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Compound Detail

CHEMBL403516

ACETYLSHIKONIN
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CC(=O)O[C@H](CC=C(C)C)C1=CC(=O)c2c(O)ccc(O)c2C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL403516
Name ACETYLSHIKONIN
Phase Preclinical
Structure Type MOL
InChI Key WNFXUXZJJKTDOZ-OAHLLOKOSA-N
19
Targets
34
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

330.3
MW (Da)
2.69
ALogP
6
HBA
2
HBD
100.9
PSA (Ų)
0.50
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H18O6
MW 330.34
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 2.31

Activity Summary

IC50 33 meas. best 7.17
Ki 1 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bel-7402
CHEMBL614279
 IC50 7.17 7.17 68.0 1
SGC-7901
CHEMBL614909
 IC50 6.54 6.54 290.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 6.46 5.4967 350.0 3
HepG2
CHEMBL395
 IC50 6.42 5.805 380.0 2
COP9 signalosome complex subunit 5
CHEMBL4105809
 IC50 6.37 6.17 430.0 2
HCT-116
CHEMBL394
 IC50 6.35 5.6167 450.0 3
CCRF-CEM
CHEMBL382
 IC50 6.0 6.0 1000.0 1
Unchecked
CHEMBL612545
 Ki 6.0 6.0 1010.0 1
A-375
CHEMBL613859
 IC50 5.72 5.72 1910.0 1
Unchecked
CHEMBL612545
 IC50 5.7 5.6533 2000.0 3
MRC5
CHEMBL614181
 IC50 5.58 5.58 2600.0 1
MDA-MB-231
CHEMBL400
 IC50 4.95 4.95 11300.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.89 4.545 13000.0 4
U-251
CHEMBL615022
 IC50 4.8 4.8 15900.0 1
K562
CHEMBL385
 IC50 4.54 4.54 29000.0 1
MCF7
CHEMBL387
 IC50 4.51 4.51 31000.0 1
Telomerase reverse transcriptase
CHEMBL2916
 IC50 4.43 4.43 37300.0 1
A549
CHEMBL392
 IC50 4.41 4.41 39000.0 1
Neuraminidase
CHEMBL1795169
 IC50 4.38 4.38 41400.0 1
DNA topoisomerase 1
CHEMBL1781
 IC50 4.35 4.35 45000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bel-7402 IC50 = 68.0 nM 7.17 Tested in vitro for inhibitory effect on the growth of BEL -7402 cell line 11992780
SGC-7901 IC50 = 290.0 nM 6.54 Tested in vitro for inhibitory effect on the growth of human gastric carcinoma S... 11992780
Replicase polyprotein 1ab IC50 = 350.0 nM 6.46 Inhibition of SARS-CoV-2 Main protease 38508325
HepG2 IC50 = 380.0 nM 6.42 Cytotoxicity against MDR1 Pgp overexpressing human HepG2 cells after 24 hrs by M... 17949858
COP9 signalosome complex subunit 5 IC50 = 430.0 nM 6.37 Inhibition of N-terminal His6-tagged CSN5 (2 to 257 residues) (unknown origin) t... 39129245
HCT-116 IC50 = 450.0 nM 6.35 Cytotoxicity against MDR1 Pgp under-expressing human HCT116 cells after 24 hrs b... 17949858
Unchecked Ki = 1010.0 nM 6.0 Reversible inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-ter... 22300884
CCRF-CEM IC50 = 1000.0 nM 6.0 Cytotoxicity against human CCRF-CEM cells after 72 hrs by XTT assay 22530779
COP9 signalosome complex subunit 5 IC50 = 1070.0 nM 5.97 Inhibition of N-terminal His6-tagged CSN5 (2 to 257 residues) (unknown origin) t... 39129245
A-375 IC50 = 1910.0 nM 5.72 Antiproliferative activity against human A-375 cells assessed as inhibition of c... 39129245
Unchecked IC50 = 2000.0 nM 5.7 Inhibition of histamine release from rat mast cells 17320246
Unchecked IC50 = 2200.0 nM 5.66 Inhibition of beta-glucuronidase release from rat mast cells 17320246
Unchecked IC50 = 2500.0 nM 5.6 Inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-terminal catal... 22300884
MRC5 IC50 = 2600.0 nM 5.58 Cytotoxicity against human MRC5 cells after 72 hrs by XTT assay 22530779
HCT-116 IC50 = 3560.0 nM 5.45 Antiproliferative activity against human HCT-116 cells assessed as inhibition of... 39129245
Replicase polyprotein 1ab IC50 = 3800.0 nM 5.42 Inhibition of SARS-CoV-2 MPro 36651644
HepG2 IC50 = 6480.0 nM 5.19 Antiproliferative activity against human HepG2 cells assessed as inhibition of c... 39129245
HCT-116 IC50 = 9000.0 nM 5.05 Cytotoxicity against human HCT116 cells after 72 hrs by XTT assay 22530779
MDA-MB-231 IC50 = 11300.0 nM 4.95 Cytotoxicity against human MDA-MB-231 cells after 72 hrs by XTT assay 22530779
NON-PROTEIN TARGET IC50 = 13000.0 nM 4.89 Cytotoxicity against human SBcl2 cells after 72 hrs by XTT assay 22530779

Literature References

PubMed DOI Target Context # Activities
22300884 10.1016/j.bmc.2012.01.011 Unchecked 8
12502328 10.1021/np010599w Enterococcus faecalis 6
12502328 10.1021/np010599w Staphylococcus aureus 6
- 10.1584/jpestics.23.54 Cladosporium herbarum 4
36651644 10.1021/acs.jnatprod.2c00843 Replicase polyprotein 1ab 4
22530779 10.1021/np2006499 NON-PROTEIN TARGET 4
11992780 10.1016/s0960-894x(02)00158-0 DNA polymerase I, thermostable 3
22300884 10.1016/j.bmc.2012.01.011 Neuraminidase 3
12502328 10.1021/np010599w Enterococcus faecium 3
17320246 10.1016/j.ejmech.2006.12.009 Unchecked 2
22530779 10.1021/np2006499 MRC5 2
- 10.1584/jpestics.23.54 Tobacco mosaic virus 2
38508325 10.1016/j.bmcl.2024.129706 Replicase polyprotein 1ab 2
39129245 10.1021/acs.jmedchem.4c01514 COP9 signalosome complex subunit 5 2
11992780 10.1016/s0960-894x(02)00158-0 A549 2
11992780 10.1016/s0960-894x(02)00158-0 Telomerase reverse transcriptase 1
7699697 10.1021/jm00006a025 DNA topoisomerase 1 1
17157006 10.1016/j.bmcl.2006.11.024 Sterol O-acyltransferase 1 1
39129245 10.1021/acs.jmedchem.4c01514 A-375 1
11992780 10.1016/s0960-894x(02)00158-0 SGC-7901 1

Data from ChEMBL 36 via Core Engine