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Compound Detail

CHEMBL4206272

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CS(=O)(=O)N1CCN(C(=O)c2cnc3ccc(F)cc3c2-c2ccc(C3(C#N)CC3)cc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4206272
Phase Preclinical
Structure Type MOL
InChI Key WIXZFNIBMHEUJH-UHFFFAOYSA-N
3
Targets
15
Activities
3
Assay Types
21
PK Parameters
20
Publications
0
Known Names

Molecular Properties

478.6
MW (Da)
3.31
ALogP
5
HBA
0
HBD
94.4
PSA (Ų)
0.57
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H23FN4O3S
MW 478.55
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -1.52

Activity Summary

IC50 9 meas. best 8.15
EC50 4 meas. best 5.7
Ki 2 meas. best 8.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aldehyde dehydrogenase 1A1
CHEMBL3577
 IC50 8.15 6.9425 7.0 8
Aldehyde dehydrogenase 1A1
CHEMBL3577
 Ki 8.14 7.885 7.2 2
Aldehyde dehydrogenase 1A1
CHEMBL3577
 EC50 5.7 5.3 2000.0 3
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.96 4.96 10940.0 1
OV-90
CHEMBL4296481
 EC50 4.34 4.34 45600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1830.0 ng.hr.mL-1 Mus musculus
AUC 6980.0 ng.hr.mL-1 Mus musculus
AUC 3160.0 ng.hr.mL-1 Rattus norvegicus
AUC 7536.0 ng.hr.mL-1 Rattus norvegicus
CL 18.0 mL.min-1.kg-1 Mus musculus
CL 11.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 4173.02 nM Mus musculus
Cmax 3197.16 nM Mus musculus
Cmax 5405.91 nM Rattus norvegicus
Cmax 4137.5 nM Rattus norvegicus
F 76.0 % Mus musculus
F 48.0 % Rattus norvegicus
T1/2 0.5 hr Rattus norvegicus
T1/2 1.3 hr Mus musculus
T1/2 2.2 hr Mus musculus
T1/2 1.5 hr Rattus norvegicus
T1/2 3.5 hr Rattus norvegicus
T1/2 2.0 hr Mus musculus
T1/2 2.0 hr Homo sapiens
T1/2 2.0 hr Homo sapiens
T1/2 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aldehyde dehydrogenase 1A1 IC50 = 7.0 nM 8.15 Inhibition of human ALDH1A1 using NAD+/propionaldehyde as substrate/cofactor pre... 29767973
Aldehyde dehydrogenase 1A1 Ki = 7.2 nM 8.14 Inhibition of human ALDH1A1 using propionaldehyde as substrate and varied concen... 29767973
Aldehyde dehydrogenase 1A1 Ki = 23.3 nM 7.63 Inhibition of human ALDH1A1 using NAD+ as cofactor and varied concentration of p... 29767973
Aldehyde dehydrogenase 1A1 IC50 = 31.8 nM 7.5 Inhibition of ALDH1A1 in human SKOV3TR cells assessed as potentiation of paclita... 29767973
Aldehyde dehydrogenase 1A1 IC50 = 48.5 nM 7.31 Inhibition of human ALDH1A1 using all-trans-retinal as substrate preincubated fo... 29767973
Aldehyde dehydrogenase 1A1 IC50 = 77.0 nM 7.11 Inhibition of ALDH1A1 in human MIAPaCa2 cells after 30 mins by aldefluor assay 29767973
Aldehyde dehydrogenase 1A1 IC50 = 102.0 nM 6.99 Inhibition of ALDH1A1 in human SKOV3TR cells assessed as potentiation of paclita... 29767973
Aldehyde dehydrogenase 1A1 IC50 = 411.0 nM 6.39 Inhibition of ALDH1A1 in human SKOV3TR cells assessed as potentiation of paclita... 29767973
Aldehyde dehydrogenase 1A1 IC50 = 870.0 nM 6.06 Inhibition of ALDH1A1 in human SKOV3TR cells assessed as potentiation of paclita... 29767973
Aldehyde dehydrogenase 1A1 IC50 = 924.0 nM 6.03 Inhibition of ALDH1A1 in human SKOV3TR cells assessed as potentiation of paclita... 29767973
Aldehyde dehydrogenase 1A1 EC50 = 2000.0 nM 5.7 Stabilization of ALDH1A1 in human OV90 cells assessed as increase in melting tem... 29767973
Aldehyde dehydrogenase 1A1 EC50 = 5590.0 nM 5.25 Stabilization of ALDH1A1 in human OV90 cells assessed as increase in melting tem... 29767973
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 10940.0 nM 4.96 Inhibition of human ERG 29767973
Aldehyde dehydrogenase 1A1 EC50 = 11200.0 nM 4.95 Inhibition of ALDH1A1 in human SKOV3TR cells assessed as potentiation of 100 nM ... 29767973
OV-90 EC50 = 45600.0 nM 4.34 Cytotoxicity against 3D culture of human OV90 cells assessed as decrease in cell... 29767973

Literature References

PubMed DOI Target Context # Activities
29767973 10.1021/acs.jmedchem.8b00270 Aldehyde dehydrogenase 1A1 14
29767973 10.1021/acs.jmedchem.8b00270 Mus musculus 12
29767973 10.1021/acs.jmedchem.8b00270 ADMET 10
29767973 10.1021/acs.jmedchem.8b00270 Rattus norvegicus 9
33341649 10.1016/j.ejmech.2020.113060 Aldehyde dehydrogenase 1A1 3
29767973 10.1021/acs.jmedchem.8b00270 Unchecked 2
29767973 10.1021/acs.jmedchem.8b00270 Cytochrome P450 3A4 2
29767973 10.1021/acs.jmedchem.8b00270 Cytochrome P450 2C9 2
29767973 10.1021/acs.jmedchem.8b00270 Cytochrome P450 2D6 2
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
- 10.6019/CHEMBL5724796 Tyrosine-protein kinase ABL1 1
- 10.6019/CHEMBL5724796 Aurora kinase A 1
- 10.6019/CHEMBL5724796 Mitogen-activated protein kinase 1 1
- 10.6019/CHEMBL5724796 Glycogen synthase kinase-3 beta 1
- 10.6019/CHEMBL5724796 Cyclin-dependent kinase 2 1
- 10.6019/CHEMBL5724796 Casein kinase I isoform delta 1
33341649 10.1016/j.ejmech.2020.113060 SK-OV-3 1
33341649 10.1016/j.ejmech.2020.113060 Retinaldehyde dehydrogenase 3 1
29767973 10.1021/acs.jmedchem.8b00270 Voltage-gated inwardly rectifying potassium channel KCNH2 1
29767973 10.1021/acs.jmedchem.8b00270 No relevant target 1

Data from ChEMBL 36 via Core Engine