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Compound Detail

CHEMBL3741589

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O=C(O)C1CN(Cc2ccc(OCc3ccc(Cl)c(Cl)c3)cc2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3741589
Phase Preclinical
Structure Type MOL
InChI Key WAAWETUDFSIYSD-UHFFFAOYSA-N
5
Targets
9
Activities
3
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

366.2
MW (Da)
4.09
ALogP
3
HBA
1
HBD
49.8
PSA (Ų)
0.84
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H17Cl2NO3
MW 366.24
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -1.11

Activity Summary

IC50 4 meas. best 8.22
EC50 3 meas. best 8.39
Ki 2 meas. best 6.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sphingosine 1-phosphate receptor 5
CHEMBL2274
 EC50 8.39 8.315 4.1 2
Sphingosine 1-phosphate receptor 5
CHEMBL2274
 IC50 8.22 8.22 6.0 1
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 IC50 6.44 6.44 362.0 2
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 EC50 6.4 6.4 398.1 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 6.31 6.31 487.5 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 5.34 5.34 4606.3 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.11 4.11 77000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 35000.0 ng.hr.mL-1 Mus musculus
AUC 43000.0 ng.hr.mL-1 Rattus norvegicus
AUC 670000.0 ng.hr.mL-1 Rattus norvegicus
AUC 8500.0 ng.hr.mL-1 Mus musculus
AUC 3200.0 ng.hr.mL-1 Mus musculus
AUC 6400.0 ng.hr.mL-1 Rattus norvegicus
AUC - - Rattus norvegicus
AUC 12000.0 ng.hr.mL-1 Canis lupus familiaris
AUC 6400.0 ng.hr.mL-1 Macaca fascicularis
AUC 4800.0 ng.hr.mL-1 Mus musculus
AUC 1600.0 ng.hr.mL-1 Mus musculus
AUC 8700.0 ng.hr.mL-1 Rattus norvegicus
AUC 3100.0 ng.hr.mL-1 Rattus norvegicus
AUC 11000.0 ng.hr.mL-1 Canis lupus familiaris
AUC 5500.0 ng.hr.mL-1 Macaca fascicularis
CL 4.0 mL.min-1.kg-1 Mus musculus
CL - - Mus musculus
CL 2.667 mL.min-1.kg-1 Rattus norvegicus
CL - - Rattus norvegicus
CL 1.5 mL.min-1.kg-1 Canis lupus familiaris
CL 2.667 mL.min-1.kg-1 Macaca fascicularis
Cmax 6826.12 nM Mus musculus
Cmax 819.13 nM Mus musculus
Cmax 117.41 nM Mus musculus
Cmax 1092.18 nM Rattus norvegicus
Cmax 327.65 nM Rattus norvegicus
Cmax 1884.01 nM Canis lupus familiaris
Cmax 1774.79 nM Macaca fascicularis
Cmax 363149847.09 nM Mus musculus
F 57.0 % Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sphingosine 1-phosphate receptor 5 EC50 = 4.1 nM 8.39 Agonist activity at S1P5 receptor (unknown origin) expressed in CHO cells assess... 26509640
Sphingosine 1-phosphate receptor 5 EC50 = 5.7 nM 8.24 Agonist activity at S1P5 receptor (unknown origin) expressed in CHO cell membran... 26509640
Sphingosine 1-phosphate receptor 5 IC50 = 6.0 nM 8.22 Displacement of [33P]S1P from S1P5 receptor (unknown origin) expressed in HEK ce... 26509640
Sphingosine 1-phosphate receptor 1 IC50 = 362.0 nM 6.44 Displacement of [33P]S1P from S1P1 receptor (unknown origin) expressed in HEK ce... 26509640
Sphingosine 1-phosphate receptor 1 IC50 = 362.0 nM 6.44 Agonist activity at S1P1 receptor (unknown origin) expressed in CHO cell membran... 26509640
Sphingosine 1-phosphate receptor 1 EC50 = 398.11 nM 6.4 Modulation of S1PR1 (unknown origin) 36758307
Sigma non-opioid intracellular receptor 1 Ki = 487.52 nM 6.31 PDSP Secondary Binding target: SIGMAR1 - Compounds are tested at 10 uM concentra... -
5-hydroxytryptamine receptor 2A Ki = 4606.27 nM 5.34 PDSP Secondary Binding target: HTR2A - Compounds are tested at 10 uM concentrati... -
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 77000.0 nM 4.11 Displacement of doferilide from human ERG 26509640

Literature References

PubMed DOI Target Context # Activities
26509640 10.1021/acs.jmedchem.5b00928 Plasma 44
- 10.6019/CHEMBL5724696 U2OS 24
26509640 10.1021/acs.jmedchem.5b00928 Brain 21
26509640 10.1021/acs.jmedchem.5b00928 Rattus norvegicus 18
- 10.6019/CHEMBL5724696 TERT-RPE1 12
26509640 10.1021/acs.jmedchem.5b00928 Mus musculus 10
- 10.6019/CHEMBL4689842 HEK-293T 9
- 10.6019/CHEMBL4689842 Fibroblast 9
- 10.6019/CHEMBL4689842 U2OS 8
26509640 10.1021/acs.jmedchem.5b00928 Unchecked 7
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
26509640 10.1021/acs.jmedchem.5b00928 Molecular identity unknown 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5

Data from ChEMBL 36 via Core Engine