adenosine   Click here for help

GtoPdb Ligand ID: 2844

Synonyms: Adenocard® | Adenoscan®
Approved drug PDB Ligand
adenosine is an approved drug (FDA (1989))
Compound class: Metabolite
Comment: Endogenous nucleoside, a component of nucleic acids and an important neurotransmitter.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: adenosine

adenosine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 139.54
Molecular weight 267.1
XLogP -1.42
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OCC1OC(C(C1O)O)n1cnc2c1ncnc2N
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
InChI InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChI Key OIRDTQYFTABQOQ-KQYNXXCUSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Baldwin SA, Yao SY, Hyde RJ, Ng AM, Foppolo S, Barnes K, Ritzel MW, Cass CE, Young JD. (2005)
Functional characterization of novel human and mouse equilibrative nucleoside transporters (hENT3 and mENT3) located in intracellular membranes.
J Biol Chem, 280 (16): 15880-7. [PMID:15701636]
2. Fredholm BB. (1995)
Astra Award Lecture. Adenosine, adenosine receptors and the actions of caffeine.
Pharmacol Toxicol, 76 (2): 93-101. [PMID:7746802]
3. Fredholm BB, Chen JF, Masino SA, Vaugeois JM. (2005)
Actions of adenosine at its receptors in the CNS: insights from knockouts and drugs.
Annu Rev Pharmacol Toxicol, 45: 385-412. [PMID:15822182]
4. Tai AW, Bojjireddy N, Balla T. (2011)
A homogeneous and nonisotopic assay for phosphatidylinositol 4-kinases.
Anal Biochem, 417 (1): 97-102. [PMID:21704602]
5. Yan L, Burbiel JC, Maass A, Müller CE. (2003)
Adenosine receptor agonists: from basic medicinal chemistry to clinical development.
Expert Opin Emerg Drugs, 8 (2): 537-76. [PMID:14662005]
6. Yao SY, Ng AM, Cass CE, Baldwin SA, Young JD. (2011)
Nucleobase transport by human equilibrative nucleoside transporter 1 (hENT1).
J Biol Chem, 286 (37): 32552-62. [PMID:21795683]
7. Zhou M, Duan H, Engel K, Xia L, Wang J. (2010)
Adenosine transport by plasma membrane monoamine transporter: reinvestigation and comparison with organic cations.
Drug Metab Dispos, 38 (10): 1798-805. [PMID:20592246]