2025Bocanegra-Becerra JE, Andreão FF, Acha Sánchez JL et al.DOI: 10.1136/jnis-2024-021866
- Adenosine as an antiarrhythmic agent.ReviewThe American journal of cardiology · 1997Wilbur SL, Marchlinski FEDOI: 10.1016/s0002-9149(97)00261-0
via PubMed
~14 min read
Encyclopedic overview
21 sectionsContents
- Medical uses
- Supraventricular tachycardia
- Nuclear stress test
- Dosage
- Adverse effects
- Drug interactions
- Contraindications
- Pharmacological effects
- Adenosine receptors
- Ghrelin/growth hormone secretagogue receptor
- Mechanism of action
- Metabolism
- Research
- Viruses
- Anti-inflammatory properties
- Central nervous system
- Hair
- Sleep
- Vasodilation
- See also
- References
Adenosine (symbol A) is an organic compound that occurs widely in nature in the form of diverse derivatives. The molecule consists of an adenine attached to a ribose via a β-N9-glycosidic bond. Adenosine is one of the four nucleoside building blocks of RNA (and its derivative deoxyadenosine is a building block of DNA), which are essential for all life on Earth. Its derivatives include the energy carriers adenosine mono-, di-, and triphosphate, also known as AMP/ADP/ATP. Cyclic adenosine monophosphate (cAMP) is pervasive in signal transduction. Adenosine is used as an intravenous medication for some cardiac arrhythmias.
Adenosyl (abbreviated Ado or '''5'-dAdo''') is the chemical group formed by removal of the 5′-hydroxy (OH) group. It is found in adenosylcobalamin (an active form of vitamin B12) and as a radical in the radical SAM enzymes.
Excerpted from Wikipedia’s “adenosine” article, available under the CC BY-SA 4.0 licence.