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Compound Detail

CHEMBL331372

CGS-21680
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CCNC(=O)[C@H]1O[C@@H](n2cnc3c(N)nc(NCCc4ccc(CCC(=O)O)cc4)nc32)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL331372
Name CGS-21680
Phase Preclinical
Structure Type MOL
InChI Key PAOANWZGLPPROA-RQXXJAGISA-N
15
Targets
104
Activities
4
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

499.5
MW (Da)
-0.16
ALogP
11
HBA
6
HBD
197.7
PSA (Ų)
0.22
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H29N7O6
MW 499.53
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness 0.06

Activity Summary

Ki 65 meas. best 8.06
EC50 18 meas. best 9.13
Kd 12 meas. best 8.37
IC50 9 meas. best 7.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine A2 receptor
CHEMBL2094257
 EC50 9.13 9.13 0.7 1
Adenosine receptor A2a
CHEMBL251
 EC50 8.85 7.57 1.4 5
Adenosine receptor A2a
CHEMBL251
 Kd 8.37 7.6117 4.3 12
Adenosine A2 receptor
CHEMBL2094117
 Ki 8.06 7.96 8.8 4
Adenosine receptor A3
CHEMBL256
 EC50 8.0 7.105 10.0 2
Adenosine receptor A2a
CHEMBL302
 Ki 7.96 7.8045 11.0 11
Adenosine receptor A2a
CHEMBL251
 Ki 7.9 7.394 12.5 15
Adenosine receptor A2a
CHEMBL251
 IC50 7.72 7.72 19.0 1
Adenosine receptor A2b
CHEMBL255
 EC50 7.4 7.4 39.8 1
Neutrophil
CHEMBL613710
 IC50 7.33 7.33 47.0 1
PBMC
CHEMBL613107
 IC50 7.24 7.16 58.0 2
Adenosine receptor A3
CHEMBL256
 Ki 7.17 6.769 67.0 10
Aorta
CHEMBL613606
 IC50 7.16 6.6567 69.2 3
Adenosine receptor A2a
CHEMBL302
 EC50 6.94 6.94 115.0 2
Adenosine receptor A1
CHEMBL226
 Ki 6.54 6.5075 289.0 8
Adenosine receptor A1
CHEMBL226
 EC50 6.3 5.745 501.2 2
Adenosine receptor A1
CHEMBL318
 Ki 6.25 5.7507 569.0 15
Adenosine receptor A3
CHEMBL3360
 Ki 6.23 6.23 584.0 2
Unchecked
CHEMBL612545
 IC50 5.9 5.9 1260.0 1
Rattus norvegicus
CHEMBL376
 IC50 4.75 4.75 18000.0 1
Adenosine receptor A1
CHEMBL2304404
 EC50 4.61 4.61 24547.1 1

Pharmacokinetic Data

Parameter Value Units Species
CL 82.0 mL.min-1.kg-1 Rattus norvegicus
CL 14.0 mL.min-1.kg-1 Rattus norvegicus
CL 8.0 mL.min-1.g-1 Homo sapiens
Cmax 271.0 nM Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine A2 receptor EC50 = 0.7413 nM 9.13 Coronary arteries vasodilation at the Adenosine A2 receptor in langendorff guine... 2016707
Adenosine receptor A2a EC50 = 1.413 nM 8.85 Partial agonist activity at human A2A receptor expressed in HEK293 cell membrane... 33764785
Adenosine receptor A2a EC50 = 2.12 nM 8.67 Agonist activity at human adenosine A2a receptor expressed in CHO cells assessed... 25221664
Adenosine receptor A2a Kd = 4.3 nM 8.37 Saturation binding of mutant human Adenosine A2A receptor (H250N) at pH 5.5 9258366
Adenosine receptor A2a Kd = 4.36 nM 8.36 Displacement of [3H]4-[2-[7-amino-2-(2-furyl)-1,2,4-triazolo[1,5-a][1,3,5]triazi... 25221664
Adenosine receptor A2a Kd = 7.6 nM 8.12 Saturation binding of human Adenosine A2A receptor (H250N) at pH 6.8 9258366
Adenosine receptor A2a Kd = 7.6 nM 8.12 Kd in saturation experiments using [3H]CGS-21680 at H250N mutant receptor in COS... 9258366
Adenosine A2 receptor Ki = 8.8 nM 8.06 Binding affinity against adenosine A2 receptor in rat striatal membranes using [... 1732541
Adenosine A2 receptor Ki = 8.8 nM 8.06 Inhibition of [3H]NECA binding to adenosine A2 receptor from rat striatal membra... 1613750
Adenosine receptor A3 EC50 = 10.0 nM 8.0 Agonist activity at human adenosine A3 receptor expressed in FlpIn-CHO cells ass... -
Adenosine A2 receptor Ki = 10.0 nM 8.0 Binding affinity against adenosine A2 receptor from rat striatum using [3H]NECA ... 1495019
Adenosine receptor A2a Ki = 11.0 nM 7.96 Binding affinity against adenosine A2a receptor from rat striatum using [3H]-CGS... 7739005
Adenosine receptor A2a Ki = 11.0 nM 7.96 Displacement of [3H]-CGS- 21680 from adenosine A2A receptor of rat striatal tiss... 10479279
Adenosine receptor A2a Ki = 11.0 nM 7.96 Displacement of [3H]-CGS- 21680 from Adenosine A2A receptor of rat striatum 7658444
Adenosine receptor A2a Kd = 11.6 nM 7.94 Saturation binding of human Adenosine A2A receptor H250N at pH 7.5 9258366
Adenosine receptor A2a Ki = 12.48 nM 7.9 Displacement of [3H]CGS21680 from human adenosine A2A receptor expressed in CHO ... 25780876
Adenosine receptor A2a EC50 = 12.59 nM 7.9 Agonist activity at human adenosine A2A receptor expressed in FlpIn-CHO cells as... -
Adenosine receptor A2a Ki = 15.0 nM 7.82 Tested for the binding affinity of A2a receptor by displacing the [3H]-CGS- 2168... 7932588
Adenosine receptor A2a Ki = 15.0 nM 7.82 Ability to displace radioligand [3H]- CGS 21680 from adenosine A2A receptor on r... 10212124
Adenosine receptor A2a Ki = 15.0 nM 7.82 Displacement of [3H]NECA from Adenosine A2A receptor in rat striatal membrane 11784146

Literature References

PubMed DOI Target Context # Activities
9258366 10.1021/jm970084v Adenosine receptor A2a 22
18045744 10.1016/j.ejmech.2007.10.021 Aorta 5
26756468 10.1021/acs.jmedchem.5b01402 Adenosine receptor A2b 4
26756468 10.1021/acs.jmedchem.5b01402 Adenosine receptor A2a 4
26756468 10.1021/acs.jmedchem.5b01402 Adenosine receptor A1 4
25221664 10.1021/ml5002486 Adenosine receptor A2a 4
- 10.6019/CHEMBL3301361 ADMET 3
18243699 10.1016/j.bmcl.2008.01.033 Rattus norvegicus 3
7739005 10.1021/jm00009a007 Adenosine receptor A2a 3
7658444 10.1021/jm00018a017 Adenosine receptor A2a 2
1495019 10.1021/jm00093a022 Rattus norvegicus 2
10479279 10.1021/jm960682u Mus musculus 2
19569717 10.1021/jm900413e Adenosine receptor A2b 2
18243699 10.1016/j.bmcl.2008.01.033 Cavia porcellus 2
7658444 10.1021/jm00018a017 Adenosine receptor A1 2
10212124 10.1021/jm9804984 Adenosine receptor A2a 2
10212124 10.1021/jm9804984 Adenosine receptor A1 2
7739005 10.1021/jm00009a007 Adenosine receptor A1 2
11784146 10.1021/jm010952v Adenosine receptor A2a 2
20031406 10.1016/j.bmcl.2009.11.131 Adenosine receptor A2a 2

Data from ChEMBL 36 via Core Engine