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Compound Detail

CHEMBL8565

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CCCn1c(=O)[nH]c2nc(-c3ccc(S(=O)(=O)O)cc3)[nH]c2c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL8565
Phase Preclinical
Structure Type MOL
InChI Key UYDRRQPGDSIMNU-UHFFFAOYSA-N
8
Targets
21
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

350.4
MW (Da)
0.74
ALogP
6
HBA
3
HBD
137.9
PSA (Ų)
0.59
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H14N4O5S
MW 350.36
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.95

Activity Summary

Ki 21 meas. best 7.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A2b
CHEMBL255
 Ki 7.27 7.1467 53.4 9
Adenosine receptor A1
CHEMBL3688
 Ki 6.23 6.23 591.0 1
Adenosine receptor A1
CHEMBL318
 Ki 5.91 5.7225 1238.0 4
Adenosine receptor A2b
CHEMBL2237
 Ki 5.71 5.71 1940.0 1
Adenosine receptor A2b
CHEMBL2592
 Ki 5.5 5.5 3140.0 1
Adenosine receptor A2a
CHEMBL251
 Ki 5.42 5.42 3790.0 1
Adenosine receptor A2a
CHEMBL302
 Ki 4.93 4.7233 11800.0 3
Adenosine A2 receptor
CHEMBL2094117
 Ki 4.62 4.62 24000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A2b Ki = 53.4 nM 7.27 Displacement of [3H]ZM241385 from human recombinant Adenosine A2B receptor 26824742
Adenosine receptor A2b Ki = 53.4 nM 7.27 Displacement of [3H]ZM241385 from human recombinant adenosine A2B receptor 28368607
Adenosine receptor A2b Ki = 53.4 nM 7.27 Displacement of [3H]ZM241385 from recombinant human A2B adenosine receptor expre... 30835463
Adenosine receptor A2b Ki = 53.4 nM 7.27 Antagonist activity at human A2B receptor 33372800
Adenosine receptor A2b Ki = 53.4 nM 7.27 Displacement of [125I]IABOPX to human A2B receptor assessed as inhibition consta... 34019396
Adenosine receptor A2b Ki = 53.4 nM 7.27 Antagonist activity at adenosine 2B receptor (unknown origin) 38483150
Adenosine receptor A2b Ki = 53.4 nM 7.27 Displacement of [3H]ZM-241385 from human recombinant adenosine A2B receptor expr... 16821798
Adenosine receptor A2b Ki = 190.55 nM 6.72 Displacement of [3H]PSB-603 from human adenosine A2B receptor expressed in CHO c... 35923720
Adenosine receptor A2b Ki = 194.98 nM 6.71 Displacement of [3H]PSB-603 from human adenosine A2B receptor expressed in CHO c... 35923720
Adenosine receptor A1 Ki = 591.0 nM 6.23 Displacement of [3H]DPCPX from recombinant mouse A1 adenosine receptor expressed... 30835463
Adenosine receptor A1 Ki = 1238.0 nM 5.91 Displacement of [3H]-CCPA from adenosine A1 receptor of rat brain cortical membr... 14761205
Adenosine receptor A2b Ki = 1940.0 nM 5.71 Displacement of [3H]PSB-603 from recombinant mouse A2B adenosine receptor expres... 30835463
Adenosine receptor A1 Ki = 2200.0 nM 5.66 Binding affinity at Adenosine A1 receptor in rat brain cortical membrane using [... 8230124
Adenosine receptor A1 Ki = 2200.0 nM 5.66 Displacement of [3H]R-PIA from adenosine A1 receptor in rat brain cortical membr... 16821798
Adenosine receptor A1 Ki = 2200.0 nM 5.66 Displacement of [3H]CCPA from A1 adenosine receptor in rat cortex membranes meas... 30835463
Adenosine receptor A2b Ki = 3140.0 nM 5.5 Displacement of [3H]PSB-603 from recombinant rat A2B adenosine receptor expresse... 30835463
Adenosine receptor A2a Ki = 3790.0 nM 5.42 Displacement of [3H]MSX-2 from recombinant human A2A adenosine receptor expresse... 30835463
Adenosine receptor A2a Ki = 11800.0 nM 4.93 Displacement of [3H]MSX-2 from adenosine A2A receptor of rat brain striatal memb... 14761205
Adenosine A2 receptor Ki = 24000.0 nM 4.62 Binding affinity against Adenosine A2 receptor in rat striatal membranes using [... 8230124
Adenosine receptor A2a Ki = 24000.0 nM 4.62 Displacement of [3H]R-PIA from adenosine A2A receptor in rat brain striatal memb... 16821798

Literature References

PubMed DOI Target Context # Activities
35923720 10.1039/d2md00132b Adenosine receptor A2b 4
30835463 10.1021/acs.jmedchem.9b00071 Adenosine receptor A1 3
30835463 10.1021/acs.jmedchem.9b00071 Adenosine receptor A2a 3
30835463 10.1021/acs.jmedchem.9b00071 Adenosine receptor A2b 3
30835463 10.1021/acs.jmedchem.9b00071 Adenosine receptor A3 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
16821798 10.1021/jm060277v Adenosine receptor A2a 2
16821798 10.1021/jm060277v Adenosine receptor A1 2
26824742 10.1021/acs.jmedchem.5b01586 Adenosine receptor A2b 1
38483150 10.1021/acs.jmedchem.4c00250 Adenosine receptor A2b 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
28368607 10.1021/acs.jmedchem.7b00138 Adenosine receptor A2b 1
14761205 10.1021/jm0310030 Adenosine receptor A1 1
16821798 10.1021/jm060277v Adenosine receptor A2b 1
16821798 10.1021/jm060277v Adenosine receptor A3 1
8230124 10.1021/jm00074a015 Adenosine A2 receptor 1
8230124 10.1021/jm00074a015 Adenosine receptor A1 1
14761205 10.1021/jm0310030 Adenosine receptor A3 1
14761205 10.1021/jm0310030 Adenosine receptor A2b 1

Data from ChEMBL 36 via Core Engine