2-chloroadenosine   Click here for help

GtoPdb Ligand ID: 372

Synonyms: 2Cl-Ado | CADO
Compound class: Synthetic organic
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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

2-chloroadenosine 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 301.06
XLogP -0.71
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)n1cnc2c1nc(Cl)nc2N
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2N
InChI InChI=1S/C10H12ClN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1
InChI Key BIXYYZIIJIXVFW-UUOKFMHZSA-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
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Why are A(2B) receptors low-affinity adenosine receptors? Mutation of Asn273 to Tyr increases affinity of human A(2B) receptor for 2-(1-Hexynyl)adenosine.
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2. Bruns RF. (1980)
Adenosine receptor activation in human fibroblasts: nucleoside agonists and antagonists.
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Structure-activity relationships for 2-substituted adenosines at A1 and A2 adenosine receptors.
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Species difference in the G protein selectivity of the human and bovine A1-adenosine receptor.
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Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.
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Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors.
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7. Linden J, Thai T, Figler H, Jin X, Robeva AS. (1999)
Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells.
Mol Pharmacol, 56 (4): 705-13. [PMID:10496952]
8. Rivkees SA, Barbhaiya H, IJzerman AP. (1999)
Identification of the adenine binding site of the human A1 adenosine receptor.
J Biol Chem, 274 (6): 3617-21. [PMID:9920910]
9. van Galen PJ, van Bergen AH, Gallo-Rodriguez C, Melman N, Olah ME, IJzerman AP, Stiles GL, Jacobson KA. (1994)
A binding site model and structure-activity relationships for the rat A3 adenosine receptor.
Mol Pharmacol, 45 (6): 1101-11. [PMID:8022403]