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Compound Detail

CHEMBL3918282

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[O-][S+](CCN1CCN(CC(O)Cc2ccccc2)CC1)C(c1ccc(F)cc1)c1ccc(F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3918282
Phase Preclinical
Structure Type MOL
InChI Key MACFTPBZAOCTFN-UHFFFAOYSA-N
9
Targets
32
Activities
1
Assay Types
1
PK Parameters
19
Publications
0
Known Names

Molecular Properties

498.6
MW (Da)
4.02
ALogP
4
HBA
1
HBD
49.8
PSA (Ų)
0.43
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H32F2N2O2S
MW 498.64
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -0.53

Activity Summary

Ki 32 meas. best 9.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
 Ki 9.09 8.2925 0.8 4
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 8.6 8.598 2.5 5
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Ki 7.38 6.925 41.6 2
D(2) dopamine receptor
CHEMBL217
 Ki 7.11 7.11 78.6 2
Unchecked
CHEMBL612545
 Ki 7.01 6.02 97.0 8
D(3) dopamine receptor
CHEMBL234
 Ki 6.19 6.19 652.0 2
D(4) dopamine receptor
CHEMBL219
 Ki 5.76 5.76 1750.0 2
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 5.34 5.252 4610.0 5
Transporter
CHEMBL6184
 Ki 4.82 4.82 15000.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.2167 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter Ki = 0.806 nM 9.09 Inhibition of [3H]dopamine uptake from wild type human DAT expressed in COS-7 ce... 38117239
Sodium-dependent dopamine transporter Ki = 2.53 nM 8.6 Displacement of [3H]WIN35,428 from DAT in Sprague-Dawley rat brain membranes inc... 27933960
Sodium-dependent dopamine transporter Ki = 2.53 nM 8.6 Dopamine Transporter Binding Assay: Brains from male Sprague-Dawley rats weighin... -
Sodium-dependent dopamine transporter Ki = 2.53 nM 8.6 Binding Assay: Dopamine Transporter Binding Assay. Brains from male Sprague-Dawl... -
Sodium-dependent dopamine transporter Ki = 2.53 nM 8.6 Dopamine Transporter Binding Assay: Dopamine Transporter Binding Assay. Brains f... -
Sodium-dependent dopamine transporter Ki = 2.6 nM 8.59 Displacement of [3H]WIN35428 from DAT in Sprague-Dawley rat striatal membranes i... 32947229
Sodium-dependent dopamine transporter Ki = 6.5 nM 8.19 Displacement of [3H]WIN35,428 from wild type human DAT expressed in COS7 cell me... 27933960
Sodium-dependent dopamine transporter Ki = 10.7 nM 7.97 Displacement of [3H]WIN35428 from wild type human DAT expressed in COS-7 cells i... 38117239
Sodium-dependent dopamine transporter Ki = 12.0 nM 7.92 Inhibition of DAT (unknown origin) expressed in COS7 cells assessed as reduction... 27933960
Sigma non-opioid intracellular receptor 1 Ki = 41.6 nM 7.38 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain co... 32947229
D(2) dopamine receptor Ki = 78.6 nM 7.11 Displacement of [3H]N-methylspiperone from human D2R expressed in HEK293 cell me... 27933960
D(2) dopamine receptor Ki = 78.6 nM 7.11 Displacement of [3H]-N-methylspiperone from human D2L receptor expressed in HEK2... 32947229
Unchecked Ki = 97.0 nM 7.01 Displacement of [3H]WIN35,428 from human DAT Y156F mutant expressed in COS7 cell... 27933960
Unchecked Ki = 116.0 nM 6.94 Displacement of [3H]WIN35428 from human DAT Y156F mutant expessed in COS-7 cells... 38117239
Unchecked Ki = 176.0 nM 6.75 Uptake Assays: The uptake assays were carried out 2 days after transfection. Pri... -
Unchecked Ki = 336.0 nM 6.47 Uptake Assays: The uptake assays were carried out 2 days after transfection. Pri... -
Sigma non-opioid intracellular receptor 1 Ki = 336.0 nM 6.47 Displacement of [3H](+)-pentazocine from sigma1 receptor in whole-guinea pig bra... 27933960
Unchecked Ki = 537.0 nM 6.27 Inhibition of [3H]dopamine uptake from human DAT Y335A mutant expressed in COS-7... 38117239
D(3) dopamine receptor Ki = 652.0 nM 6.19 Displacement of [3H]N-methylspiperone from human D3R expressed in HEK293 cell me... 27933960
D(3) dopamine receptor Ki = 652.0 nM 6.19 Displacement of [3H]-N-methylspiperone from human D3 receptor expressed in HEK29... 32947229

Literature References

PubMed DOI Target Context # Activities
27933960 10.1021/acs.jmedchem.6b01373 Unchecked 6
38117239 10.1021/acs.jmedchem.3c02037 Unchecked 4
27933960 10.1021/acs.jmedchem.6b01373 Sodium-dependent dopamine transporter 3
32947229 10.1016/j.ejmech.2020.112674 Unchecked 3
27933960 10.1021/acs.jmedchem.6b01373 ADMET 3
38117239 10.1021/acs.jmedchem.3c02037 ADMET 2
38117239 10.1021/acs.jmedchem.3c02037 Sodium-dependent dopamine transporter 2
27933960 10.1021/acs.jmedchem.6b01373 NON-PROTEIN TARGET 2
27933960 10.1021/acs.jmedchem.6b01373 D(2) dopamine receptor 2
27933960 10.1021/acs.jmedchem.6b01373 Sigma non-opioid intracellular receptor 1 1
32947229 10.1016/j.ejmech.2020.112674 Sodium-dependent dopamine transporter 1
32947229 10.1016/j.ejmech.2020.112674 Sodium-dependent serotonin transporter 1
32947229 10.1016/j.ejmech.2020.112674 Sigma non-opioid intracellular receptor 1 1
27933960 10.1021/acs.jmedchem.6b01373 D(4) dopamine receptor 1
32947229 10.1016/j.ejmech.2020.112674 D(2) dopamine receptor 1
32947229 10.1016/j.ejmech.2020.112674 D(3) dopamine receptor 1
32947229 10.1016/j.ejmech.2020.112674 D(4) dopamine receptor 1
27933960 10.1021/acs.jmedchem.6b01373 D(3) dopamine receptor 1
27933960 10.1021/acs.jmedchem.6b01373 Sodium-dependent serotonin transporter 1

Data from ChEMBL 36 via Core Engine