piclidenoson   Click here for help

GtoPdb Ligand ID: 422

Abbreviated name: IB-MECA
Synonyms: CF 101 | CF101 | N(6)-ibamu
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Piclidenoson is a selective agonist of the adenosine A3 receptor. It has anti-inflammatory action which is being investigated for translation to the clinic [2].
Early investigations revealed anti-cancer effects [1,5,12].
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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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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 9
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 134.42
Molecular weight 510.05
XLogP 2.2
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 CNC(=O)C1OC(C(C1O)O)n1cnc2c1ncnc2NCc1cccc(c1)I
Isomeric SMILES CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1cccc(c1)I
InChI InChI=1S/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1
InChI Key HUJXGQILHAUCCV-MOROJQBDSA-N
References
1. Bar-Yehuda S, Madi L, Silberman D, Gery S, Shkapenuk M, Fishman P. (2005)
CF101, an agonist to the A3 adenosine receptor, enhances the chemotherapeutic effect of 5-fluorouracil in a colon carcinoma murine model.
Neoplasia, 7 (1): 85-90. [PMID:15720820]
2. Borea PA, Gessi S, Bar-Yehuda S, Fishman P. (2009)
A3 adenosine receptor: pharmacology and role in disease.
Handb Exp Pharmacol, (193): 297-327. [PMID:19639286]
3. David M, Akerman L, Ziv M, Kadurina M, Gospodinov D, Pavlotsky F, Yankova R, Kouzeva V, Ramon M, Silverman MH et al.. (2012)
Treatment of plaque-type psoriasis with oral CF101: data from an exploratory randomized phase 2 clinical trial.
J Eur Acad Dermatol Venereol, 26 (3): 361-7. [PMID:21504485]
4. Feoktistov I, Garland EM, Goldstein AE, Zeng D, Belardinelli L, Wells JN, Biaggioni I. (2001)
Inhibition of human mast cell activation with the novel selective adenosine A(2B) receptor antagonist 3-isobutyl-8-pyrrolidinoxanthine (IPDX)(2).
Biochem Pharmacol, 62 (9): 1163-73. [PMID:11705449]
5. Fishman P, Bar-Yehuda S, Ohana G, Barer F, Ochaion A, Erlanger A, Madi L. (2004)
An agonist to the A3 adenosine receptor inhibits colon carcinoma growth in mice via modulation of GSK-3 beta and NF-kappa B.
Oncogene, 23 (14): 2465-71. [PMID:14691449]
6. Fishman P, Cohen S, Bar-Yehuda S. (2013)
Targeting the A3 adenosine receptor for glaucoma treatment (review).
Mol Med Rep, 7 (6): 1723-5. [PMID:23563604]
7. Gallo-Rodriguez C, Ji XD, Melman N, Siegman BD, Sanders LH, Orlina J, Fischer B, Pu Q, Olah ME, van Galen PJ et al.. (1994)
Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.
J Med Chem, 37 (5): 636-46. [PMID:8126704]
8. Jacobson KA, Gao ZG. (2006)
Adenosine receptors as therapeutic targets.
Nat Rev Drug Discov, 5 (3): 247-64. [PMID:16518376]
9. Kim J, Wess J, van Rhee AM, Schöneberg T, Jacobson KA. (1995)
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.
J Biol Chem, 270 (23): 13987-97. [PMID:7775460]
10. Klotz KN, Hessling J, Hegler J, Owman C, Kull B, Fredholm BB, Lohse MJ. (1998)
Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells.
Naunyn Schmiedebergs Arch Pharmacol, 357 (1): 1-9. [PMID:9459566]
11. 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]
12. Ohana G, Bar-Yehuda S, Arich A, Madi L, Dreznick Z, Rath-Wolfson L, Silberman D, Slosman G, Fishman P. (2003)
Inhibition of primary colon carcinoma growth and liver metastasis by the A3 adenosine receptor agonist CF101.
Br J Cancer, 89 (8): 1552-8. [PMID:14562031]
13. Varani K, Merighi S, Gessi S, Klotz KN, Leung E, Baraldi PG, Cacciari B, Romagnoli R, Spalluto G, Borea PA. (2000)
[(3)H]MRE 3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A(3) adenosine receptors.
Mol Pharmacol, 57 (5): 968-75. [PMID:10779381]
14. Varani K, Padovan M, Govoni M, Vincenzi F, Trotta F, Borea PA. (2010)
The role of adenosine receptors in rheumatoid arthritis.
Autoimmun Rev, 10 (2): 61-4. [PMID:20691813]