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Compound Detail

CHEMBL1672002

THYMOQUINONE
🧪 Phase II
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🧪 Phase II
CC1=CC(=O)C(C(C)C)=CC1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1672002
Name THYMOQUINONE
Phase Phase II
Structure Type MOL
InChI Key KEQHJBNSCLWCAE-UHFFFAOYSA-N

Known Names

NSC-2228 P-cymene-2,5-dione P-mentha-3,6-diene-2,5-dione Thymoquinon Thymoquinone
17
Targets
26
Activities
2
Assay Types
2
PK Parameters
20
Publications
5
Known Names
2
Indications

Molecular Properties

164.2
MW (Da)
1.67
ALogP
2
HBA
0
HBD
34.1
PSA (Ų)
0.55
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C10H12O2
MW 164.20
Aromatic Rings 0
Heavy Atoms 12
NP-Likeness 1.55

Indications

Immunologic Deficiency Syndromes Severe Acute Respiratory Syndrome

Activity Summary

IC50 22 meas. best 5.92
EC50 4 meas. best 6.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ADR5000 cell line
CHEMBL614266
 EC50 6.52 6.52 300.0 2
CCRF-CEM
CHEMBL382
 EC50 6.52 6.52 300.0 2
Plasmodium falciparum
CHEMBL364
 IC50 5.92 5.48 1200.0 3
HeLa
CHEMBL399
 IC50 5.69 5.69 2060.0 1
Serine/threonine-protein kinase PLK1
CHEMBL3024
 IC50 5.66 5.66 2180.0 1
MCF7
CHEMBL387
 IC50 5.21 5.21 6190.0 1
Unchecked
CHEMBL612545
 IC50 5.11 4.93 7800.0 2
A2780
CHEMBL614004
 IC50 5.1 5.1 7900.0 1
Eukaryotic elongation factor 2 kinase
CHEMBL5026
 IC50 5.09 5.09 8200.0 1
OVCAR-8
CHEMBL612555
 IC50 4.94 4.94 11600.0 1
Serine/threonine-protein kinase PLK2
CHEMBL5938
 IC50 4.83 4.83 14720.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.57 4.54 27000.0 3
HL-60
CHEMBL383
 IC50 4.55 4.55 28000.0 1
HFF
CHEMBL614071
 IC50 4.48 4.48 33000.0 1
HT-29
CHEMBL384
 IC50 4.33 4.33 47000.0 1
PC-3
CHEMBL390
 IC50 4.3 4.3 50100.0 1
HCT-116
CHEMBL394
 IC50 4.3 4.3 50100.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 2436.05 nM Rattus norvegicus
Cmax 5481.12 nM Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ADR5000 cell line EC50 = 300.0 nM 6.52 Cytotoxicity against human CEM/ADR5000 cells over-expressing P-gp assessed as re... 29887512
ADR5000 cell line EC50 = 300.0 nM 6.52 Cytotoxicity against human CEM/ADR5000 cells overexpressing P-gp assessed as red... 29937978
CCRF-CEM EC50 = 300.0 nM 6.52 Cytotoxicity against human CCRF-CEM cells assessed as reduction in cell viabilit... 29937978
CCRF-CEM EC50 = 300.0 nM 6.52 Cytotoxicity against human CCRF-CEM cells assessed as reduction in cell viabilit... 29887512
Plasmodium falciparum IC50 = 1200.0 nM 5.92 Antiplasmodial activity against chloroquine and artemisinin sensitive Plasmodium... 29519737
Plasmodium falciparum IC50 = 1200.0 nM 5.92 Antiplasmodial activity against Plasmodium falciparum 33333397
HeLa IC50 = 2060.0 nM 5.69 Antiproliferative activity against human HeLa cells assessed as growth inhibitio... 25556101
Serine/threonine-protein kinase PLK1 IC50 = 2180.0 nM 5.66 Inhibition of recombinant Plk1 (unknown origin) preincubated for 30 mins before ... 25556101
MCF7 IC50 = 6190.0 nM 5.21 Antiproliferative activity against human MCF7 cells assessed as growth inhibitio... 25556101
Unchecked IC50 = 7800.0 nM 5.11 Growth inhibition of human A2780cis cells after 72 hrs by SRB assay 29519737
A2780 IC50 = 7900.0 nM 5.1 Growth inhibition of human A2780 cells after 72 hrs by SRB assay 29519737
Eukaryotic elongation factor 2 kinase IC50 = 8200.0 nM 5.09 Inhibition of eEF2K (unknown origin) by western blot analysis 33650861
OVCAR-8 IC50 = 11600.0 nM 4.94 Growth inhibition of human OVCAR8 cells after 72 hrs by SRB assay 29519737
Serine/threonine-protein kinase PLK2 IC50 = 14720.0 nM 4.83 Inhibition of recombinant Plk2 (unknown origin) 25556101
Unchecked IC50 = 17800.0 nM 4.75 Growth inhibition of SV-40 immortalized human ovarian epithelial cells after 72 ... 29519737
Plasmodium falciparum IC50 = 25000.0 nM 4.6 Antiplasmodial activity against Plasmodium falciparum Dd2 by SYBR Green I fluore... 29519737
NON-PROTEIN TARGET IC50 = 27000.0 nM 4.57 Cytotoxicity against human MCF7/Topo cells after 72 hrs by MTT assay 21216607
HL-60 IC50 = 28000.0 nM 4.55 Cytotoxicity against human HL60 cells after 72 hrs by MTT assay 21216607
NON-PROTEIN TARGET IC50 = 28000.0 nM 4.55 Cytotoxicity against human 518A2 cells after 72 hrs by MTT assay 21216607
NON-PROTEIN TARGET IC50 = 32000.0 nM 4.5 Cytotoxicity against human KB-V1/Vbl cells after 72 hrs by MTT assay 21216607

Literature References

PubMed DOI Target Context # Activities
18461966 10.1021/jf800331r Coptotermes formosanus 39
29456109 10.1016/j.bmcl.2018.02.016 HepG2 4
21216607 10.1016/j.bmc.2010.12.012 NON-PROTEIN TARGET 3
29031072 10.1016/j.ejmech.2017.09.068 Unchecked 3
- 10.1016/j.cropro.2011.09.009 Trichoplusia ni 3
29519737 10.1016/j.bmcl.2018.02.051 Unchecked 3
- 10.1039/C5MD00481K Rattus norvegicus 2
- 10.1101/2020.04.21.054387 SARS-CoV-2 2
29519737 10.1016/j.bmcl.2018.02.051 Plasmodium falciparum 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
24491635 10.1016/j.bmc.2014.01.009 NON-PROTEIN TARGET 1
25556101 10.1016/j.bmcl.2014.12.060 Unchecked 1
25556101 10.1016/j.bmcl.2014.12.060 MCF7 1
25556101 10.1016/j.bmcl.2014.12.060 HeLa 1
25556101 10.1016/j.bmcl.2014.12.060 Serine/threonine-protein kinase PLK1 1
24984937 10.1016/j.bmc.2014.06.004 Botulinum neurotoxin type A 1
31945642 10.1016/j.ejmech.2020.112044 PC-3 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23062825 10.1016/j.bmc.2012.09.040 Cholinesterase 1
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1

Data from ChEMBL 36 via Core Engine