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Compound Detail

CHEMBL221137

EMBELIN
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CCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O

Basic Information

ChEMBL ID CHEMBL221137
Name EMBELIN
Phase Preclinical
Structure Type MOL
InChI Key IRSFLDGTOHBADP-UHFFFAOYSA-N
585
Targets
712
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

294.4
MW (Da)
4.31
ALogP
4
HBA
2
HBD
74.6
PSA (Ų)
0.46
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C17H26O4
MW 294.39
Aromatic Rings 0
Heavy Atoms 21
NP-Likeness 1.58

Activity Summary

IC50 694 meas. best 7.22
EC50 15 meas. best 7.05
Ki 3 meas. best 7.63

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
G-protein coupled receptor 84
CHEMBL3714079
Ki 7.63 7.63 23.6 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
IC50 7.22 6.265 60.0 6
G-protein coupled receptor 84
CHEMBL3714079
EC50 7.05 6.2427 89.0 11
Unchecked
CHEMBL612545
Ki 6.72 6.72 190.0 1
Prostaglandin E synthase
CHEMBL5658
IC50 6.7 6.7 200.0 1
Macrophage-expressed gene 1 protein
CHEMBL3414409
IC50 6.68 6.68 210.0 2
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
Ki 6.4 6.4 400.0 1
SIG-M5
CHEMBL2366251
IC50 5.88 5.88 1310.6 1
A549
CHEMBL392
IC50 5.83 5.83 1470.0 1
HCT-8
CHEMBL613510
IC50 5.83 5.83 1490.0 1
Streptococcus sp. 'group A'
CHEMBL612389
EC50 5.8 5.8 1576.0 1
NTERA-2-cl-D1
CHEMBL614206
IC50 5.8 5.8 1596.2 1
Streptokinase A
CHEMBL1293228
EC50 5.78 5.78 1671.0 1
Bel-7402
CHEMBL614279
IC50 5.78 5.78 1660.0 1
BGC-823
CHEMBL614526
IC50 5.77 5.77 1690.0 1
UACC-62
CHEMBL614610
IC50 5.76 5.76 1747.7 1
SF-295
CHEMBL614908
IC50 5.76 5.76 1754.8 1
A2780
CHEMBL614004
IC50 5.75 5.315 1790.0 2
RKO
CHEMBL614879
IC50 5.7 5.7 2006.8 1
Unchecked
CHEMBL612545
IC50 5.68 5.5367 2100.0 3
IA-LM
CHEMBL2366366
IC50 5.65 5.65 2226.5 1
A2058
CHEMBL613503
IC50 5.63 5.63 2321.8 1
HuTu80
CHEMBL614582
IC50 5.63 5.63 2354.4 1
PA-1
CHEMBL614949
IC50 5.63 5.63 2321.8 1
C32
CHEMBL1075401
IC50 5.55 5.55 2825.8 1
NCI-H2122
CHEMBL1075533
IC50 5.55 5.55 2810.1 1
MC116
CHEMBL2366256
IC50 5.55 5.55 2818.2 1
CCRF-CEM
CHEMBL382
IC50 5.52 5.52 3016.2 1
CHP-212
CHEMBL1075423
IC50 5.51 5.51 3121.5 1
No relevant target
CHEMBL2362975
IC50 5.51 5.51 3120.0 2
D-542MG
CHEMBL2366208
IC50 5.5 5.5 3126.3 1
KGN
CHEMBL2366154
IC50 5.49 5.49 3217.7 1
Streptococcus
CHEMBL612313
EC50 5.48 5.48 3319.0 1
KE-37
CHEMBL2366287
IC50 5.46 5.46 3443.9 1
8-MG-BA
CHEMBL2366115
IC50 5.45 5.45 3532.1 1
A-375
CHEMBL613859
IC50 5.45 5.45 3572.5 1
S-117
CHEMBL1075568
IC50 5.44 5.44 3629.6 1
GT3TKB
CHEMBL2366148
IC50 5.44 5.44 3619.9 1
ALL-PO
CHEMBL2366294
IC50 5.44 5.44 3646.6 1
PC-3
CHEMBL390
IC50 5.43 5.23 3700.0 3
GI-1
CHEMBL2366272
IC50 5.42 5.42 3763.5 1
NH-12
CHEMBL2366263
IC50 5.41 5.41 3881.5 1
COLO 205
CHEMBL614561
IC50 5.41 5.41 3867.4 1
LoVo
CHEMBL614721
IC50 5.41 5.41 3868.9 1
SAOS-2
CHEMBL614894
IC50 5.4 5.4 3945.3 1
E3 ubiquitin-protein ligase XIAP
CHEMBL4198
IC50 5.39 5.39 4100.0 3
RPMI 8402
CHEMBL612517
IC50 5.39 5.39 4054.4 1
DMS-273
CHEMBL614034
IC50 5.39 5.39 4059.4 1
COLO-679
CHEMBL1075426
IC50 5.38 5.38 4197.9 1
H4
CHEMBL1075452
IC50 5.38 5.38 4131.4 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
G-protein coupled receptor 84 Ki = 23.6 nM 7.63 Displacement of [3H]PSB-1584 from recombinant human GPR84 expressed in CHO cell ... 31721581
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 60.0 nM 7.22 Inhibition of human 5-LOX by cell free assay 25765759
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 60.0 nM 7.22 Inhibition of human recombinant 5-LOX expressed in Escherichia coli BL21 incubat... 25765759
G-protein coupled receptor 84 EC50 = 89.0 nM 7.05 Agonist activity at hemagglutinin-tagged human GPR84 expressed in HEK293 cells a... 38146625
G-protein coupled receptor 84 EC50 = 89.0 nM 7.05 Agonist activity at recombinant human HA-tagged GPR84 stably expressed in HEK293... 31721581
Unchecked Ki = 190.0 nM 6.72 Binding affinity to NDM-1 (unknown origin) assessed as inhibition constant using... 34225181
G-protein coupled receptor 84 EC50 = 200.0 nM 6.7 Agonist activity at recombinant human N-terminal epitope tagged/C-terminal eYFP-... 31721581
Prostaglandin E synthase IC50 = 200.0 nM 6.7 Inhibition of mPGES1 in human A549 cell microsomes 29329790
Macrophage-expressed gene 1 protein IC50 = 210.0 nM 6.68 Inhibition of mPGES1 in IL-1beta stimulated human A549 cell microsomal membranes... 25765759
Macrophage-expressed gene 1 protein IC50 = 210.0 nM 6.68 Inhibition of human mPGES1 25765759
E3 ubiquitin-protein ligase XIAP Ki = 400.0 nM 6.4 Binding affinity to recombinant XIAP BIR3 by FP assay 16962773
G-protein coupled receptor 84 EC50 = 400.0 nM 6.4 Agonist activity at human GPR84 expressed in CHO cells assessed as beta-arrestin... 28406627
G-protein coupled receptor 84 EC50 = 421.0 nM 6.38 Agonist activity at recombinant human GPR84 expressed in CHO cells assessed as i... 31721581
G-protein coupled receptor 84 EC50 = 421.0 nM 6.38 Agonist activity at human PK-tagged GPR84 expressed in CHOK1 cells assessed as E... 28406627
G-protein coupled receptor 84 EC50 = 630.0 nM 6.2 Agonist activity at recombinant human N-terminal epitope tagged/C-terminal eYFP-... 31721581
G-protein coupled receptor 84 EC50 = 630.0 nM 6.2 Agonist activity at recombinant human GPR84 expressed in HEK293 cells co-express... 31721581
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 800.0 nM 6.1 Inhibition of human 5-LOX by intact cell based assay 25765759
G-protein coupled receptor 84 EC50 = 795.0 nM 6.1 Agonist activity at Gi coupled human GPR84 expressed in CHO cells assessed as in... 28406627
SIG-M5 IC50 = 1310.62 nM 5.88 SANGER: Inhibition of human SIG-M5 cell growth in a cell viability assay. -
HCT-8 IC50 = 1490.0 nM 5.83 Cytotoxicity against human HCT8 cells after 96 hrs by MTT assay 17125236

Literature References

PubMed DOI Target Context # Activities
15115387 10.1021/jm030420+ PC-3 10
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 9
31721581 10.1021/acs.jmedchem.9b01339 G-protein coupled receptor 84 9
38389875 10.1039/d3md00564j ADMET 9
38389875 10.1039/d3md00564j No relevant target 7
25765759 10.1016/j.ejmech.2015.02.042 Polyunsaturated fatty acid 5-lipoxygenase 6
- 10.1007/s00044-013-0485-8 Mycobacterium tuberculosis 5
28406627 10.1021/acs.jmedchem.6b01593 G-protein coupled receptor 84 5
18461966 10.1021/jf800331r Coptotermes formosanus 4
15115387 10.1021/jm030420+ Jurkat 3
- 10.1007/s00044-011-9867-y NON-PROTEIN TARGET 3
34225181 10.1016/j.ejmech.2021.113667 Unchecked 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
36749898 10.1021/acs.jnatprod.2c00924 H9c2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
26924672 10.1021/acs.jnatprod.5b01038 Staphylococcus aureus 2
36749898 10.1021/acs.jnatprod.2c00924 J774.A1 2
15115387 10.1021/jm030420+ PrEC 2
15115387 10.1021/jm030420+ LNCaP 2
15115387 10.1021/jm030420+ E3 ubiquitin-protein ligase XIAP 2

Data from ChEMBL 36 via Core Engine