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Adenosin
Sign in to saveAlso known as Adenocard®, 9-beta-D-ribofuranosyl-9H-purin-6-amine, Ade-Rib, Ado, (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol, beta-D-Adenosine, 9-beta-D-Ribofuranosidoadenine
Nukleosid, organische Verbindung
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
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1989
- Admin. routes
- parenteral
- Indications
- pain, neoplasm, myocardial infarction, cardiovascular disease
via ChEMBL · EBI
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
Wikidata facts
- Has part
- carbon
- Mass
- 267.097
- Manufacturer
- Pfizer
- Has use
- medication
Show 11 more facts
- chemical formula
- C₁₀H₁₃N₅O₄
- Commons category
- Adenosine
- medical condition treated
- Wolff–Parkinson–White syndrome
- canonical SMILES
- C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)CO)O)O
- isomeric SMILES
- C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
- defined daily dose
- 15
- subject has role
- primary metabolite
- melting point
- 235
- pKa
- 12.4
- solubility
- 5.1
- has characteristic
- bitterness
Sources (9)
via Wikidata · CC0
Article · Deutsch
Adenosin (A, Ado) ist ein Nukleosid und besteht aus der Nukleinbase Adenin und dem Zucker β-D-Ribose. Das Analogon mit Desoxyribose ist das Desoxyadenosin. Es ist Bestandteil der energiereichen Verbindungen ATP, ADP, AMP, der Ribonukleinsäure (RNA), verschiedenen Cofaktoren (z. B. Coenzym A, NADPH, NADH) und auch in einem Neuromodulator.
Abstract from DBpedia / Wikipedia · CC BY-SA