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Compound Detail

CHEMBL3237875

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COc1ccc(C[C@H](NC(=O)[C@H](C)NC(=O)CN2CCOCC2)C(=O)N[C@@H](Cc2ccccc2)C(=O)[C@@]2(C)CO2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3237875
Phase Preclinical
Structure Type BOTH
InChI Key WQAVPPWWLLVGFK-VTNASVEKSA-N
23
Targets
62
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

580.7
MW (Da)
0.64
ALogP
8
HBA
3
HBD
138.6
PSA (Ų)
0.28
QED
1
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C31H40N4O7
MW 580.68
Aromatic Rings 2
Heavy Atoms 42
NP-Likeness -0.45

Activity Summary

IC50 54 meas. best 8.24
EC50 8 meas. best 6.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proteasome subunit beta type-8
CHEMBL5620
 IC50 8.24 7.402 5.7 10
Unchecked
CHEMBL612545
 IC50 7.27 6.2267 54.0 9
Proteasome subunit beta type-8
CHEMBL1944492
 IC50 7.01 7.01 98.0 1
HCT-116
CHEMBL394
 EC50 6.96 6.96 110.0 1
PBMC
CHEMBL613107
 IC50 6.92 6.2443 120.0 7
Proteasome Macropain subunit MB1
CHEMBL4662
 IC50 6.82 6.458 150.0 5
Fibroblast
CHEMBL5314315
 EC50 6.8 6.8 160.0 1
MM1.S
CHEMBL4296471
 IC50 6.62 6.62 240.0 1
MCF7
CHEMBL387
 EC50 6.58 6.58 260.0 1
MDA-MB-231
CHEMBL400
 EC50 6.57 6.57 270.0 1
Proteasome subunit beta type-9
CHEMBL1944495
 IC50 6.54 6.2129 287.0 7
NCI-H727
CHEMBL1075545
 EC50 6.52 6.52 300.0 1
Proteasome subunit beta type-9
CHEMBL1944491
 IC50 6.48 6.48 328.0 1
PC-3
CHEMBL390
 EC50 6.48 6.48 330.0 1
Huh-7
CHEMBL614039
 EC50 6.41 6.41 390.0 1
Proteasome subunit beta type-5
CHEMBL1944494
 IC50 6.4 6.4 401.0 1
Proteasome subunit beta type-10
CHEMBL3317334
 IC50 6.23 5.97 590.0 5
RPMI-8226
CHEMBL614882
 IC50 6.17 6.17 680.0 1
Proteasome subunit beta type-10
CHEMBL4523133
 IC50 6.16 6.16 699.0 1
Proteasome subunit beta type-2
CHEMBL3112378
 IC50 6.04 6.04 913.0 1
Proteasome Macropain subunit
CHEMBL3492
 IC50 6.03 5.7967 927.0 3
Caco-2
CHEMBL614058
 EC50 5.89 5.89 1300.0 1
Proteasome component C5
CHEMBL4208
 IC50 4.66 4.66 22000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proteasome subunit beta type-8 IC50 = 5.7 nM 8.24 Inhibition of proteasome subunit beta-5i in human Raji cells using BODIPY-NC005 ... 25006746
Proteasome subunit beta type-8 IC50 = 18.0 nM 7.75 Inhibition of proteasome subunit beta-5i in human RPMI8226 cells using BODIPY-NC... 25006746
Proteasome subunit beta type-8 IC50 = 30.5 nM 7.52 Inhibition of human proteasome subunit beta-5i chymotrypsin like activity using ... 34087498
Proteasome subunit beta type-8 IC50 = 37.9 nM 7.42 Inhibition of LMP7 in human 20S immunoproteasome using Ac-ANW-AMC as substrate a... 32189500
Proteasome subunit beta type-8 IC50 = 39.0 nM 7.41 Inhibition of proteasome subunit beta-5i (unknown origin) 34087498
Proteasome subunit beta type-8 IC50 = 39.0 nM 7.41 Inhibition of LMP7 in human MOLT4 cells by ELISA 30380863
Proteasome subunit beta type-8 IC50 = 39.0 nM 7.41 Inhibition of LMP7 in human MOLT4 cell lysate after 1 hr by ELISA 28435528
Proteasome subunit beta type-8 IC50 = 52.0 nM 7.28 Inhibition of human 20S immunoproteasome beta-5 using Suc-LLVY-AMC as substrate ... 29339252
Unchecked IC50 = 54.0 nM 7.27 Inhibition of 20s proteasome subunit beta-5c in human Raji cells using BODIPY-NC... 25006746
Proteasome subunit beta type-8 IC50 = 58.5 nM 7.23 Inhibition of 20S immunoproteasome beta 5 chymotrypsin-like activity in human H2... 33639344
Proteasome subunit beta type-8 IC50 = 98.0 nM 7.01 Inhibition of LMP7 in mouse A20 cells by ELISA 30380863
HCT-116 EC50 = 110.0 nM 6.96 Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ... 29339252
PBMC IC50 = 120.0 nM 6.92 Anti-inflammatory activity in human PBMC assessed as inhibition of LPS-induced I... 28435528
Unchecked IC50 = 145.0 nM 6.84 Inhibition of human 20S proteasome beta 5i preincubated for 1 hr followed by flu... 31283222
Proteasome Macropain subunit MB1 IC50 = 150.0 nM 6.82 Inhibition of human 20S constitutive proteasome beta-5 using Suc-LLVY-AMC as sub... 29339252
Fibroblast EC50 = 160.0 nM 6.8 Cytotoxicity against human fibroblasts assessed as reduction in cell viability a... 29339252
Unchecked IC50 = 180.0 nM 6.75 Inhibition of 20s proteasome subunit beta-5c in human RPMI8226 cells using BODIP... 25006746
PBMC IC50 = 220.0 nM 6.66 Anti-inflammatory activity in human PBMC assessed as inhibition of LPS-induced G... 28435528
PBMC IC50 = 240.0 nM 6.62 Anti-inflammatory activity in human PBMC assessed as inhibition of LPS-induced I... 28435528
MM1.S IC50 = 240.0 nM 6.62 Antiproliferative activity against human MM1.S cells assessed as inhibition of c... 34087498

Literature References

PubMed DOI Target Context # Activities
25006746 10.1021/jm500716s Unchecked 14
31283222 10.1021/acs.jmedchem.9b00509 Unchecked 9
28435528 10.1021/acsmedchemlett.6b00496 PBMC 7
30380863 10.1021/acs.jmedchem.8b01201 PBMC 5
30380863 10.1021/acs.jmedchem.8b01201 Proteasome subunit beta type-10 3
30380863 10.1021/acs.jmedchem.8b01201 Proteasome subunit beta type-9 3
28435528 10.1021/acsmedchemlett.6b00496 Mus musculus 3
30380863 10.1021/acs.jmedchem.8b01201 Proteasome subunit beta type-8 3
28435528 10.1021/acsmedchemlett.6b00496 Liver 3
29339252 10.1016/j.ejmech.2018.01.013 Proteasome Macropain subunit 2
29339252 10.1016/j.ejmech.2018.01.013 Proteasome subunit beta type-9 2
29339252 10.1016/j.ejmech.2018.01.013 Proteasome subunit beta type-8 2
29339252 10.1016/j.ejmech.2018.01.013 Proteasome Macropain subunit MB1 2
29339252 10.1016/j.ejmech.2018.01.013 Proteasome component C5 2
29339252 10.1016/j.ejmech.2018.01.013 Proteasome subunit beta type-10 2
34087498 10.1016/j.ejmech.2021.113556 Proteasome subunit beta type-8 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
25006746 10.1021/jm500716s Proteasome subunit beta type-10 2
25006746 10.1021/jm500716s Proteasome subunit beta type-9 2
25006746 10.1021/jm500716s Proteasome subunit beta type-8 2

Data from ChEMBL 36 via Core Engine