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Compound Detail

CHEMBL192046

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C[C@@]12OC(=O)[C@]1([C@@H](O)C1CCCCC1)NC(=O)[C@@H]2CCCl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL192046
Phase Preclinical
Structure Type MOL
InChI Key OJZFVOGTYOBPKD-GVARAGBVSA-N
6
Targets
9
Activities
2
Assay Types
0
PK Parameters
6
Publications
0
Known Names

Molecular Properties

315.8
MW (Da)
1.36
ALogP
4
HBA
2
HBD
75.6
PSA (Ų)
0.61
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 C15H22ClNO4
MW 315.80
Aromatic Rings 0
Heavy Atoms 21
NP-Likeness 1.99

Activity Summary

IC50 8 meas. best 7.7
EC50 1 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proteasome Macropain subunit MB1
CHEMBL4662
 EC50 8.0 8.0 10.0 1
Oryctolagus cuniculus
CHEMBL374
 IC50 7.7 6.7167 20.0 3
Proteasome Macropain subunit MB1
CHEMBL4662
 IC50 7.64 7.64 23.0 1
Unchecked
CHEMBL612545
 IC50 7.56 7.56 27.5 1
RPMI-8226
CHEMBL614882
 IC50 7.28 7.28 52.0 1
HEK293
CHEMBL614818
 IC50 7.15 7.15 71.0 1
HCT-116
CHEMBL394
 IC50 6.75 6.75 176.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proteasome Macropain subunit MB1 EC50 = 10.0 nM 8.0 Inhibition of chymotrypsin like activity of 20S proteasome in HEK293 cells after... 24269479
Oryctolagus cuniculus IC50 = 20.0 nM 7.7 Inhibition of chymotrypsin-like (CT-L) activity of rabbit 20S proteasome 15916417
Proteasome Macropain subunit MB1 IC50 = 23.0 nM 7.64 Inhibition of chymotrypsin like activity of human 20S proteasome after 1 hr by l... 24269479
Unchecked IC50 = 27.5 nM 7.56 Inhibition of chymotrypsin like activity of yeast 20S proteasome beta 5 subunit ... 19746976
RPMI-8226 IC50 = 52.0 nM 7.28 Cytotoxic activity against RPMI 8226 cells 15916417
HEK293 IC50 = 71.0 nM 7.15 Inhibition of NF-kB activation in HEK293 cells 15916417
HCT-116 IC50 = 176.0 nM 6.75 Cytotoxicity against human HCT116 cells after 72 hrs by MTS/PMS assay 19746976
Oryctolagus cuniculus IC50 = 250.0 nM 6.6 Inhibition of trypsin-like (T-L) activity of rabbit 20S proteasome 15916417
Oryctolagus cuniculus IC50 = 1400.0 nM 5.85 Inhibition of caspase-like (CA-L) activity of rabbit 20S proteasome 15916417

Literature References

PubMed DOI Target Context # Activities
24269479 10.1016/j.bmcl.2013.09.066 Proteasome Macropain subunit MB1 6
15916417 10.1021/jm048995+ Oryctolagus cuniculus 3
15916417 10.1021/jm048995+ RPMI-8226 1
15916417 10.1021/jm048995+ HEK293 1
19746976 10.1021/jm901098m Unchecked 1
19746976 10.1021/jm901098m HCT-116 1

Data from ChEMBL 36 via Core Engine