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Compound Detail

CHEMBL1095488

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Nc1nc(-c2ccccc2)c2c(n1)-c1cc(OCCN3CCOCC3)ccc1C2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1095488
Phase Preclinical
Structure Type MOL
InChI Key BCDASHXLAMCATI-UHFFFAOYSA-N
4
Targets
10
Activities
2
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

402.4
MW (Da)
2.65
ALogP
7
HBA
1
HBD
90.6
PSA (Ų)
0.55
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H22N4O3
MW 402.45
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -0.80

Activity Summary

Ki 8 meas. best 8.19
EC50 2 meas. best 7.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A2a
CHEMBL251
 Ki 8.19 8.1725 6.5 4
Adenosine receptor A1
CHEMBL226
 EC50 7.32 7.32 48.0 1
Adenosine receptor A1
CHEMBL226
 Ki 7.32 7.32 48.2 3
Adenosine receptor A2b
CHEMBL255
 EC50 6.64 6.64 230.0 1
Adenosine receptor A3
CHEMBL256
 Ki 6.37 6.37 430.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.0 mL.min-1.kg-1 Macaca fascicularis
CL 19.0 mL.min-1.kg-1 Rattus norvegicus
CL 97.0 mL.min-1.kg-1 Mus musculus
Cmax 4100.0 nM Rattus norvegicus
Cmax 4161.0 nM Rattus norvegicus
Cmax 2769.0 nM Macaca fascicularis
Cmax 1652.0 nM Rattus norvegicus
Cmax 1081.0 nM Mus musculus
F 55.0 % Macaca fascicularis
F 18.0 % Rattus norvegicus
F 61.0 % Mus musculus
T1/2 5.5 hr Macaca fascicularis
T1/2 1.2 hr Rattus norvegicus
T1/2 1.1 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A2a Ki = 6.5 nM 8.19 Antagonistic activity at adenosine A2A receptor 20338760
Adenosine receptor A2a Ki = 6.5 nM 8.19 Antagonist activity at human Adenosine receptor A2a assessed as inhibition of cA... 22239465
Adenosine receptor A2a Ki = 6.5 nM 8.19 Antagonist activity at human recombinant adenosine receptor A2a by cAMP assay 24164628
Adenosine receptor A2a Ki = 7.5 nM 8.12 Displacement of [3H]MSX-2 from human recombinant adenosine A2A receptor expresse... 34107215
Adenosine receptor A1 EC50 = 48.0 nM 7.32 Binding affinity to human recombinant adenosine A1 receptor expressed in CHO cel... 34107215
Adenosine receptor A1 Ki = 48.2 nM 7.32 Antagonistic activity at adenosine A1 receptor 20338760
Adenosine receptor A1 Ki = 48.2 nM 7.32 Antagonist activity at human Adenosine receptor A1 assessed as inhibition of cAM... 22239465
Adenosine receptor A1 Ki = 48.2 nM 7.32 Antagonist activity at human recombinant adenosine A1 receptor by cAMP assay 24164628
Adenosine receptor A2b EC50 = 230.0 nM 6.64 Binding affinity to human recombinant adenosine A2B receptor expressed in CHO ce... 34107215
Adenosine receptor A3 Ki = 430.0 nM 6.37 Displacement of [3H]PSB-11 from human recombinant adenosine A3 receptor expresse... 34107215

Literature References

PubMed DOI Target Context # Activities
22239465 10.1021/jm201640m Rattus norvegicus 12
22239465 10.1021/jm201640m Mus musculus 8
22239465 10.1021/jm201640m Cynomolgus monkey 4
22239465 10.1021/jm201640m Plasma 3
22239465 10.1021/jm201640m Adenosine receptor A2a 1
34107215 10.1021/acs.jmedchem.0c00914 Adenosine receptor A2b 1
34107215 10.1021/acs.jmedchem.0c00914 Adenosine receptor A1 1
34107215 10.1021/acs.jmedchem.0c00914 Adenosine receptor A3 1
34107215 10.1021/acs.jmedchem.0c00914 Adenosine receptor A2a 1
24164628 10.1021/jm4011669 Mus musculus 1
24164628 10.1021/jm4011669 Adenosine receptor A1 1
24164628 10.1021/jm4011669 Adenosine receptor A3 1
24164628 10.1021/jm4011669 Adenosine receptor A2a 1
24164628 10.1021/jm4011669 Adenosine receptor A2b 1
20338760 10.1016/j.bmcl.2010.03.024 Adenosine receptor A2a 1
22239465 10.1021/jm201640m Adenosine receptor A1 1
22239465 10.1021/jm201640m Brain 1
20338760 10.1016/j.bmcl.2010.03.024 Rattus norvegicus 1
20338760 10.1016/j.bmcl.2010.03.024 Mus musculus 1
20338760 10.1016/j.bmcl.2010.03.024 Adenosine receptor A1 1

Data from ChEMBL 36 via Core Engine