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Compound Detail

CHEMBL43612

JUGLONE
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O=C1C=CC(=O)c2c(O)cccc21

Basic Information

ChEMBL ID CHEMBL43612
Name JUGLONE
Phase Preclinical
Structure Type MOL
InChI Key KQPYUDDGWXQXHS-UHFFFAOYSA-N
40
Targets
65
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

174.2
MW (Da)
1.33
ALogP
3
HBA
1
HBD
54.4
PSA (Ų)
0.65
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C10H6O3
MW 174.16
Aromatic Rings 1
Heavy Atoms 13
NP-Likeness 1.49

Activity Summary

IC50 64 meas. best 8.92
EC50 1 meas. best 5.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mycobacterium tuberculosis
CHEMBL360
IC50 8.92 8.92 1.2 1
Unchecked
CHEMBL612545
IC50 7.8 5.8 15.8 3
Aurora kinase A
CHEMBL4722
IC50 7.3 7.3 50.0 1
Aurora kinase B
CHEMBL2185
IC50 6.21 6.21 620.0 1
Protein disulfide-isomerase
CHEMBL5422
IC50 6.2 6.08 630.0 2
HaCaT
CHEMBL614392
IC50 6.1 6.1 800.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
IC50 6.0 6.0 1000.0 1
Platelet
CHEMBL4296519
IC50 5.93 5.64 1180.0 2
A2780
CHEMBL614004
IC50 5.85 5.85 1400.0 1
Transient receptor potential cation channel subfamily A member 1
CHEMBL6007
EC50 5.77 5.77 1700.0 1
M-phase inducer phosphatase 2
CHEMBL4804
IC50 5.7 5.7 1980.0 1
Protein disulfide-isomerase A3
CHEMBL4296001
IC50 5.62 5.62 2400.0 1
Protein disulfide-isomerase A4
CHEMBL4295717
IC50 5.5 5.5 3160.0 1
RPMI-8226
CHEMBL614882
IC50 5.4 5.4 3950.0 1
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1
CHEMBL2288
IC50 5.3 5.0783 5000.0 6
EA.hy 926
CHEMBL4296410
IC50 5.25 5.25 5570.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.22 4.8325 6000.0 4
MDA-MB-231
CHEMBL400
IC50 5.21 4.65 6150.0 4
Trypanosoma cruzi
CHEMBL368
IC50 5.19 5.19 6510.0 1
KB
CHEMBL398
IC50 5.18 5.18 6550.0 1
SK-MEL-28
CHEMBL614919
IC50 5.16 5.16 7000.0 1
A549
CHEMBL392
IC50 5.16 5.045 7000.0 2
U-87 MG
CHEMBL614247
IC50 5.13 5.13 7450.0 1
HT-29
CHEMBL384
IC50 5.11 5.11 7710.0 1
DNA topoisomerase 1
CHEMBL1781
IC50 5.08 5.08 8260.0 1
DU-145
CHEMBL613508
IC50 4.93 4.93 11670.0 1
Dual specificity protein phosphatase 6
CHEMBL5511
IC50 4.91 4.91 12400.0 1
Dual specificity protein phosphatase 1
CHEMBL5623
IC50 4.89 4.89 13000.0 1
MCF7
CHEMBL387
IC50 4.89 4.8167 13000.0 3
J774.2
CHEMBL614484
IC50 4.87 4.87 13360.0 1
LNCaP
CHEMBL612518
IC50 4.86 4.86 13800.0 1
HeLa
CHEMBL399
IC50 4.8 4.242 15730.0 5
Arachidonate 5-lipoxygenase
CHEMBL2980
IC50 4.77 4.77 17000.0 1
HepG2
CHEMBL395
IC50 4.69 4.69 20430.0 1
KB 3-1
CHEMBL614590
IC50 4.58 4.58 26400.0 1
MDA-MB-453
CHEMBL614334
IC50 4.56 4.56 27500.0 2
HCT-116
CHEMBL394
IC50 4.5 4.5 31600.0 1
ADMET
CHEMBL612558
IC50 4.46 4.46 34270.0 1
ME-180
CHEMBL1075499
IC50 4.18 4.18 65400.0 1
PC-3
CHEMBL390
IC50 4.05 4.05 88700.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mycobacterium tuberculosis IC50 = 1.2 nM 8.92 Antitubercular activity against Mycobacterium tuberculosis H37Rv by BACTEC metho... -
Unchecked IC50 = 15.75 nM 7.8 Inhibition of SARS-CoV-2 main protease by tandem mass spectrometry analysis 34438124
Aurora kinase A IC50 = 50.0 nM 7.3 Inhibition of Aurora A (unknown origin) 35687347
Aurora kinase B IC50 = 620.0 nM 6.21 Inhibition of Aurora B (unknown origin) 35687347
Protein disulfide-isomerase IC50 = 630.0 nM 6.2 Inhibition of PDI in human platelets assessed as inhibition of E-GSH formation u... 38381886
HaCaT IC50 = 800.0 nM 6.1 Antiproliferative (inhibition of cell growth) activity against HaCaT cells (huma... 9371243
Indoleamine 2,3-dioxygenase 1 IC50 = 1000.0 nM 6.0 Inhibition of purified human recombinant IDO 18318466
Protein disulfide-isomerase IC50 = 1100.0 nM 5.96 Inhibition of human recombinant PDI assessed as inhibition of E-GSH formation us... 38381886
Platelet IC50 = 1180.0 nM 5.93 Antiplatelet activity in human platelets assessed as inhibition of collagen-indu... 38381886
A2780 IC50 = 1400.0 nM 5.85 Antiproliferative activity against human A2780 cells after 2 days by alamar-blue... 19028102
Transient receptor potential cation channel subfamily A member 1 EC50 = 1700.0 nM 5.77 Activation of human TRPA1 expressed in HEK293 cells assessed as increase in calc... 26905390
M-phase inducer phosphatase 2 IC50 = 1980.0 nM 5.7 Inhibition of histidine-tagged human recombinant Cdc25B catalytic domain express... 19028102
Protein disulfide-isomerase A3 IC50 = 2400.0 nM 5.62 Inhibition of human recombinant ERp57 assessed as inhibition of E-GSH formation ... 38381886
Protein disulfide-isomerase A4 IC50 = 3160.0 nM 5.5 Inhibition of human recombinant ERp72 assessed as inhibition of E-GSH formation ... 38381886
Unchecked IC50 = 3700.0 nM 5.43 In vitro antimalarial activity against human malaria parasite, P falciparum (Vie... 2033589
RPMI-8226 IC50 = 3950.0 nM 5.4 Cytotoxicity against human RPMI-8226 cells assessed as reduction in cell viabili... 38381886
Platelet IC50 = 4450.0 nM 5.35 Antiplatelet activity in human platelets assessed as inhibition of U46619-induce... 38381886
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 IC50 = 5000.0 nM 5.3 Inhibition of human Pin1 using Suc-AEPF-NH-Np as substrate 37438908
EA.hy 926 IC50 = 5570.0 nM 5.25 Cytotoxicity against human EA.hy 926 cells assessed as reduction in cell viabili... 38381886
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 IC50 = 5900.0 nM 5.23 Inhibition of human N-terminal His6-tagged Pin1 PPIase activity expressed in Esc... 29576270

Literature References

PubMed DOI Target Context # Activities
23163769 10.1021/jf303584r Erwinia amylovora 28
23643730 10.1016/j.bmcl.2013.04.007 LNCaP 15
26905390 10.1021/acs.jnatprod.5b00396 Transient receptor potential cation channel subfamily A member 1 7
- 10.1016/j.cropro.2011.09.009 Trichoplusia ni 5
21903399 10.1016/j.bmc.2011.08.023 Unchecked 4
26706169 10.1016/j.bmcl.2015.12.017 NON-PROTEIN TARGET 4
2558164 10.1021/np50065a012 Unchecked 4
2558164 10.1021/np50065a012 Raji 4
17284452 10.1074/jbc.m608207200 Unchecked 4
24631733 10.1016/j.ejmech.2014.03.006 HeLa 4
34438124 10.1016/j.ejmech.2021.113789 Unchecked 3
38381886 10.1021/acs.jmedchem.3c02107 Unchecked 3
21903399 10.1016/j.bmc.2011.08.023 RAW264.7 3
24984937 10.1016/j.bmc.2014.06.004 Botulinum neurotoxin type A 3
38381886 10.1021/acs.jmedchem.3c02107 Protein disulfide-isomerase 3
24913712 10.1016/j.bmcl.2014.04.080 Staphylococcus aureus 2
21903399 10.1016/j.bmc.2011.08.023 DNA polymerase kappa 2
- 10.1007/s00044-011-9731-0 Mycobacterium tuberculosis 2
38522112 10.1016/j.ejmech.2024.116338 ADMET 2
9371243 10.1021/jm970292n HaCaT 2

Data from ChEMBL 36 via Core Engine