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Compound Detail

CHEMBL139000

(R)-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 CHEMBL139000
Name (R)-PIA
Phase Preclinical
Structure Type MOL
InChI Key RIRGCFBBHQEQQH-SSFGXONLSA-N
14
Targets
68
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 54 meas. best 9.6
IC50 9 meas. best 9.4
EC50 5 meas. best 7.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A1
CHEMBL4975
 Ki 9.6 8.824 0.2 5
Unchecked
CHEMBL612545
 IC50 9.4 7.705 0.4 2
Adenosine receptor
CHEMBL2111386
 Ki 9.22 8.562 0.6 5
Adenosine receptor A1
CHEMBL318
 Ki 9.22 8.63 0.6 18
Adenosine receptor A1
CHEMBL226
 Ki 8.7 7.9033 2.0 3
Adenosine receptor A1
CHEMBL318
 IC50 8.62 8.1067 2.4 3
Adenosine receptor A2a
CHEMBL2605
 Ki 8.48 8.48 3.3 1
Adenosine receptor
CHEMBL2111386
 IC50 8.43 7.725 3.7 2
Adenosine receptor A3
CHEMBL256
 Ki 8.06 7.9733 8.7 3
Adenosine receptor A3
CHEMBL256
 EC50 7.57 7.57 27.0 1
Adenosine receptor A3
CHEMBL3360
 Ki 7.28 7.28 53.0 3
Adenosine receptor A2a
CHEMBL302
 Ki 6.93 6.89 117.0 2
Adenosine A2 receptor
CHEMBL2094117
 Ki 6.92 6.494 120.0 10
Cavia porcellus
CHEMBL369
 EC50 6.36 6.36 440.0 1
Adenosine A2 receptor
CHEMBL2094117
 IC50 6.28 6.28 530.0 1
Adenosine receptor A2a
CHEMBL251
 Ki 6.12 6.0967 750.0 3
Adenosine receptor A1
CHEMBL226
 IC50 6.08 6.08 830.0 1
Adenosine A2 receptor
CHEMBL2094257
 EC50 6.02 6.02 950.0 1
Adenosine receptor A1
CHEMBL226
 EC50 5.92 5.92 1200.0 1
Adenosine receptor A2b
CHEMBL255
 EC50 5.78 5.78 1680.0 1
Adenosine A2 receptor
CHEMBL2094257
 Ki 5.77 5.77 1700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A1 Ki = 0.25 nM 9.6 Antagonist binding of N6-cyclohexyl-[3H]-adenosine to bovine brain 6279840
Unchecked IC50 = 0.4 nM 9.4 In vitro inhibition of isoprenaline-stimulated cAMP accumulation in DDT1-MF2 cel... 10479279
Adenosine receptor A1 Ki = 0.6 nM 9.22 Ability to displace the specific binding of [3H]CHA to adenosine A1 receptor fro... 10956189
Adenosine receptor A1 Ki = 0.6 nM 9.22 Inhibition of [3H]CHA (N6-cyclohexyl adenosine) to rat brain membrane Adenosine ... 11881988
Adenosine receptor A1 Ki = 0.6 nM 9.22 Inhibitory activity at Adenosine A1 receptor by inhibition of [3H]CHA binding to... 9572897
Adenosine receptor Ki = 0.6 nM 9.22 Antagonist binding of 2-chloro-[3H]-adenosine to rat brain 6279840
Adenosine receptor A1 Ki = 1.0 nM 9.0 Binding affinity against high affinity component of adenosine A1 receptors from ... 1619615
Adenosine receptor A1 Ki = 1.1 nM 8.96 Binding affinity for adenosine A1 receptor in rat brain membranes using [3H]CHA ... 3005574
Adenosine receptor A1 Ki = 1.15 nM 8.94 Displacement of [3H]CHA from adenosine A1 receptor of rat whole brain 2995663
Adenosine receptor A1 Ki = 1.17 nM 8.93 Binding affinity for Adenosine A1 receptor in cerebral cortices of Sprague-Dawle... 2374150
Adenosine receptor A1 Ki = 1.17 nM 8.93 Inhibition of binding of [3H]N6-cyclohexyladenosine to adenosine A1 receptor of ... 2754691
Adenosine receptor A1 Ki = 1.2 nM 8.92 Binding affinity to adenosine A1 receptor in rat whole brain membranes by [3H]N6... 2888894
Adenosine receptor A1 Ki = 1.2 nM 8.92 Inhibition of [3H]- (R)-P1A binding to adenosine A1 receptor 1766003
Adenosine receptor A1 Ki = 1.2 nM 8.92 Binding affinity against adenosine A1 receptor using [3H]-CHA or [3H]PIA as radi... 1738138
Adenosine receptor A1 Ki = 1.2 nM 8.92 Binding affinity at adenosine A1 receptor from rat brain membranes by [3H]N6-cyc... 3385722
Adenosine receptor A1 Ki = 1.2 nM 8.92 Binding affinity towards adenosine A1 receptor on rat whole brain membrane using... 3336027
Adenosine receptor A1 Ki = 1.3 nM 8.89 Displacement of [3H]PIA from adenosine A1 receptor of rat brain membranes 3373486
Adenosine receptor A1 Ki = 1.3 nM 8.89 Binding affinity against adenosine A1 receptors from rat brain membranes using [... 1619615
Adenosine receptor Ki = 1.4 nM 8.85 Antagonist binding of N6-cyclohexyl-[3H]-adenosine to rat testes 6279840
Adenosine receptor Ki = 1.6 nM 8.8 Antagonist binding of N6-cyclohexyl-[3H]-adenosine to rat brain 6279840

Literature References

PubMed DOI Target Context # Activities
6279840 10.1021/jm00345a001 Adenosine receptor 6
3012086 10.1021/jm00156a016 Adenosine A2 receptor 5
10479279 10.1021/jm960682u Rattus norvegicus 5
2374150 10.1021/jm00170a031 Adenosine receptor A1 3
23403082 10.1016/j.bmcl.2013.01.025 Adenosine receptor A1 3
1619615 10.1021/jm00091a003 Adenosine receptor A1 3
10956189 10.1021/jm990321p Unchecked 3
9572897 10.1021/jm9707737 Unchecked 3
3373486 10.1021/jm00401a018 Adenosine receptor A1 3
12238926 10.1021/jm020211+ Adenosine receptor A3 3
3373486 10.1021/jm00401a018 Adenosine A2 receptor 3
11462973 10.1021/jm001054m Adenosine receptor A1 2
1875349 10.1021/jm00112a035 Rattus norvegicus 2
29939744 10.1021/acs.jmedchem.8b00435 Adenosine receptor A1 2
2888894 10.1021/jm00393a003 Mus musculus 2
3005574 10.1021/jm00153a008 Mus musculus 2
3005574 10.1021/jm00153a008 Rattus norvegicus 2
6279840 10.1021/jm00345a001 Adenosine receptor A1 2
7562934 10.1021/jm00020a014 Adenosine receptor A1 2
3336027 10.1021/jm00396a044 Adenosine receptor A1 2

Data from ChEMBL 36 via Core Engine