apadenoson   Click here for help

GtoPdb Ligand ID: 3290

Synonyms: ATL-146e | BMS-068645
Compound class: Synthetic organic
Comment: There is some ambiguity in the literature and on other online resources as to the stereochemistry of apadenoson, therefore representations elsewhere may vary slightly from the structure shown here. Our structure is the same as that specified in [1], while the compound is shown on PubChem with CID 9805430.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 174.71
Molecular weight 486.22
XLogP 2.22
No. Lipinski's rules broken 1
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Canonical SMILES CCNC(=O)C1OC(C(C1O)O)n1cnc2c1nc(C#CCC1CCC(CC1)C(=O)OC)nc2N
Isomeric SMILES CCNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(C#CC[C@@H]1CC[C@H](CC1)C(=O)OC)nc2N
InChI InChI=1S/C23H30N6O6/c1-3-25-21(32)18-16(30)17(31)22(35-18)29-11-26-15-19(24)27-14(28-20(15)29)6-4-5-12-7-9-13(10-8-12)23(33)34-2/h11-13,16-18,22,30-31H,3,5,7-10H2,1-2H3,(H,25,32)(H2,24,27,28)/t12-,13-,16-,17+,18-,22+/m0/s1
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
A2A receptor Hs Agonist Agonist 9.3 pKi - 2
pKi 9.3 (Ki 5x10-10 M) [2]
A3 receptor Hs Agonist Agonist 7.3 pKi - 1
pKi 7.3 (Ki 4.5x10-8 M) [1]
A1 receptor Hs Agonist Agonist 7.1 pKi - 1
pKi 7.1 (Ki 7.7x10-8 M) [1]