piclidenoson   Click here for help

GtoPdb Ligand ID: 422

Abbreviated name: IB-MECA
Synonyms: CF 101 | CF101 | N(6)-ibamu
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].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
A3 receptor Hs Agonist Full agonist 8.7 – 9.2 pKi - 4,7,10,13
pKi 8.7 – 9.2 [4,7,10,13]
A1 receptor Hs Agonist Agonist 7.3 pKi - 8
pKi 7.3 (Ki 5.1x10-8 M) [8]
A2A receptor Hs Agonist Full agonist 5.6 – 6.3 pKi - 8-10
pKi 5.6 – 6.3 [8-10]
A2B receptor Hs Agonist Full agonist 4.3 – 4.9 pKi - 8,11
pKi 4.3 – 4.9 [8,11]