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Compound Detail

CHEMBL4290574

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CC(O)[C@@H](NC(=O)c1ccc(OCc2ccccc2)cc1)C(=O)N[C@@H](C[C@]1(O)C(=O)Nc2ccccc21)C(=O)NCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4290574
Phase Preclinical
Structure Type MOL
InChI Key KYPGRKXNTMUUDH-ZTOUSHPOSA-N
12
Targets
12
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

636.7
MW (Da)
2.78
ALogP
7
HBA
6
HBD
166.1
PSA (Ų)
0.13
QED
2
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C36H36N4O7
MW 636.71
Aromatic Rings 4
Heavy Atoms 47
NP-Likeness -0.17

Activity Summary

EC50 6 meas. best 6.7
IC50 6 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proteasome Macropain subunit MB1
CHEMBL4662
 IC50 8.15 8.15 7.1 1
Proteasome subunit beta type-8
CHEMBL5620
 IC50 7.99 7.99 10.2 1
HCT-116
CHEMBL394
 EC50 6.7 6.7 200.0 1
PC-3
CHEMBL390
 EC50 6.4 6.4 400.0 1
MCF7
CHEMBL387
 EC50 6.16 6.16 700.0 1
MDA-MB-231
CHEMBL400
 EC50 6.16 6.16 700.0 1
NCI-H727
CHEMBL1075545
 EC50 5.7 5.7 2000.0 1
Caco-2
CHEMBL614058
 EC50 5.3 5.3 5000.0 1
Proteasome subunit beta type-10
CHEMBL3317334
 IC50 5.18 5.18 6600.0 1
Proteasome Macropain subunit
CHEMBL3492
 IC50 4.88 4.88 13200.0 1
Proteasome subunit beta type-9
CHEMBL1944495
 IC50 4.62 4.62 23800.0 1
Proteasome component C5
CHEMBL4208
 IC50 4.5 4.5 31900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proteasome Macropain subunit MB1 IC50 = 7.1 nM 8.15 Inhibition of human 20S constitutive proteasome beta-5 using Suc-LLVY-AMC as sub... 29339252
Proteasome subunit beta type-8 IC50 = 10.2 nM 7.99 Inhibition of human 20S immunoproteasome beta-5 using Suc-LLVY-AMC as substrate ... 29339252
HCT-116 EC50 = 200.0 nM 6.7 Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ... 29339252
PC-3 EC50 = 400.0 nM 6.4 Cytotoxicity against human PC3 cells assessed as reduction in cell viability aft... 29339252
MDA-MB-231 EC50 = 700.0 nM 6.16 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 29339252
MCF7 EC50 = 700.0 nM 6.16 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability af... 29339252
NCI-H727 EC50 = 2000.0 nM 5.7 Cytotoxicity against human NCI-H727 cells assessed as reduction in cell viabilit... 29339252
Caco-2 EC50 = 5000.0 nM 5.3 Cytotoxicity against human Caco2 cells assessed as reduction in cell viability a... 29339252
Proteasome subunit beta type-10 IC50 = 6600.0 nM 5.18 Inhibition of human 20S immunoproteasome beta-2 using BocLRR-AMC as substrate in... 29339252
Proteasome Macropain subunit IC50 = 13200.0 nM 4.88 Inhibition of human 20S constitutive proteasome beta-2 using BocLRR-AMC as subst... 29339252
Proteasome subunit beta type-9 IC50 = 23800.0 nM 4.62 Inhibition of human 20S immunoproteasome beta-1 using Ac-PAL-AMC as substrate in... 29339252
Proteasome component C5 IC50 = 31900.0 nM 4.5 Inhibition of human 20S constitutive proteasome beta-1 using Z-LLE-betaNA as sub... 29339252

Literature References

PubMed DOI Target Context # Activities
29339252 10.1016/j.ejmech.2018.01.013 Proteasome Macropain subunit MB1 3
29339252 10.1016/j.ejmech.2018.01.013 Proteasome subunit beta type-8 3
29339252 10.1016/j.ejmech.2018.01.013 Proteasome component C5 2
29339252 10.1016/j.ejmech.2018.01.013 Proteasome subunit beta type-9 2
29339252 10.1016/j.ejmech.2018.01.013 Proteasome Macropain subunit 2
29339252 10.1016/j.ejmech.2018.01.013 Proteasome subunit beta type-10 2
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