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Compound Detail

CHEMBL2326533

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CC(C)C[C@H](NC(=O)[C@H](Cc1ccccc1)N=[N+]=[N-])C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](/C=C/S(C)(=O)=O)Cc1ccc(CN)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2326533
Phase Preclinical
Structure Type MOL
InChI Key CYXJGNUHXUIEQM-MOAULALOSA-N
6
Targets
25
Activities
1
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

653.9
MW (Da)
3.71
ALogP
7
HBA
4
HBD
196.2
PSA (Ų)
0.11
QED
1
Ro5 Violations
18
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C33H47N7O5S
MW 653.85
Aromatic Rings 2
Heavy Atoms 46
NP-Likeness 0.17

Activity Summary

IC50 25 meas. best 8.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.42 6.028 3.8 5
Proteasome Macropain subunit
CHEMBL3492
 IC50 7.97 7.0171 10.8 7
Proteasome subunit beta type-10
CHEMBL3317334
 IC50 7.7 7.2167 20.0 3
Proteasome subunit beta type-8
CHEMBL5620
 IC50 5.93 5.84 1170.0 2
Proteasome Macropain subunit MB1
CHEMBL4662
 IC50 5.92 5.4483 1200.0 6
Proteasome component C5
CHEMBL4208
 IC50 5.8 5.73 1600.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 3.8 nM 8.42 Inhibition of trypsin-like activity of rabbit 26s proteasome beta 2 subunit asse... 23320547
Proteasome Macropain subunit IC50 = 10.8 nM 7.97 Inhibition of human 20S constitutive proteasome beta-2 using Bz-VGR-AMC as subst... 29782167
Proteasome Macropain subunit IC50 = 13.0 nM 7.89 Inhibition of 20S constitutive proteasome beta 2 trypsin-like activity in human ... 30657666
Proteasome subunit beta type-10 IC50 = 20.0 nM 7.7 Inhibition of 20S immunoproteasome beta 2 in human Raji cell lysates after 1 hr ... 30657666
Proteasome subunit beta type-10 IC50 = 27.5 nM 7.56 Inhibition of human 20S immunoproteasome beta-2 using Bz-VGR-AMC as substrate af... 29782167
Proteasome Macropain subunit IC50 = 50.0 nM 7.3 Inhibition of trypsin-like activity of proteasome in human NCI-H929 cells after ... 23320547
Proteasome Macropain subunit IC50 = 84.0 nM 7.08 Inhibition of trypsin-like activity of proteasome beta 2 subunit in HEK-293T cel... 23320547
Proteasome Macropain subunit IC50 = 170.0 nM 6.77 Inhibition of trypsin-like activity of proteasome in human RPMI-8226 cells after... 23320547
Proteasome Macropain subunit IC50 = 290.0 nM 6.54 Inhibition of 20S constitutive proteasome beta 2 trypsin-like activity in human ... 30657666
Proteasome subunit beta type-10 IC50 = 410.0 nM 6.39 Inhibition of 20S immunoproteasome beta 2 in human RPMI8226 cell lysates after 1... 30657666
Proteasome subunit beta type-8 IC50 = 1170.0 nM 5.93 Inhibition of 20S immunoproteasome beta 5 in human Raji cell lysates after 1 hr ... 30657666
Proteasome Macropain subunit MB1 IC50 = 1200.0 nM 5.92 Inhibition of chymotrypsin-like activity of proteasome in human RPMI-8226 cells ... 23320547
Proteasome Macropain subunit MB1 IC50 = 1330.0 nM 5.88 Inhibition of 20S constitutive proteasome beta 5 chymotrypsin-like activity in h... 30657666
Proteasome component C5 IC50 = 1600.0 nM 5.8 Inhibition of caspase-like activity of proteasome in human RPMI-8226 cells after... 23320547
Proteasome Macropain subunit MB1 IC50 = 1700.0 nM 5.77 Inhibition of chymotrypsin-like activity of proteasome in human NCI-H929 cells a... 23320547
Unchecked IC50 = 1700.0 nM 5.77 Inhibition of chymotrypsin-like activity of rabbit 26s proteasome beta 5 subunit... 23320547
Proteasome subunit beta type-8 IC50 = 1800.0 nM 5.75 Inhibition of human 20S immunoproteasome beta-5 using Suc-LLVY-AMC as substrate ... 29782167
Proteasome component C5 IC50 = 2200.0 nM 5.66 Inhibition of caspase-like activity of proteasome in human NCI-H929 cells at 200... 23320547
Unchecked IC50 = 2600.0 nM 5.58 Inhibition of trypsin-like activity of yeast 20s proteasome beta 2 subunit asses... 23320547
Proteasome Macropain subunit MB1 IC50 = 2600.0 nM 5.58 Inhibition of human 20S constitutive proteasome beta-5 using Suc-LLVY-AMC as sub... 29782167

Literature References

PubMed DOI Target Context # Activities
23320547 10.1021/jm3016987 Unchecked 10
23320547 10.1021/jm3016987 Proteasome Macropain subunit 6
30657666 10.1021/acs.jmedchem.8b01884 Unchecked 6
23320547 10.1021/jm3016987 RPMI-8226 4
30657666 10.1021/acs.jmedchem.8b01884 Proteasome subunit beta type-10 4
23320547 10.1021/jm3016987 Proteasome Macropain subunit MB1 4
30657666 10.1021/acs.jmedchem.8b01884 Proteasome Macropain subunit 3
23320547 10.1021/jm3016987 Proteasome component C5 3
29782167 10.1021/acs.jmedchem.8b00685 Unchecked 2
30657666 10.1021/acs.jmedchem.8b01884 Proteasome Macropain subunit MB1 2
30657666 10.1021/acs.jmedchem.8b01884 Proteasome subunit beta type-8 2
30657666 10.1021/acs.jmedchem.8b01884 Proteasome component C5 2
30657666 10.1021/acs.jmedchem.8b01884 Proteasome subunit beta type-9 2
29782167 10.1021/acs.jmedchem.8b00685 Proteasome Macropain subunit 1
29782167 10.1021/acs.jmedchem.8b00685 Proteasome Macropain subunit MB1 1
29782167 10.1021/acs.jmedchem.8b00685 Proteasome subunit beta type-10 1
29782167 10.1021/acs.jmedchem.8b00685 Proteasome subunit beta type-8 1

Data from ChEMBL 36 via Core Engine