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Compound Detail

CHEMBL175543

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CNC(=O)[C@@]12C[C@@H]1[C@@H](n1cnc3c(NCc4cccc(Cl)c4)nc(Cl)nc31)[C@H](O)[C@@H]2O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL175543
Phase Preclinical
Structure Type MOL
InChI Key GAYWHRPOIWFKIF-DDDALXFXSA-N
8
Targets
21
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

463.3
MW (Da)
1.77
ALogP
8
HBA
4
HBD
125.2
PSA (Ų)
0.43
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 C20H20Cl2N6O3
MW 463.33
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.36

Activity Summary

Ki 20 meas. best 9.54
IC50 1 meas. best 5.49

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A3
CHEMBL256
 Ki 9.54 9.54 0.3 5
Adenosine receptor A3
CHEMBL3360
 Ki 9.0 9.0 1.0 2
Adenosine receptor A3
CHEMBL1075269
 Ki 8.83 8.83 1.5 1
Adenosine receptor A1
CHEMBL3688
 Ki 7.82 7.82 15.3 1
Adenosine receptor A1
CHEMBL226
 Ki 6.58 6.58 260.0 5
Adenosine receptor A2a
CHEMBL251
 Ki 5.64 5.64 2300.0 5
5-hydroxytryptamine receptor 2B
CHEMBL1833
 IC50 5.49 5.49 3260.0 1
Adenosine receptor A2a
CHEMBL2115
 Ki 4.98 4.98 10400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A3 Ki = 0.29 nM 9.54 Inhibition of [125I]-AB-MECA binding to human Adenosine A3 receptor expressed in... 15771421
Adenosine receptor A3 Ki = 0.29 nM 9.54 Displacement of radioligand from human adenosine A3 receptor expressed in CHO ce... 18424135
Adenosine receptor A3 Ki = 0.29 nM 9.54 Displacement of [3H]CGS21680 form human adenosine A3 receptor expressed in CHO c... 18752961
Adenosine receptor A3 Ki = 0.29 nM 9.54 Displacement of [3H]I-AB-MECA from human recombinant adenosine A3 receptor expre... 22559880
Adenosine receptor A3 Ki = 0.29 nM 9.54 Displacement of [125I]I-AB-MECA from human recombinant adenosine A3 receptor exp... 22468757
Adenosine receptor A3 Ki = 1.0 nM 9.0 Inhibition of [125I]AB-MECA binding to rat Adenosine A3 receptor expressed in CH... 15771421
Adenosine receptor A3 Ki = 1.0 nM 9.0 Displacement of [125I]I-AB-MECA from human rat adenosine A3 receptor expressed i... 22468757
Adenosine receptor A3 Ki = 1.49 nM 8.83 Displacement of [125I]N6-(-amino-3-iodobenzyl)adenosine-5'-N-methyl-uronamide fr... 18424135
Adenosine receptor A1 Ki = 15.3 nM 7.82 Displacement of [125I]N6-(4-amino-3-iodobenzyl)adenosine-5'-N-methyl-uronamide f... 18424135
Adenosine receptor A1 Ki = 260.0 nM 6.58 Inhibition of [3H]R-PIA binding to human Adenosine A1 receptor expressed in CHO ... 15771421
Adenosine receptor A1 Ki = 260.0 nM 6.58 Displacement of [3H]CCPA from human recombinant adenosine A1 receptor expressed ... 22468757
Adenosine receptor A1 Ki = 260.0 nM 6.58 Displacement of [3H]R-PIA from human recombinant adenosine A1 receptor expressed... 22559880
Adenosine receptor A1 Ki = 260.0 nM 6.58 Displacement of [3H]CCPA form human adenosine A1 receptor expressed in CHO cells 18752961
Adenosine receptor A1 Ki = 260.0 nM 6.58 Displacement of radioligand from human adenosine A1 receptor expressed in CHO ce... 18424135
Adenosine receptor A2a Ki = 2300.0 nM 5.64 Inhibition of [3H]-CGS- 21680 binding to human Adenosine A2A receptor expressed ... 15771421
Adenosine receptor A2a Ki = 2300.0 nM 5.64 Displacement of radioligand from human adenosine A2A receptor expressed in HEK29... 18424135
Adenosine receptor A2a Ki = 2300.0 nM 5.64 Displacement of [3H]R-PIA form human adenosine A2A receptor expressed in HEK cel... 18752961
Adenosine receptor A2a Ki = 2300.0 nM 5.64 Displacement of [3H]CGS21680 from human recombinant adenosine A2A receptor expre... 22559880
Adenosine receptor A2a Ki = 2300.0 nM 5.64 Displacement of [3H]CGS21680 from human recombinant adenosine A2A receptor expre... 22468757
5-hydroxytryptamine receptor 2B IC50 = 3260.0 nM 5.49 Antagonist activity at human 5-HT2BR expressed in Flp-In HEK cells assessed as i... 27933810

Literature References

PubMed DOI Target Context # Activities
15771421 10.1021/jm049580r Adenosine receptor A3 3
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A1 3
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A2a 3
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A3 3
22468757 10.1021/jm300087j Adenosine receptor A3 2
22559880 10.1021/jm300396n Adenosine receptor A3 2
18752961 10.1016/j.bmc.2008.08.007 Adenosine receptor A3 2
18752961 10.1016/j.bmc.2008.08.007 Adenosine receptor A1 1
27933810 10.1021/acs.jmedchem.6b01183 5-hydroxytryptamine receptor 2B 1
22468757 10.1021/jm300087j Adenosine receptor A2a 1
22468757 10.1021/jm300087j Unchecked 1
22559880 10.1021/jm300396n Adenosine receptor A2a 1
22559880 10.1021/jm300396n Adenosine receptor A1 1
22559880 10.1021/jm300396n Unchecked 1
18752961 10.1016/j.bmc.2008.08.007 Adenosine receptor A2a 1
15771421 10.1021/jm049580r Adenosine receptor A1 1
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A2b 1
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptors; A1 & A3 1
18424135 10.1016/j.bmcl.2008.04.001 Unchecked 1
15771421 10.1021/jm049580r Adenosine receptor A2b 1

Data from ChEMBL 36 via Core Engine