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Compound Detail

CHEMBL4572614

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Cc1ncc2nccn2c1-c1ccc(Oc2nccc3occc23)cc1C(F)(F)F

Basic Information

ChEMBL ID CHEMBL4572614
Phase Preclinical
Structure Type MOL
InChI Key GEPUWJGKAOGNRH-UHFFFAOYSA-N
26
Targets
30
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

410.4
MW (Da)
5.66
ALogP
6
HBA
0
HBD
65.5
PSA (Ų)
0.38
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H13F3N4O2
MW 410.36
Aromatic Rings 5
Heavy Atoms 30
NP-Likeness -0.90

Activity Summary

Ki 26 meas. best 7.09
EC50 4 meas. best 8.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(1A) dopamine receptor
CHEMBL2056
EC50 8.77 7.7025 1.7 4
D(1B) dopamine receptor
CHEMBL1850
Ki 7.09 7.09 82.0 1
D(1A) dopamine receptor
CHEMBL2056
Ki 6.85 6.85 140.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.17 5.17 6800.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.17 5.17 6700.0 1
D(4) dopamine receptor
CHEMBL219
Ki 5.16 5.16 6900.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 5.16 5.16 6900.0 1
Kappa-type opioid receptor
CHEMBL237
Ki 5.14 5.14 7200.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 5.14 5.14 7300.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 5.1 5.1 8000.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 5.1 5.1 7900.0 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 5.09 5.09 8100.0 1
D(3) dopamine receptor
CHEMBL234
Ki 5.09 5.09 8100.0 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
Ki 5.09 5.09 8100.0 1
Histamine H2 receptor
CHEMBL1941
Ki 5.09 5.09 8200.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 5.07 5.07 8500.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 5.06 5.06 8700.0 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 5.06 5.06 8700.0 1
Alpha-1B adrenergic receptor
CHEMBL232
Ki 5.06 5.06 8800.0 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
Ki 5.06 5.06 8800.0 1
5-hydroxytryptamine receptor 1E
CHEMBL2182
Ki 5.05 5.05 8900.0 1
5-hydroxytryptamine receptor 3A
CHEMBL1899
Ki 5.04 5.04 9100.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 5.04 5.04 9200.0 1
Mu-type opioid receptor
CHEMBL233
Ki 5.03 5.03 9400.0 1
5-hydroxytryptamine receptor 5A
CHEMBL3426
Ki 5.02 5.02 9500.0 1
D(2) dopamine receptor
CHEMBL217
Ki 5.02 5.02 9600.0 1
Beta-1 adrenergic receptor
CHEMBL213
Ki 5.02 5.02 9600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(1A) dopamine receptor EC50 = 1.7 nM 8.77 Agonist activity at recombinant human D1 receptor expressed in HEK29T cells asse... 30875219
D(1A) dopamine receptor EC50 = 1.738 nM 8.76 Agonist activity at recombinant human D1 receptor expressed in HEK29T cells asse... 30875219
D(1B) dopamine receptor Ki = 82.0 nM 7.09 Displacement of [3H]-SCH23390 from recombinant human D5 receptor transiently exp... 30875219
D(1A) dopamine receptor Ki = 140.0 nM 6.85 Displacement of [3H]-SCH23390 from recombinant human D1 receptor transiently exp... 30875219
D(1A) dopamine receptor EC50 = 230.0 nM 6.64 Agonist activity at recombinant C-terminal RLuc8-fused human D1 receptor express... 30875219
D(1A) dopamine receptor EC50 = 229.09 nM 6.64 Agonist activity at recombinant C-terminal RLuc8-fused human D1 receptor express... 30875219
5-hydroxytryptamine receptor 2B Ki = 6700.0 nM 5.17 Displacement of [3H]-LSD from recombinant human 5HT2B receptor stably expressed ... 30875219
Alpha-2A adrenergic receptor Ki = 6800.0 nM 5.17 Displacement of [3H]-rauwolscine from recombinant human alpha2A adrenergic recep... 30875219
D(4) dopamine receptor Ki = 6900.0 nM 5.16 Displacement of [3H]-N-methylspiperone from recombinant human D4 receptor stably... 30875219
5-hydroxytryptamine receptor 1A Ki = 6900.0 nM 5.16 Displacement of [3H]-Way100635 from recombinant human 5HT1A receptor stably expr... 30875219
Kappa-type opioid receptor Ki = 7200.0 nM 5.14 Displacement of [3H]-U69593 from KOR (unknown origin) measured after 90 mins by ... 30875219
Muscarinic acetylcholine receptor M2 Ki = 7300.0 nM 5.14 Displacement of [3H]-QNB/[3H]-NMS from human muscarinic M2 receptor expressed in... 30875219
5-hydroxytryptamine receptor 6 Ki = 7900.0 nM 5.1 Displacement of [3H]-LSD from recombinant human 5HT6 receptor stably expressed i... 30875219
Sigma non-opioid intracellular receptor 1 Ki = 8000.0 nM 5.1 Displacement of [3H]-pentazocine from sigma1 receptor (unknown origin) after 90 ... 30875219
5-hydroxytryptamine receptor 1D Ki = 8100.0 nM 5.09 Displacement of [3H]5-CT from recombinant human 5HT1D receptor transiently expre... 30875219
Histamine H2 receptor Ki = 8200.0 nM 5.09 Displacement of [125I]-Iodo-aminopotentidine from human histamine H2 receptor ex... 30875219
5-hydroxytryptamine receptor 7 Ki = 8100.0 nM 5.09 Displacement of [3H]-LSD from recombinant human 5HT7A receptor stably expressed ... 30875219
D(3) dopamine receptor Ki = 8100.0 nM 5.09 Displacement of [3H]-N-methylspiperone from D3 receptor (unknown origin) measure... 30875219
Muscarinic acetylcholine receptor M1 Ki = 8500.0 nM 5.07 Displacement of [3H]-QNB/[3H]-NMS from human muscarinic M1 receptor expressed in... 30875219
5-hydroxytryptamine receptor 1B Ki = 8800.0 nM 5.06 Displacement of [3H]5-CT from recombinant human 5HT1B receptor stably expressed ... 30875219

Literature References

PubMed DOI Target Context # Activities
30875219 10.1021/acs.jmedchem.9b00351 D(1A) dopamine receptor 8
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 2B 1
30875219 10.1021/acs.jmedchem.9b00351 Sodium-dependent serotonin transporter 1
30875219 10.1021/acs.jmedchem.9b00351 Beta-1 adrenergic receptor 1
30875219 10.1021/acs.jmedchem.9b00351 Alpha-2A adrenergic receptor 1
30875219 10.1021/acs.jmedchem.9b00351 Alpha-1B adrenergic receptor 1
30875219 10.1021/acs.jmedchem.9b00351 Alpha-1A adrenergic receptor 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 7 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 6 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 5A 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 4 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 3A 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 2A 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 1E 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 1D 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 1B 1
30875219 10.1021/acs.jmedchem.9b00351 5-hydroxytryptamine receptor 1A 1
30875219 10.1021/acs.jmedchem.9b00351 D(1B) dopamine receptor 1
30875219 10.1021/acs.jmedchem.9b00351 D(4) dopamine receptor 1
30875219 10.1021/acs.jmedchem.9b00351 D(3) dopamine receptor 1

Data from ChEMBL 36 via Core Engine