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Compound Detail

CHEMBL553939

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CC1(C)CC(=O)c2c(C(F)(F)F)nn(-c3ccc(C(N)=O)c(N[C@H]4CC[C@H](OC(=O)CN)CC4)c3)c2C1.CS(=O)(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL553939
Phase Preclinical
Structure Type MOL
InChI Key NVGFSTMGRRADRG-IOJSEOPQSA-N
Parent Compound CHEMBL1195136
Active Moiety CHEMBL560895
13
Targets
16
Activities
2
Assay Types
16
PK Parameters
15
Publications
0
Known Names

Molecular Properties

521.5
MW (Da)
3.37
ALogP
8
HBA
3
HBD
142.3
PSA (Ų)
0.49
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C26H34F3N5O7S
MW 617.65
Aromatic Rings 2
Heavy Atoms 37
NP-Likeness -0.81

Activity Summary

IC50 15 meas. best 7.96
Kd 1 meas. best 7.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Heat shock protein HSP90
CHEMBL2095165
 IC50 7.96 7.09 11.0 4
MCF7
CHEMBL387
 IC50 7.8 7.8 16.0 1
SW-620
CHEMBL612262
 IC50 7.72 7.72 19.0 1
K562
CHEMBL385
 IC50 7.64 7.64 23.0 1
SK-MEL-5
CHEMBL614922
 IC50 7.6 7.6 25.0 1
LNCaP
CHEMBL612518
 IC50 7.51 7.51 31.0 1
HT-29
CHEMBL384
 IC50 7.5 7.5 32.0 1
MDA-MB-231
CHEMBL400
 IC50 7.42 7.42 38.0 1
Unchecked
CHEMBL612545
 Kd 7.39 7.39 41.0 1
A-375
CHEMBL613859
 IC50 7.29 7.29 51.0 1
PC-3
CHEMBL390
 IC50 6.94 6.94 114.0 1
HCT-15
CHEMBL612263
 IC50 6.72 6.72 190.0 1
NCI-H460
CHEMBL396
 IC50 6.67 6.67 215.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4869.0 ng.hr.mL-1 Mus musculus
AUC 3968.0 ng.hr.mL-1 Mus musculus
AUC 11004.0 ng.hr.mL-1 Mus musculus
AUC 25153.0 ng.hr.mL-1 Mus musculus
Cmax 8542.01 nM Mus musculus
Cmax 1432.3 nM Mus musculus
Cmax 4118.57 nM Mus musculus
Cmax 7698.35 nM Mus musculus
T1/2 2.6 hr Mus musculus
T1/2 2.5 hr Mus musculus
T1/2 2.9 hr Mus musculus
T1/2 3.3 hr Mus musculus
Tmax 0.083 hr Mus musculus
Tmax 1.0 hr Mus musculus
Tmax 1.0 hr Mus musculus
Tmax 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Heat shock protein HSP90 IC50 = 11.0 nM 7.96 Inhibition of Hsp90 in human AU565 cells assessed as pERK degradation after 24 h... 19552433
Heat shock protein HSP90 IC50 = 13.0 nM 7.89 Inhibition of Hsp90 in human A375 cells assessed as Hsp70 induction after 24 hrs... 19552433
MCF7 IC50 = 16.0 nM 7.8 Antiproliferative activity against human MCF7 cells after 72 to 144 hrs by cyqua... 19552433
SW-620 IC50 = 19.0 nM 7.72 Antiproliferative activity against human SW620 cells after 72 to 144 hrs by cyqu... 19552433
K562 IC50 = 23.0 nM 7.64 Antiproliferative activity against human K562 cells after 72 to 144 hrs by cyqua... 19552433
SK-MEL-5 IC50 = 25.0 nM 7.6 Antiproliferative activity against human SK-MEL-5 cells after 72 to 144 hrs by c... 19552433
LNCaP IC50 = 31.0 nM 7.51 Antiproliferative activity against human LNCAP cells after 72 to 144 hrs by cyqu... 19552433
HT-29 IC50 = 32.0 nM 7.5 Antiproliferative activity against human HT-29 cells after 72 to 144 hrs by cyqu... 19552433
MDA-MB-231 IC50 = 38.0 nM 7.42 Antiproliferative activity against human MDA-MB-231 cells after 72 to 144 hrs by... 19552433
Unchecked Kd = 41.0 nM 7.39 Binding affinity to pig spleen Hsp90 ATPase pocket by Bradford assay 19552433
A-375 IC50 = 51.0 nM 7.29 Antiproliferative activity against human A375 cells after 72 to 144 hrs by cyqua... 19552433
Heat shock protein HSP90 IC50 = 61.0 nM 7.21 Inhibition of Hsp90 in human A375 cells assessed as pS6 degradation after 24 hrs... 19552433
PC-3 IC50 = 114.0 nM 6.94 Antiproliferative activity against human PC3 cells after 72 to 144 hrs by cyquan... 19552433
HCT-15 IC50 = 190.0 nM 6.72 Antiproliferative activity against human HCT15 cells after 72 to 144 hrs by cyqu... 19552433
NCI-H460 IC50 = 215.0 nM 6.67 Antiproliferative activity against human NCI-H460 cells after 72 to 144 hrs by c... 19552433
Heat shock protein HSP90 IC50 = 5000.0 nM 5.3 Inhibition of Hsp90 in human AU565 cells assessed as Her2 degradation after 24 h... 19552433

Literature References

PubMed DOI Target Context # Activities
19552433 10.1021/jm900230j Mus musculus 26
19552433 10.1021/jm900230j Heat shock protein HSP90 4
19552433 10.1021/jm900230j HT-29 4
19552433 10.1021/jm900230j Unchecked 1
19552433 10.1021/jm900230j A-375 1
19552433 10.1021/jm900230j LNCaP 1
19552433 10.1021/jm900230j MCF7 1
19552433 10.1021/jm900230j SW-620 1
19552433 10.1021/jm900230j SK-MEL-5 1
19552433 10.1021/jm900230j PC-3 1
19552433 10.1021/jm900230j MDA-MB-231 1
19552433 10.1021/jm900230j NCI-H460 1
19552433 10.1021/jm900230j HCT-15 1
19552433 10.1021/jm900230j K562 1
19552433 10.1021/jm900230j No relevant target 1

Data from ChEMBL 36 via Core Engine