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Compound Detail

CHEMBL2337849

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C[C@H](NC(=O)[C@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)OC(C)(C)C)C(=O)N[C@@H](C[C@]1(O)C(=O)Nc2ccccc21)C(=O)NCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2337849
Phase Preclinical
Structure Type MOL
InChI Key LEFDHTPNDGQXKD-KUNNGYQLSA-N
7
Targets
16
Activities
3
Assay Types
1
PK Parameters
16
Publications
0
Known Names

Molecular Properties

749.9
MW (Da)
4.24
ALogP
8
HBA
6
HBD
184.2
PSA (Ų)
0.10
QED
2
Ro5 Violations
15
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C42H47N5O8
MW 749.87
Aromatic Rings 4
Heavy Atoms 55
NP-Likeness -0.24

Activity Summary

IC50 12 meas. best 5.82
EC50 2 meas. best 4.58
Ki 2 meas. best 5.61

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proteasome Macropain subunit PRE2
CHEMBL4659
 IC50 5.82 5.82 1500.0 1
Proteasome Macropain subunit MB1
CHEMBL4662
 Ki 5.61 5.455 2430.0 2
Unchecked
CHEMBL612545
 IC50 5.6 5.16 2530.0 6
Proteasome Macropain subunit MB1
CHEMBL4662
 IC50 5.5 5.3 3190.0 2
Proteasome Macropain subunit
CHEMBL3492
 IC50 5.14 5.14 7160.0 1
Proteasome component C5
CHEMBL4208
 IC50 4.94 4.87 11520.0 2
MCF7
CHEMBL387
 EC50 4.58 4.58 26000.0 1
HCT-116
CHEMBL394
 EC50 4.5 4.5 32000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 50.0 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proteasome Macropain subunit PRE2 IC50 = 1500.0 nM 5.82 Inhibition of chymotrypsin-like activity of yeast 20S proteasome beta-5 subunit ... 23540790
Proteasome Macropain subunit MB1 Ki = 2430.0 nM 5.61 Mixed type inhibition of chymotrypsin-like activity of human constitutive 20s pr... 23540790
Unchecked IC50 = 2530.0 nM 5.6 Inhibition of chymotrypsin-like activity of human inducible 20S immunoproteasome... 25333324
Proteasome Macropain subunit MB1 IC50 = 3190.0 nM 5.5 Inhibition of chymotrypsin-like activity of human constitutive 20s proteasome be... 23540790
Unchecked IC50 = 3200.0 nM 5.5 Inhibition of chymotrypsin-like activity of human constitutive 20S proteasome in... 25333324
Proteasome Macropain subunit MB1 Ki = 5030.0 nM 5.3 Mixed type inhibition of chymotrypsin-like activity of human constitutive 20s pr... 23540790
Unchecked IC50 = 6160.0 nM 5.21 Inhibition of PA activity of human inducible 20S immunoproteasome incubated for ... 25333324
Unchecked IC50 = 7100.0 nM 5.15 Inhibition of trypsin-like activity of human constitutive 20S proteasome incubat... 25333324
Proteasome Macropain subunit IC50 = 7160.0 nM 5.14 Inhibition of trypsin-like activity of human constitutive 20s proteasome beta-2 ... 23540790
Proteasome Macropain subunit MB1 IC50 = 7970.0 nM 5.1 Inhibition of chymotrypsin-like activity of proteasome beta-5 subunit in HEK293 ... 23540790
Proteasome component C5 IC50 = 11520.0 nM 4.94 Inhibition of postacid activity of human constitutive 20s proteasome beta-1 subu... 23540790
Unchecked IC50 = 11500.0 nM 4.94 Inhibition of PA activity of human constitutive 20S proteasome incubated for 15 ... 25333324
Proteasome component C5 IC50 = 16000.0 nM 4.8 Inhibition of postacid activity of 20s proteasome beta-1 subunit in HEK293 cells... 23540790
MCF7 EC50 = 26000.0 nM 4.58 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability af... 29339252
Unchecked IC50 = 27700.0 nM 4.56 Inhibition of trypsin-like activity of human inducible 20S immunoproteasome incu... 25333324
HCT-116 EC50 = 32000.0 nM 4.5 Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ... 29339252

Literature References

PubMed DOI Target Context # Activities
25333324 10.1021/jm5011429 Unchecked 6
23540790 10.1021/jm4002007 Proteasome Macropain subunit MB1 4
23540790 10.1021/jm4002007 Proteasome component C5 2
23540790 10.1021/jm4002007 Proteasome Macropain subunit PRE2 1
23540790 10.1021/jm4002007 No relevant target 1
23540790 10.1021/jm4002007 Cathepsin B 1
23540790 10.1021/jm4002007 Calpain-1 catalytic subunit 1
23540790 10.1021/jm4002007 Proteasome Macropain subunit 1
29339252 10.1016/j.ejmech.2018.01.013 Huh-7 1
29339252 10.1016/j.ejmech.2018.01.013 Caco-2 1
29339252 10.1016/j.ejmech.2018.01.013 MDA-MB-231 1
29339252 10.1016/j.ejmech.2018.01.013 HCT-116 1
29339252 10.1016/j.ejmech.2018.01.013 PC-3 1
29339252 10.1016/j.ejmech.2018.01.013 NCI-H727 1
29339252 10.1016/j.ejmech.2018.01.013 MCF7 1
29339252 10.1016/j.ejmech.2018.01.013 Fibroblast 1

Data from ChEMBL 36 via Core Engine