piclidenoson   

GtoPdb Ligand ID: 422

Abbreviated name: IB-MECA
Synonyms: CF 101 | CF101 | N(6)-ibamu
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].
2D Structure
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Physico-chemical Properties
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
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
Classification
Compound class Synthetic organic
IUPAC Name
(2S,3S,4R,5R)-3,4-dihydroxy-5-[6-[(3-iodophenyl)methylamino]purin-9-yl]-N-methyloxolane-2-carboxamide
International Nonproprietary Names
INN number INN
10136 piclidenoson
Synonyms
CF 101 | CF101 | N(6)-ibamu
Database Links
BindingDB Ligand 50118812
CAS Registry No. 152918-18-8 (source: Scifinder)
ChEBI CHEBI:73286
ChEMBL Ligand CHEMBL119709
GtoPdb PubChem SID 135650362
PubChem CID 123683
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Tocris
IB-MECA
Cat. No. 1066