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Compound Detail

CHEMBL3134157

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Cc1cc(CS(=O)(=O)c2ccccc2)cc(OCc2ccc(CN3CCC[C@@H]3CO)cc2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3134157
Phase Preclinical
Structure Type MOL
InChI Key NPUXORBZRBIOMQ-RUZDIDTESA-N
8
Targets
37
Activities
3
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

465.6
MW (Da)
4.50
ALogP
5
HBA
1
HBD
66.8
PSA (Ų)
0.50
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H31NO4S
MW 465.62
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -1.11

Activity Summary

IC50 26 meas. best 9.1
Ki 10 meas. best 8.44
Kd 1 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sphingosine kinase 1
CHEMBL4394
 IC50 9.1 8.0127 0.8 15
Sphingosine kinase 1
CHEMBL2401605
 Ki 8.44 8.44 3.6 1
Sphingosine kinase 2
CHEMBL3023
 Ki 8.44 8.44 3.6 1
Sphingosine kinase 1
CHEMBL4394
 Ki 8.44 8.4263 3.6 8
Sphingosine kinase 1
CHEMBL4394
 Kd 8.3 8.3 5.0 1
Sphingosine kinase 2
CHEMBL3023
 IC50 6.45 5.95 356.0 6
HT-29
CHEMBL384
 IC50 4.88 4.88 13020.0 1
MCF7
CHEMBL387
 IC50 4.79 4.79 16230.0 1
MDA-MB-231
CHEMBL400
 IC50 4.57 4.57 27120.0 1
U-937
CHEMBL612794
 IC50 4.51 4.51 30720.0 1
MGC-803
CHEMBL3706566
 IC50 4.29 4.29 51660.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 32.3 ng.hr.mL-1 Mus musculus
AUC 168.0 ng.hr.mL-1 Mus musculus
CL 207.0 mL.min-1.kg-1 Mus musculus
Cmax 36.08 nM Mus musculus
F 1.92 % Mus musculus
T1/2 4.3 hr Mus musculus
T1/2 1.01 hr Mus musculus
T1/2 1.2 hr Mus musculus
Tmax 0.25 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sphingosine kinase 1 IC50 = 0.8 nM 9.1 Inhibition of SPHK1 in human MDA1483 cells using C17-sphingosine as substrate as... 28231433
Sphingosine kinase 1 IC50 = 2.0 nM 8.7 Inhibition of human C-terminal His6-tagged SPHK1 expressed in fall armyworm sf9 ... 28231433
Sphingosine kinase 1 IC50 = 2.6 nM 8.59 Inhibition of SPHK1 (unknown origin) using sphingosine-fluorescein as substrate ... 35439002
Sphingosine kinase 1 IC50 = 2.7 nM 8.57 Inhibition of human C-terminal His6-tagged SPHK1 expressed in fall armyworm sf9 ... 28231433
Sphingosine kinase 1 IC50 = 2.7 nM 8.57 Inhibition of recombinant C-terminal His6-tagged human SphK1 expressed in baculo... 28408190
Sphingosine kinase 1 IC50 = 2.7 nM 8.57 Inhibition of recombinant human C-terminus His-tagged SphK1 expressed in baculov... 33454547
Sphingosine kinase 1 IC50 = 3.0 nM 8.52 Inhibition of SK1 (unknown origin) using 3 uM of sphingosine as substrate 26780304
Sphingosine kinase 1 Ki = 3.6 nM 8.44 Inhibition of human recombinant SphK1 expressed in Sf9 cells assessed as radiola... 25643074
Sphingosine kinase 1 Ki = 3.6 nM 8.44 Inhibition of SphK1 in mouse erythrocytes using sphingosine as substrate by lumi... 26985306
Sphingosine kinase 1 Ki = 3.6 nM 8.44 Inhibition of recombinant human C-terminal His-tagged SPHK1 expressed in fall ar... 28406646
Sphingosine kinase 1 Ki = 3.6 nM 8.44 Inhibition of human C-terminal His6-tagged SphK1 expressed in baculovirus infect... 28822281
Sphingosine kinase 2 Ki = 3.6 nM 8.44 Inhibition of SK2 (unknown origin) 30889352
Sphingosine kinase 1 Ki = 3.6 nM 8.44 Inhibition of recombinant human SphK1 expressed in baculovirus infected Sf9 cell... 33385956
Sphingosine kinase 1 Ki = 3.6 nM 8.44 Competitive inhibition of recombinant human C-terminal His-tagged SphK1 expresse... 32919113
Sphingosine kinase 1 Ki = 3.6 nM 8.44 Competitive-inhibition of recombinant human C-terminal His6-tagged Sphk1 express... 33445156
Sphingosine kinase 1 IC50 = 3.6 nM 8.44 Inhibition of C-terminal His6-tagged human SPHK1 expressed in baculovirus infect... 35439002
Sphingosine kinase 1 Ki = 4.0 nM 8.4 Inhibition of SK1 (unknown origin) 26780304
Sphingosine kinase 1 Ki = 4.3 nM 8.37 Inhibition of His6 tagged human SphK1 expressed in Sf21 cells using FITC-sphingo... 25516793
Sphingosine kinase 1 Kd = 5.0 nM 8.3 Binding affinity to SK1 (unknown origin) assessed as inhibition of sphingosine p... 29969256
Sphingosine kinase 1 IC50 = 20.0 nM 7.7 Inhibition of SPHK1 in human whole-blood using C17-sphingosine as substrate asse... 28231433

Literature References

PubMed DOI Target Context # Activities
35439002 10.1021/acs.jmedchem.2c00040 MDA-MB-231 17
35439002 10.1021/acs.jmedchem.2c00040 HT-29 14
35439002 10.1021/acs.jmedchem.2c00040 ADMET 12
26780304 10.1021/acs.jmedchem.5b01439 Sphingosine kinase 1 5
30889352 10.1021/acs.jmedchem.9b00162 Sphingosine kinase 2 4
28231433 10.1021/acs.jmedchem.7b00070 Sphingosine kinase 1 4
26780304 10.1021/acs.jmedchem.5b01439 Sphingosine kinase 2 3
35439002 10.1021/acs.jmedchem.2c00040 Sphingosine kinase 1 3
32435405 10.1021/acsmedchemlett.9b00665 C2C12 3
35439002 10.1021/acs.jmedchem.2c00040 Sphingosine kinase 2 2
26985306 10.1021/acsmedchemlett.5b00304 Sphingosine kinase 1 2
24396570 10.1039/c3md00201b Sphingosine kinase 2 2
24396570 10.1039/c3md00201b Molecular identity unknown 2
24396570 10.1039/c3md00201b Sphingosine kinase 1 2
25516793 10.1021/ml5004074 Sphingosine kinase 1 1
25643074 10.1021/jm501760d Sphingosine kinase 1 1
25516793 10.1021/ml5004074 Unchecked 1
26780304 10.1021/acs.jmedchem.5b01439 NON-PROTEIN TARGET 1
26780304 10.1021/acs.jmedchem.5b01439 HEK293 1
28231433 10.1021/acs.jmedchem.7b00070 Unchecked 1

Data from ChEMBL 36 via Core Engine