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Compound Detail

CHEMBL207990

EPOXOMYCIN
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CC[C@H](C)[C@H](NC(=O)[C@H]([C@@H](C)CC)N(C)C(C)=O)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)[C@@]1(C)CO1)[C@@H](C)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL207990
Name EPOXOMYCIN
Phase Preclinical
Structure Type BOTH
InChI Key DOGIDQKFVLKMLQ-JTHVHQAWSA-N
14
Targets
52
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

554.7
MW (Da)
1.16
ALogP
7
HBA
4
HBD
157.4
PSA (Ų)
0.21
QED
1
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Protein
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H50N4O7
MW 554.73
Aromatic Rings 0
Heavy Atoms 39
NP-Likeness 0.74

Activity Summary

IC50 51 meas. best 9.52
EC50 1 meas. best 6.65

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 9.52 8.3525 0.3 12
PC-3
CHEMBL390
 IC50 9.0 9.0 1.0 1
Plasmodium falciparum K1
CHEMBL612856
 IC50 8.55 8.55 2.8 1
Proteasome Macropain subunit MB1
CHEMBL4662
 IC50 8.43 7.78 3.7 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.4 8.36 4.0 2
Unchecked
CHEMBL612545
 IC50 8.3 6.811 5.0 21
RPMI-8226
CHEMBL614882
 IC50 7.96 7.96 11.0 1
HEK293
CHEMBL614818
 IC50 7.47 7.47 33.6 1
Proteasome Macropain subunit
CHEMBL3492
 IC50 6.8 6.405 160.0 2
Schistosoma mansoni
CHEMBL612893
 EC50 6.65 6.65 226.0 1
Proteasome
CHEMBL612443
 IC50 6.58 6.58 261.0 1
Proteasome component C5
CHEMBL4208
 IC50 6.52 6.09 300.0 2
Plasmodium yoelii yoelii
CHEMBL612328
 IC50 5.4 5.4 3950.0 2
Cathepsin S
CHEMBL2954
 IC50 4.6 4.6 25000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.3 nM 9.52 OSM: Late stage gametocytes. IC50 values determined from 21 point dose response ... -
Plasmodium falciparum IC50 = 0.7 nM 9.15 Antimalarial activity against late (4 to 5) gametocytic stage of Plasmodium falc... 23927763
Plasmodium falciparum IC50 = 0.7 nM 9.15 Gametocytocidal activity against Plasmodium falciparum NF54 HGL gametocytes asse... 29571157
PC-3 IC50 = 1.0 nM 9.0 Antiproliferative activity against human PC3 cell line 16686537
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antimalarial activity against Plasmodium falciparum stage 3 to 5 gametocytes 23075290
Plasmodium falciparum IC50 = 2.2 nM 8.66 Antimalarial activity against asexual stage of Plasmodium falciparum 3D7 after 7... 23927763
Plasmodium falciparum K1 IC50 = 2.8 nM 8.55 OSM: Inhibition of Plasmodium falciparum K1 growth. IC50 values determined from ... -
Proteasome Macropain subunit MB1 IC50 = 3.7 nM 8.43 Inhibition of chymotrypsin-like proteasome activity of human 20S proteasome 16686537
NON-PROTEIN TARGET IC50 = 4.0 nM 8.4 Antiproliferative activity of the compound 10612595
Plasmodium falciparum IC50 = 4.2 nM 8.38 OSM: Inhibition of Plasmodium falciparum 3D7 growth. IC50 values determined from... -
NON-PROTEIN TARGET IC50 = 4.8 nM 8.32 Cytotoxicity against human WM266.4 cells after 72 hrs by ATPlite assay 22206869
Unchecked IC50 = 5.0 nM 8.3 Inhibition of chymotrypsin-like activity of 20S proteasome 18294845
Unchecked IC50 = 5.0 nM 8.3 Inhibition of chymotrypsin-like activity of 20S proteasome beta2 in human LCL ce... 20687609
Unchecked IC50 = 5.0 nM 8.3 Inhibition of chymotrypsin trypsin-like activity of proteasome from human LCL af... 19577931
Unchecked IC50 = 5.0 nM 8.3 Inhibition of chymotrypsin like 20S proteasome activity in lymphoblastoid cells 17996987
Unchecked IC50 = 6.0 nM 8.22 Inhibition of chymotrypsin-like activity of 20S proteasome in human DLD1 cells t... 22206869
Plasmodium falciparum IC50 = 7.0 nM 8.15 Gametocytocidal activity against Plasmodium falciparum 3D7 elo1-pfs16-CBG99 late... 29571157
Plasmodium falciparum IC50 = 7.0 nM 8.15 Gametocytocidal activity against synchronized Plasmodium falciparum NF54 mature ... 30245402
Unchecked IC50 = 9.0 nM 8.05 Inhibition of chymotrypsin-like activity of 20S proteasome beta 5 subunit by flu... 19250821
Unchecked IC50 = 9.0 nM 8.05 Inhibition of chymotrypsin trypsin-like activity of proteasome from human PBMC a... 19577931

Literature References

PubMed DOI Target Context # Activities
19577931 10.1016/j.bmc.2009.06.025 Unchecked 6
19651911 10.1128/aac.00088-09 Plasmodium falciparum 6
- 10.6019/CHEMBL5096127 Schistosoma mansoni 4
22206869 10.1016/j.bmc.2011.11.066 Unchecked 4
19250821 10.1016/j.bmcl.2009.02.046 Unchecked 3
23927763 10.1021/jm4004279 Plasmodium falciparum 3
17996987 10.1016/j.ejmech.2007.10.002 Unchecked 3
10612595 10.1016/s0960-894x(99)00612-5 Unchecked 3
18294845 10.1016/j.bmcl.2008.02.016 Unchecked 3
20687609 10.1021/jm100122e Unchecked 3
38428537 10.1016/j.bmcl.2024.129680 Unchecked 2
30964987 10.1021/acs.jmedchem.8b01943 Unchecked 2
16686537 10.1021/jm058289o Proteasome Macropain subunit MB1 2
- 10.6019/CHEMBL2113921 Plasmodium falciparum 2
29571157 10.1016/j.ejmech.2018.03.024 Plasmodium falciparum 2
16686537 10.1021/jm058289o Proteasome component C5 1
16686537 10.1021/jm058289o PC-3 1
16686537 10.1021/jm058289o Cathepsin S 1
16686537 10.1021/jm058289o Cathepsin B 1
10465562 10.1016/s0960-894x(99)00376-5 Cathepsin S 1

Data from ChEMBL 36 via Core Engine