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Compound Detail

CHEMBL1627305

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O=C(NCCC(O)CN1CCN(c2cccc(Cl)c2Cl)CC1)c1cc2ccccc2[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1627305
Phase Preclinical
Structure Type MOL
InChI Key NABHHUMHJIHHIX-UHFFFAOYSA-N
8
Targets
31
Activities
3
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

461.4
MW (Da)
3.78
ALogP
4
HBA
3
HBD
71.6
PSA (Ų)
0.50
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H26Cl2N4O2
MW 461.39
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.19

Activity Summary

Ki 24 meas. best 9.05
IC50 5 meas. best 7.52
EC50 2 meas. best 6.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
D(3) dopamine receptor
CHEMBL234
 Ki 9.05 8.6682 0.9 11
D(3) dopamine receptor
CHEMBL234
 IC50 7.52 7.1133 29.9 3
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 7.32 7.32 48.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 7.07 7.07 86.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.0 6.99 100.0 2
D(2) dopamine receptor
CHEMBL217
 EC50 6.77 6.77 170.0 1
Unchecked
CHEMBL612545
 EC50 6.77 6.77 171.2 1
Unchecked
CHEMBL612545
 Ki 6.3 6.3 502.0 1
D(2) dopamine receptor
CHEMBL217
 Ki 6.13 6.1275 746.0 4
D(4) dopamine receptor
CHEMBL219
 Ki 5.58 5.49 2600.0 3
D(2) dopamine receptor
CHEMBL217
 IC50 5.36 5.36 4400.0 1
Unchecked
CHEMBL612545
 IC50 5.36 5.36 4370.0 1
D(1A) dopamine receptor
CHEMBL2056
 Ki 5.33 5.33 4630.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 7971.0 ng.hr.mL-1 Mus musculus
AUC 8895000.0 ng.hr.mL-1 Mus musculus
AUC 1299.0 ng.hr.mL-1 Mus musculus
Cmax 15971.3 nM Mus musculus
Cmax 1131.36 nM Mus musculus
F 16.22 % Mus musculus
T1/2 1.241 hr Mus musculus
T1/2 0.3133 hr Mus musculus
Tmax 0.08 hr Mus musculus
Tmax 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
D(3) dopamine receptor Ki = 0.9 nM 9.05 Binding Assay: Methods for performing in vitro dopamine receptor binding studies... -
D(3) dopamine receptor Ki = 0.9 nM 9.05 Binding Assay: Methods for performing in vitro dopamine receptor binding studies... -
D(3) dopamine receptor Ki = 1.1 nM 8.96 Binding Assay: Methods for performing in vitro dopamine receptor binding studies... -
D(3) dopamine receptor Ki = 1.1 nM 8.96 Binding Assay: Methods for performing in vitro dopamine receptor binding studies... -
D(3) dopamine receptor Ki = 1.39 nM 8.86 Displacement of [125]IABN from human D3 receptor expressed in HEK293 cells 19331412
D(3) dopamine receptor Ki = 1.88 nM 8.73 Displacement of [3H]-N-methylspiperone from human dopamine D3 receptor (unknown ... 26203768
D(3) dopamine receptor Ki = 1.88 nM 8.73 Displacement of [3H]-N-methylspiperone from human dopamine D3 receptor expressed... 25650314
D(3) dopamine receptor Ki = 1.88 nM 8.73 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor expressed ... 24848155
D(3) dopamine receptor Ki = 1.9 nM 8.72 Displacement of [3H]N-methylspiperone from human dopamine D3 receptor expressed ... 24944737
D(3) dopamine receptor Ki = 16.5 nM 7.78 Binding Assay: Methods for performing in vitro dopamine receptor binding studies... -
D(3) dopamine receptor Ki = 16.5 nM 7.78 Binding Assay: Methods for performing in vitro dopamine receptor binding studies... -
D(3) dopamine receptor IC50 = 30.0 nM 7.52 Antagonist activity at human dopamine D3 receptor expressed in CHO cells assesse... 26203768
D(3) dopamine receptor IC50 = 29.9 nM 7.52 Antagonist activity at human D3 receptor expressed in HEK293 cells assessed as i... 19331412
5-hydroxytryptamine receptor 2A Ki = 48.0 nM 7.32 Displacement of [125I]DOI from 5HT2A receptor (unknown origin) 26203768
5-hydroxytryptamine receptor 2C Ki = 86.0 nM 7.07 Displacement of [125I]DOI from 5HT2C receptor (unknown origin) 26203768
5-hydroxytryptamine receptor 1A Ki = 100.0 nM 7.0 Displacement of [3H]-8-OH-DPAT from 5HT1A receptor (unknown origin) 26203768
5-hydroxytryptamine receptor 1A Ki = 104.0 nM 6.98 Displacement of [3H]8-OH-DPAT from 5HT1A receptor 19331412
D(2) dopamine receptor EC50 = 170.0 nM 6.77 Agonist activity at human dopamine D2 receptor expressed in CHO cells assessed a... 26203768
Unchecked EC50 = 171.2 nM 6.77 Agonist activity at human D2 like receptor expressed in HEK293 cells assessed as... 19331412
D(3) dopamine receptor IC50 = 495.0 nM 6.3 Antagonist activity at human dopamine D3 receptor expressed in CHO-K1 cells asse... 21495689

Literature References

PubMed DOI Target Context # Activities
25826710 10.1021/jm501512b Mus musculus 10
25826710 10.1021/jm501512b ADMET 8
19331412 10.1021/jm900095y Unchecked 6
25826710 10.1021/jm501512b Rhesus monkey 5
25826710 10.1021/jm501512b Cynomolgus monkey 5
26203768 10.1021/acs.jmedchem.5b00776 D(3) dopamine receptor 4
25826710 10.1021/jm501512b Brain 4
26203768 10.1021/acs.jmedchem.5b00776 D(2) dopamine receptor 4
26203768 10.1021/acs.jmedchem.5b00776 5-hydroxytryptamine receptor 1A 3
25826710 10.1021/jm501512b Plasma 3
19331412 10.1021/jm900095y D(3) dopamine receptor 2
25826710 10.1021/jm501512b Nucleic Acid 2
24944737 10.1021/ml500006v D(2) dopamine receptor 1
24944737 10.1021/ml500006v Unchecked 1
24944737 10.1021/ml500006v D(3) dopamine receptor 1
24848155 10.1021/jm401798r Unchecked 1
24848155 10.1021/jm401798r D(3) dopamine receptor 1
21495689 10.1021/jm200288r 5-hydroxytryptamine receptor 2A 1
21495689 10.1021/jm200288r D(3) dopamine receptor 1
19331412 10.1021/jm900095y 5-hydroxytryptamine receptor 1A 1

Data from ChEMBL 36 via Core Engine