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Compound Detail

CHEMBL5558191

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COC(=O)c1ccc2[nH]cc(C(=O)C(=O)NC3CCN(c4ccc(C)cc4Cl)C3=O)c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5558191
Phase Preclinical
Structure Type MOL
InChI Key ZSATYRRCVARMFY-UHFFFAOYSA-N
26
Targets
31
Activities
2
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

453.9
MW (Da)
3.02
ALogP
5
HBA
2
HBD
108.6
PSA (Ų)
0.35
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H20ClN3O5
MW 453.88
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.05

Activity Summary

IC50 29 meas. best 5.33
Kd 2 meas. best 5.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Beta-1,3-glucuronyltransferase 3
CHEMBL3958
 Kd 5.4 5.29 3962.0 2
HT-29
CHEMBL384
 IC50 5.33 5.33 4710.0 1
AGS
CHEMBL613860
 IC50 5.27 5.27 5330.0 1
U-937
CHEMBL612794
 IC50 5.22 5.22 5990.0 1
U-251
CHEMBL615022
 IC50 5.21 5.21 6160.0 1
Hepa 1-6
CHEMBL6066745
 IC50 5.21 5.21 6220.0 1
HCCLM3
CHEMBL5465453
 IC50 5.21 4.975 6220.0 2
PLC-PRF-5
CHEMBL1075561
 IC50 5.19 5.19 6520.0 1
MHCC97H
CHEMBL4296470
 IC50 5.18 4.9575 6530.0 4
H4
CHEMBL1075452
 IC50 5.18 5.18 6650.0 1
Jurkat
CHEMBL397
 IC50 5.17 5.17 6690.0 1
K562
CHEMBL385
 IC50 5.08 5.08 8250.0 1
SW-620
CHEMBL612262
 IC50 5.06 5.06 8660.0 1
MEG-01
CHEMBL2366084
 IC50 4.94 4.94 11480.0 1
NCI-H446
CHEMBL612440
 IC50 4.94 4.94 11580.0 1
SNU-387
CHEMBL1075583
 IC50 4.93 4.93 11710.0 1
MDA-MB-231
CHEMBL400
 IC50 4.91 4.91 12320.0 1
Hep 3B2
CHEMBL4296437
 IC50 4.91 4.91 12190.0 1
Huh-7
CHEMBL614039
 IC50 4.9 4.9 12540.0 1
PC-3
CHEMBL390
 IC50 4.86 4.86 13700.0 1
MKN-45
CHEMBL614354
 IC50 4.86 4.86 13870.0 1
NCI-H1650
CHEMBL1075518
 IC50 4.67 4.67 21560.0 1
THP-1
CHEMBL614245
 IC50 4.62 4.62 23910.0 1
Calu-3
CHEMBL614534
 IC50 4.38 4.38 41640.0 1
HCC1937
CHEMBL1075458
 IC50 4.32 4.32 47890.0 1
SK-OV-3
CHEMBL614925
 IC50 4.01 4.01 98740.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1854.98 ng.hr.mL-1 Mus musculus
AUC 9515.96 ng.hr.mL-1 Mus musculus
CL 0.01 mL.min-1.kg-1 Mus musculus
CL 0.02 mL.min-1.kg-1 Mus musculus
Cmax 3.35 ug.mL-1 Mus musculus
Cmax 9.135 ug.mL-1 Mus musculus
F 66.37 % Mus musculus
T1/2 0.2838 hr Homo sapiens
T1/2 0.431 hr Rattus norvegicus
T1/2 0.6312 hr Mus musculus
T1/2 0.77 hr Mus musculus
T1/2 4.18 hr Mus musculus
Tmax 0.08 hr Mus musculus
Tmax 0.22 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Beta-1,3-glucuronyltransferase 3 Kd = 3962.0 nM 5.4 Binding affinity to CM5 sensor chip immobilized human B3GAT3 assessed as dissoci... 38919032
HT-29 IC50 = 4710.0 nM 5.33 Anti-tumor activity against human HT-29 cells assessed as inhibition of cell gro... 38919032
AGS IC50 = 5330.0 nM 5.27 Anti-tumor activity against human AGS cells assessed as inhibition of cell growt... 38919032
U-937 IC50 = 5990.0 nM 5.22 Anti-tumor activity against human U-937 cells assessed as inhibition of cell gro... 38919032
HCCLM3 IC50 = 6220.0 nM 5.21 Antitumor activity against human HCCLM3 cells assessed as inhibition of cell gro... 38919032
Hepa 1-6 IC50 = 6220.0 nM 5.21 Antitumor activity against mouse Hepa1-6 cells assessed as inhibition of cell pr... 38919032
U-251 IC50 = 6160.0 nM 5.21 Anti-tumor activity against human U-251MG cells assessed as inhibition of cell g... 38919032
PLC-PRF-5 IC50 = 6520.0 nM 5.19 Antitumor activity against human PLC-PRF-5 cells assessed as inhibition of cell ... 38919032
Beta-1,3-glucuronyltransferase 3 Kd = 6619.0 nM 5.18 Binding affinity to biotinylated B3GAT3 (unknown origin) assessed as dissociatio... 38919032
MHCC97H IC50 = 6530.0 nM 5.18 Antitumor activity against human MHCC97H cells assessed as inhibition of cell gr... 38919032
H4 IC50 = 6650.0 nM 5.18 Anti-tumor activity against human H4 cells assessed as inhibition of cell growth... 38919032
Jurkat IC50 = 6690.0 nM 5.17 Anti-tumor activity against human Jurkat cells assessed as inhibition of cell gr... 38919032
MHCC97H IC50 = 6920.0 nM 5.16 Cytotoxicity against (shRNA)-Ctrl transfected human MHCC97H cells assessed as ce... 38919032
K562 IC50 = 8250.0 nM 5.08 Anti-tumor activity against human K562 cells assessed as inhibition of cell grow... 38919032
SW-620 IC50 = 8660.0 nM 5.06 Anti-tumor activity against human SW620 cells assessed as inhibition of cell gro... 38919032
MEG-01 IC50 = 11480.0 nM 4.94 Anti-tumor activity against human MEG-01 cells assessed as inhibition of cell gr... 38919032
NCI-H446 IC50 = 11580.0 nM 4.94 Anti-tumor activity against human NCI-H446 cells assessed as inhibition of cell ... 38919032
SNU-387 IC50 = 11710.0 nM 4.93 Antitumor activity against human SNU-387 cells assessed as inhibition of cell pr... 38919032
Hep 3B2 IC50 = 12190.0 nM 4.91 Antitumor activity against human Hep3B cells assessed as inhibition of cell prol... 38919032
MDA-MB-231 IC50 = 12320.0 nM 4.91 Anti-tumor activity against human MDA-M8-231 cells assessed as inhibition of cel... 38919032

Literature References

PubMed DOI Target Context # Activities
38919032 10.1021/acs.jmedchem.4c00242 ADMET 36
38919032 10.1021/acs.jmedchem.4c00242 MHCC97H 29
38919032 10.1021/acs.jmedchem.4c00242 HCCLM3 22
38919032 10.1021/acs.jmedchem.4c00242 Unchecked 14
38919032 10.1021/acs.jmedchem.4c00242 Beta-1,3-glucuronyltransferase 3 4
38919032 10.1021/acs.jmedchem.4c00242 Huh-7 1
38919032 10.1021/acs.jmedchem.4c00242 Hep 3B2 1
38919032 10.1021/acs.jmedchem.4c00242 SNU-387 1
38919032 10.1021/acs.jmedchem.4c00242 PLC-PRF-5 1
38919032 10.1021/acs.jmedchem.4c00242 Hepa 1-6 1
38919032 10.1021/acs.jmedchem.4c00242 NCI-H446 1
38919032 10.1021/acs.jmedchem.4c00242 NCI-H1650 1
38919032 10.1021/acs.jmedchem.4c00242 Calu-3 1
38919032 10.1021/acs.jmedchem.4c00242 PC-3 1
38919032 10.1021/acs.jmedchem.4c00242 SK-OV-3 1
38919032 10.1021/acs.jmedchem.4c00242 AGS 1
38919032 10.1021/acs.jmedchem.4c00242 MKN-45 1
38919032 10.1021/acs.jmedchem.4c00242 HT-29 1
38919032 10.1021/acs.jmedchem.4c00242 SW-620 1
38919032 10.1021/acs.jmedchem.4c00242 MDA-MB-231 1

Data from ChEMBL 36 via Core Engine