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Compound Detail

CHEMBL27559

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CCCN1CCc2cccc3c2[C@H]1Cc1cccc(O)c1-3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL27559
Phase Preclinical
Structure Type MOL
InChI Key WZJSIHGOLMMBAL-MRXNPFEDSA-N
11
Targets
33
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

279.4
MW (Da)
3.92
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.90
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H21NO
MW 279.38
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.83

Activity Summary

Ki 30 meas. best 9.05
IC50 3 meas. best 7.44

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(2) dopamine receptor
CHEMBL339
 Ki 9.05 7.7425 0.9 8
D(3) dopamine receptor
CHEMBL234
 Ki 8.92 7.345 1.2 2
Dopamine receptor
CHEMBL2093868
 Ki 8.4 8.34 4.0 2
D(2) dopamine receptor
CHEMBL217
 Ki 7.9 7.46 12.7 3
Unchecked
CHEMBL612545
 Ki 7.62 7.62 24.0 1
Dopamine receptor
CHEMBL2093868
 IC50 7.44 6.8 36.0 2
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 7.4 7.4 39.5 2
D(1A) dopamine receptor
CHEMBL2056
 Ki 7.35 6.2933 45.0 3
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.35 7.35 45.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 6.94 6.94 114.0 1
D(1A) dopamine receptor
CHEMBL265
 Ki 6.36 6.1886 434.0 7
Tyrosine 3-monooxygenase
CHEMBL1969
 IC50 4.38 4.38 42000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(2) dopamine receptor Ki = 0.9 nM 9.05 Compound was evaluated for its ability to inhibit Dopamine receptor D2 in rat st... 1671415
D(3) dopamine receptor Ki = 1.2 nM 8.92 Displacement of [3H]domperidone from human cloned dopamine D3 receptor high bind... 21666830
D(2) dopamine receptor Ki = 2.7 nM 8.57 Binding affinity against Dopamine receptor D2 from rat brain corpus striatal pre... 3385732
Dopamine receptor Ki = 4.0 nM 8.4 Binding affinity against dopamine agonist sites from rat brain corpus striatal p... 3385732
D(2) dopamine receptor Ki = 4.9 nM 8.31 Displacement of [3H]domperidone from dopamine D2 receptor high binding site in S... 21666830
Dopamine receptor Ki = 5.3 nM 8.28 Compound was evaluated for its ability to inhibit Striatal Dopamine receptor in ... 1671415
D(2) dopamine receptor Ki = 12.7 nM 7.9 Displacement of [3H]raclopride from human Dopamine receptor D2A 8784448
Unchecked Ki = 24.0 nM 7.62 Selectivity ratio of Ki for dopamine D1 receptor to Ki for dopamine D2 receptor ... 19058967
D(2) dopamine receptor Ki = 28.5 nM 7.54 Binding affinity to D2 receptor (unknown origin) assessed as inhibition constant 39038276
D(2) dopamine receptor Ki = 28.5 nM 7.54 Displacement of [3H]neomonapride from dopamine D2 receptor in rat corpus striatu... 18585036
D(2) dopamine receptor Ki = 29.0 nM 7.54 Displacement of [3H]raclopride from rat dopamine D2 receptor 17228858
D(2) dopamine receptor Ki = 28.5 nM 7.54 Displacement of [3H]neomonapride from dopamine D2 receptor in rat striatum 18251489
D(2) dopamine receptor Ki = 28.5 nM 7.54 Displacement of [3H]nemonapride from dopamine D2 receptor in rat forebrain 19058967
Dopamine receptor IC50 = 36.0 nM 7.44 Inhibition of [3H]apomorphine binding to calf caudate membrane preparation (p4) 7310821
5-hydroxytryptamine receptor 1A Ki = 39.5 nM 7.4 In vitro displacement of [3H]8-OH-DPAT binding to rat hippocampal 5-hydroxytrypt... 8784448
5-hydroxytryptamine receptor 1A Ki = 40.0 nM 7.4 Displacement of [3H]8-OH-DPAT from rat 5HT1A receptor 17228858
D(1A) dopamine receptor Ki = 45.0 nM 7.35 Displacement of [3H]8OH-DPAT from human dopamine D1 receptor expressed in HEK293... 18783955
5-hydroxytryptamine receptor 1A Ki = 45.0 nM 7.35 Displacement of [3H]8-OH-DPAT from 5HT1A receptor expressed in CHO cells by liqu... 20041669
5-hydroxytryptamine receptor 2A Ki = 114.0 nM 6.94 Displacement of [3H]Spiperone from human 5HT2A receptor expressed in HEK293 cell... 18783955
D(2) dopamine receptor Ki = 114.0 nM 6.94 Displacement of [3H]spiperone from dopamine D2 receptor expressed in HEK293 cell... 20041669

Literature References

PubMed DOI Target Context # Activities
8784448 10.1021/jm960189i Rattus norvegicus 6
3385732 10.1021/jm00402a024 Rattus norvegicus 6
21666830 10.1021/ml1001689 D(2) dopamine receptor 2
21666830 10.1021/ml1001689 D(3) dopamine receptor 2
7310821 10.1021/jm00144a014 Dopamine receptor 2
21666830 10.1021/ml1001689 D(1A) dopamine receptor 2
3385732 10.1021/jm00402a024 Dopamine D1 and D2 receptor 1
17228858 10.1021/jm060959i D(2) dopamine receptor 1
17228858 10.1021/jm060959i D(1A) dopamine receptor 1
17228858 10.1021/jm060959i Unchecked 1
8784448 10.1021/jm960189i D(2) dopamine receptor 1
8784448 10.1021/jm960189i D(1A) dopamine receptor 1
8784448 10.1021/jm960189i 5-hydroxytryptamine receptor 1A 1
1671415 10.1021/jm00105a005 Dopamine receptor 1
39038276 10.1021/acs.jmedchem.4c00537 D(2) dopamine receptor 1
3385732 10.1021/jm00402a024 D(2) dopamine receptor 1
3385732 10.1021/jm00402a024 D(1A) dopamine receptor 1
7310821 10.1021/jm00144a014 Adenylate cyclase 1
1671415 10.1021/jm00105a005 Dopamine D1 and D2 receptor 1
1671415 10.1021/jm00105a005 D(2) dopamine receptor 1

Data from ChEMBL 36 via Core Engine