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 or derivative
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

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View more information in the IUPHAR Pharmacology Education Project: adenosine

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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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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 CDK toolkit. 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
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.

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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
Natural/Endogenous Targets
Target
A1 receptor
A2A receptor
A2B receptor
A3 receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
Ecto-5'-Nucleotidase
S-Adenosylhomocysteine hydrolase
Adenosine deaminase 3.5.4.4 Adenosine + H2O = inosine + NH3
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Sodium/nucleoside cotransporter 1
Sodium/nucleoside cotransporter 2
Solute carrier family 28 member 3
Equilibrative nucleoside transporter 1 6
Equilibrative nucleoside transporter 2
Equilibrative nucleoside transporter 3 1
Plasma membrane monoamine transporter 7
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
A1 receptor Ligand is endogenous in the given species Rn Agonist Agonist 7.1 pKi - 5
⤷ pKi 7.1 (Ki 7.3x10-8 M) [5]
A1 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist ~7.0 pKi - 5
⤷ pKi ~7.0 (Ki ~1x10-7 M) [5]
A2A receptor Rn Agonist Agonist 6.8 pKi - 5
⤷ pKi 6.8 (Ki 1.5x10-7 M) [5]
A3 receptor Ligand is endogenous in the given species Hs Agonist Agonist 6.5 pKi - 2-3,5
⤷ pKi 6.5 (Ki 2.9x10-7 M) [2-3,5]
A2A receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 6.5 pKi - 2-3,5
⤷ pKi 6.5 (Ki 3.1x10-7 M) [2-3,5]
A2B receptor Ligand is endogenous in the given species Rn Agonist Agonist 5.3 pKi - 5
⤷ pKi 5.3 (Ki 5.1x10-6 M) [5]
A3 receptor Ligand is endogenous in the given species Rn Agonist Agonist 5.2 pKi - 5
⤷ pKi 5.2 (Ki 6.5x10-6 M) [5]
A2B receptor Ligand is endogenous in the given species Hs Agonist Agonist 4.8 pKi - 2-3,5
⤷ pKi 4.8 (Ki 1.5x10-5 M) [2-3,5]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPM4 Hs Channel blocker - 3.2 pIC50 -
⤷ pIC50 3.2 (IC50 6.3x10-4 M)
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphatidylinositol 4-kinase type 2 alpha Hs Inhibitor Inhibition 4.5 – 5.0 pIC50 - 4
⤷ pIC50 4.5 – 5.0 [4]
phosphatidylinositol 4-kinase type 2 beta Hs Inhibitor Inhibition 4.5 – 5.0 pIC50 - 4
⤷ pIC50 4.5 – 5.0 [4]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Rank order of affinity at Adenosine deaminase 2'-deoxyadenosine > adenosine
Rank order of affinity at Adenosine kinase adenosine
Endogenous substrates in order of increasing Km: at Equilibrative nucleoside transporter 1 adenosine < inosine < uridine < guanosine < cytidine < hypoxanthine < adenine < thymine
Ligand mentioned in the following text fields
Adenosine receptors overview
Adenosine turnover overview
Adenylyl cyclases (ACs) overview
P2Y receptors overview