compound 4g [PMID: 22220592]   Click here for help

GtoPdb Ligand ID: 9236

Synonyms: Example XCII [US20160175314]
PDB Ligand
Compound class: Synthetic organic
Comment: Compound 4g [PMID: 22220592]) is a potent, efficient, selective, and orally active 1,2,4-triazine derivative ligand. Heptares identified this compound using structure-based drug design approaches to discover antagonists of the adenosine A2A receptor [1,3]. The X-ray crystal structure of 4g locates it inside the receptor's orthosteric binding cavity [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 77.58
Molecular weight 277.13
XLogP 2.25
No. Lipinski's rules broken 0
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Canonical SMILES Nc1nnc(c(n1)c1ccccc1)c1cc(C)nc(c1)C
Isomeric SMILES Nc1nnc(c(n1)c1ccccc1)c1cc(C)nc(c1)C
InChI InChI=1S/C16H15N5/c1-10-8-13(9-11(2)18-10)15-14(19-16(17)21-20-15)12-6-4-3-5-7-12/h3-9H,1-2H3,(H2,17,19,21)
Bioactivity Comments
In addition to the Ki, a Kd of 1.26 nM was recorded with Surface Plasmon Resonance. Overall, the derivatives had A3 receptor antagonist affinity of >10μM and generally 10-fold selectivity over A2B [2].
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 8.1 pKi - 2
pKi 8.1 (Ki 7.76x10-9 M) [2]