regadenoson   Click here for help

GtoPdb Ligand ID: 5596

Synonyms: CVT-3146 | Lexiscan® | Rapiscan®
Approved drug
regadenoson is an approved drug (FDA (2008), EMA (2010))
Compound class: Synthetic organic
Comment: Regadenoson is a selective adenosine A2A receptor agonist, with a substantially longer biological half-life than adenosine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 5
Rotatable bonds 5
Topological polar surface area 185.94
Molecular weight 390.14
XLogP -1.23
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OCC1OC(C(C1O)O)n1cnc2c1nc(nc2N)n1ncc(c1)C(=O)NC
Isomeric SMILES OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(nc2N)n1ncc(c1)C(=O)NC
InChI InChI=1S/C15H18N8O5/c1-17-13(27)6-2-19-23(3-6)15-20-11(16)8-12(21-15)22(5-18-8)14-10(26)9(25)7(4-24)28-14/h2-3,5,7,9-10,14,24-26H,4H2,1H3,(H,17,27)(H2,16,20,21)/t7-,9-,10-,14-/m1/s1
InChI Key LZPZPHGJDAGEJZ-AKAIJSEGSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
A2A receptor Primary target of this compound Hs Agonist Agonist 6.5 pKi - 1
pKi 6.5 (Ki 2.9x10-7 M) [1]
A1 receptor Hs Agonist Agonist <5.0 pKi - 1
pKi <5.0 (Ki >1x10-5 M) [1]
A2B receptor Hs Agonist Agonist <5.0 pKi - 1
pKi <5.0 (Ki >1x10-5 M) [1]
A3 receptor Hs Agonist Agonist <5.0 pKi - 1
pKi <5.0 (Ki >1x10-5 M) [1]