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Compound Detail

CHEMBL420705

(S)-PIA
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C[C@@H](Cc1ccccc1)Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL420705
Name (S)-PIA
Phase Preclinical
Structure Type MOL
InChI Key RIRGCFBBHQEQQH-KFAHYOAQSA-N
10
Targets
28
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

385.4
MW (Da)
0.48
ALogP
9
HBA
4
HBD
125.5
PSA (Ų)
0.48
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H23N5O4
MW 385.42
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness 0.52

Activity Summary

Ki 25 meas. best 8.1
IC50 2 meas. best 6.98
EC50 1 meas. best 6.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A1
CHEMBL4975
 Ki 8.1 7.9833 8.0 3
Adenosine receptor A1
CHEMBL318
 Ki 7.96 7.3167 11.0 6
Adenosine receptor
CHEMBL2111386
 Ki 7.82 7.006 15.0 5
Adenosine receptor A3
CHEMBL256
 Ki 7.17 7.17 68.0 1
Adenosine receptor A1
CHEMBL318
 IC50 6.98 6.98 105.0 1
Adenosine receptor A2a
CHEMBL2605
 Ki 6.89 6.89 130.0 1
Adenosine receptor A3
CHEMBL256
 EC50 6.68 6.68 210.0 1
Adenosine receptor A3
CHEMBL3360
 Ki 6.62 6.62 240.0 3
Adenosine A2 receptor
CHEMBL2094117
 Ki 5.76 5.1667 1720.0 3
Adenosine receptor A2a
CHEMBL251
 Ki 5.75 5.75 1800.0 2
Adenosine receptor A2a
CHEMBL302
 Ki 5.52 5.52 3000.0 1
Unchecked
CHEMBL612545
 IC50 5.38 5.38 4200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A1 Ki = 8.0 nM 8.1 Antagonist binding of N6-cyclohexyl-[3H]-adenosine to bovine brain 6279840
Adenosine receptor A1 Ki = 11.0 nM 7.96 Inhibition of [3H]CHA (N6-cyclohexyl adenosine) to rat brain membrane Adenosine ... 11881988
Adenosine receptor A1 Ki = 11.7 nM 7.93 Inhibitory activity at Adenosine A1 receptor by inhibition of [3H]CHA binding to... 9572897
Adenosine receptor A1 Ki = 12.0 nM 7.92 Ability to displace the specific binding of [3H]CHA to adenosine A1 receptor fro... 10956189
Adenosine receptor Ki = 15.0 nM 7.82 Antagonist binding of 2-chloro-[3H]-adenosine to rat brain 6279840
Adenosine receptor A1 Ki = 47.6 nM 7.32 Displacement of [3H]CHA from adenosine A1 receptor of rat whole brain 2995663
Adenosine receptor A1 Ki = 49.0 nM 7.31 Binding affinity to adenosine A1 receptor in rat whole brain membranes by [3H]N6... 2888894
Adenosine receptor A1 Ki = 49.3 nM 7.31 Binding affinity for Adenosine A1 receptor in cerebral cortices of Sprague-Dawle... 2374150
Adenosine receptor Ki = 50.0 nM 7.3 Antagonist binding of L-N6-phenyl-isopropyl)-[3H]adenosine to rat fat 6279840
Adenosine receptor A1 Ki = 50.0 nM 7.3 Inhibition of [3H]- (R)-P1A binding to adenosine A1 receptor 1766003
Adenosine receptor A3 Ki = 68.0 nM 7.17 Affinity for human Adenosine A3 receptor expressed in CHO cell 12238926
Adenosine receptor A1 IC50 = 105.0 nM 6.98 Evaluated for the binding affinity towards the Adenosine A1 receptor in cerebral... 2374150
Adenosine receptor Ki = 110.0 nM 6.96 Antagonist binding of N6-cyclohexyl-[3H]-adenosine to rat testes 6279840
Adenosine receptor Ki = 125.0 nM 6.9 Antagonist binding of N6-cyclohexyl-[3H]-adenosine to rat brain 6279840
Adenosine receptor A2a Ki = 130.0 nM 6.89 Antagonist binding of N6-cyclohexyl-[3H]-adenosine to guinea pig brain 6279840
Adenosine receptor A1 Ki = 200.0 nM 6.7 Evaluated for the binding affinity towards the Adenosine A1 receptor in corpora ... 2374150
Adenosine receptor A3 EC50 = 210.0 nM 6.68 Effect on forskolin-stimulated cyclic AMP production in intact chinese hamster o... 12238926
Adenosine receptor A3 Ki = 241.0 nM 6.62 Inhibitory activity against Adenosine A3 receptor by inhibiting specific [3H](R)... 9572897
Adenosine receptor A3 Ki = 240.0 nM 6.62 Affinity to Adenosine A3 receptor of rat testis membrane using [3H](R)-PIA with ... 11881988
Adenosine receptor A3 Ki = 241.0 nM 6.62 Ability to displace the specific binding of [3H](R)-PIA to adenosine A3 receptor... 10956189

Literature References

PubMed DOI Target Context # Activities
6279840 10.1021/jm00345a001 Adenosine receptor 6
2374150 10.1021/jm00170a031 Adenosine receptor A1 3
10956189 10.1021/jm990321p Unchecked 3
12238926 10.1021/jm020211+ Adenosine receptor A3 3
9572897 10.1021/jm9707737 Unchecked 3
2888894 10.1021/jm00393a003 Mus musculus 2
6279840 10.1021/jm00345a001 Adenosine receptor A1 2
9572897 10.1021/jm9707737 Adenosine receptor A2a 1
11881988 10.1021/jm0102755 Adenosine receptors; A1 & A3 1
11881988 10.1021/jm0102755 Adenosine receptors; A1 & A2a 1
11881988 10.1021/jm0102755 Adenosine receptor A3 1
11881988 10.1021/jm0102755 Adenosine receptor A2a 1
11881988 10.1021/jm0102755 Adenosine receptor A1 1
9572897 10.1021/jm9707737 Adenosine receptor A3 1
2888894 10.1021/jm00393a003 Adenosine receptor A1 1
9572897 10.1021/jm9707737 Adenosine receptor A1 1
2999397 10.1021/jm00149a016 Alpha-1A adrenergic receptor 1
2999397 10.1021/jm00149a016 ADMET 1
6279840 10.1021/jm00345a001 Adenosine receptor A2a 1
6279840 10.1021/jm00345a001 Adenosine A2 receptor 1

Data from ChEMBL 36 via Core Engine