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Compound Detail

CHEMBL27376

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

Basic Information

ChEMBL ID CHEMBL27376
Phase Preclinical
Structure Type MOL
InChI Key AGCJNWSEWOWGRS-DDDALXFXSA-N
9
Targets
22
Activities
3
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

554.8
MW (Da)
1.73
ALogP
8
HBA
4
HBD
125.2
PSA (Ų)
0.28
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H20ClIN6O3
MW 554.78
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.39

Activity Summary

Ki 20 meas. best 9.1
EC50 1 meas. best 5.28
Kd 1 meas. best 9.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A3
CHEMBL3360
 Kd 9.77 9.77 0.2 1
Adenosine receptor A3
CHEMBL1075269
 Ki 9.1 9.1 0.8 1
Adenosine receptor A3
CHEMBL3360
 Ki 8.96 8.96 1.1 2
Adenosine receptor A3
CHEMBL256
 Ki 8.82 8.226 1.5 5
Adenosine receptor A1
CHEMBL3688
 Ki 8.13 8.13 7.3 1
Adenosine receptor A1
CHEMBL318
 Ki 7.08 7.08 83.9 2
Adenosine receptor A1
CHEMBL226
 Ki 6.87 6.87 136.0 3
Adenosine receptor A2a
CHEMBL251
 Ki 6.11 6.11 784.0 3
Adenosine receptor A2a
CHEMBL302
 Ki 5.78 5.78 1660.0 2
Adenosine receptor A3
CHEMBL256
 EC50 5.28 5.28 5250.0 1
Adenosine receptor A2a
CHEMBL2115
 Ki 5.27 5.27 5350.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A3 Kd = 0.17 nM 9.77 Binding affinity to rat adenosine A3 receptor measured by radioligand binding as... 35450351
Adenosine receptor A3 Ki = 0.8 nM 9.1 Displacement of [125I]N6-(-amino-3-iodobenzyl)adenosine-5'-N-methyl-uronamide fr... 18424135
Adenosine receptor A3 Ki = 1.1 nM 8.96 Inhibition of [125I]AB-MECA binding to rat Adenosine A3 receptor expressed in CH... 15771421
Adenosine receptor A3 Ki = 1.1 nM 8.96 Displacement of radioligand from rat A3 adenosine receptor 18424135
Adenosine receptor A3 Ki = 1.51 nM 8.82 Ability to displace specific radioligand [125I]AB-MECA binding at human Adenosin... 11392549
Adenosine receptor A3 Ki = 1.5 nM 8.82 Inhibition of [125I]-AB-MECA binding to human Adenosine A3 receptor expressed in... 15771421
Adenosine receptor A3 Ki = 1.5 nM 8.82 Displacement of radioligand from human adenosine A3 receptor expressed in CHO ce... 18424135
Adenosine receptor A3 Ki = 1.5 nM 8.82 Displacement of [3H]CGS21680 form human adenosine A3 receptor expressed in CHO c... 18752961
Adenosine receptor A1 Ki = 7.32 nM 8.13 Displacement of [125I]N6-(4-amino-3-iodobenzyl)adenosine-5'-N-methyl-uronamide f... 18424135
Adenosine receptor A1 Ki = 83.9 nM 7.08 Displacement of radioligand from rat adenosine A1 receptor 18424135
Adenosine receptor A1 Ki = 83.9 nM 7.08 Ability to displace specific radioligand [3H]R-PIA binding at Adenosine A1 recep... 11392549
Adenosine receptor A1 Ki = 136.0 nM 6.87 Inhibition of [3H]R-PIA binding to human Adenosine A1 receptor expressed in CHO ... 15771421
Adenosine receptor A1 Ki = 136.0 nM 6.87 Displacement of radioligand from human adenosine A1 receptor expressed in CHO ce... 18424135
Adenosine receptor A1 Ki = 136.0 nM 6.87 Displacement of [3H]CCPA form human adenosine A1 receptor expressed in CHO cells 18752961
Adenosine receptor A2a Ki = 784.0 nM 6.11 Inhibition of [3H]-CGS- 21680 binding to human Adenosine A2A receptor expressed ... 15771421
Adenosine receptor A2a Ki = 784.0 nM 6.11 Displacement of radioligand from human adenosine A2A receptor expressed in HEK29... 18424135
Adenosine receptor A2a Ki = 784.0 nM 6.11 Displacement of [3H]R-PIA form human adenosine A2A receptor expressed in HEK cel... 18752961
Adenosine receptor A3 Ki = 1400.0 nM 5.85 Binding affinity to human adenosine A3 receptor measured by radioligand binding ... 35450351
Adenosine receptor A2a Ki = 1660.0 nM 5.78 Ability to displace specific radioligand [3H]-CGS- 21680 binding at A2A receptor... 11392549
Adenosine receptor A2a Ki = 1660.0 nM 5.78 Displacement of radioligand from rat adenosine A2A receptor 18424135

Literature References

PubMed DOI Target Context # Activities
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A3 3
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A2a 3
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A1 3
15771421 10.1021/jm049580r Adenosine receptor A3 3
35450351 10.1021/acsmedchemlett.1c00685 Adenosine receptor A3 2
18752961 10.1016/j.bmc.2008.08.007 Adenosine receptor A3 2
18424135 10.1016/j.bmcl.2008.04.001 Unchecked 2
11392549 10.1016/s0960-894x(01)00213-x Adenosine receptor A3 2
15771421 10.1021/jm049580r Adenosine receptor A2b 1
15771421 10.1021/jm049580r Adenosine receptor A2a 1
15771421 10.1021/jm049580r Adenosine receptor A1 1
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptors; A1 & A3 1
18424135 10.1016/j.bmcl.2008.04.001 Adenosine receptor A2b 1
18752961 10.1016/j.bmc.2008.08.007 Adenosine receptor A1 1
18752961 10.1016/j.bmc.2008.08.007 Adenosine receptor A2a 1
11392549 10.1016/s0960-894x(01)00213-x Adenosine receptor A2a 1
11392549 10.1016/s0960-894x(01)00213-x Adenosine receptor A1 1

Data from ChEMBL 36 via Core Engine