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Compound Detail

CHEMBL267024

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

Basic Information

ChEMBL ID CHEMBL267024
Name DIMETHYLACRYLSHIKONIN
Phase Preclinical
Structure Type MOL
InChI Key BATBOVZTQBLKIL-QGZVFWFLSA-N
15
Targets
38
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

370.4
MW (Da)
3.64
ALogP
6
HBA
2
HBD
100.9
PSA (Ų)
0.36
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H22O6
MW 370.40
Aromatic Rings 1
Heavy Atoms 27
NP-Likeness 2.11

Activity Summary

IC50 37 meas. best 6.16
Ki 1 meas. best 5.76

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
WM793
CHEMBL4630705
 IC50 6.16 6.06 700.0 3
MUGMel1
CHEMBL4630715
 IC50 6.0 5.8933 1000.0 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.96 5.5625 1100.0 4
SBcl2
CHEMBL4630702
 IC50 5.96 5.89 1100.0 4
B16-F0
CHEMBL4296401
 IC50 5.92 5.92 1200.0 2
Unchecked
CHEMBL612545
 IC50 5.92 5.59 1200.0 4
MUGMel2
CHEMBL4630714
 IC50 5.77 5.46 1700.0 4
Unchecked
CHEMBL612545
 Ki 5.76 5.76 1750.0 1
CCRF-CEM
CHEMBL382
 IC50 5.72 5.72 1900.0 1
WM164
CHEMBL4630701
 IC50 5.62 5.41 2400.0 4
MRC5
CHEMBL614181
 IC50 5.62 5.32 2400.0 2
HCT-116
CHEMBL394
 IC50 4.7 4.7 20000.0 1
MDA-MB-231
CHEMBL400
 IC50 4.63 4.63 23200.0 1
U-251
CHEMBL615022
 IC50 4.51 4.51 30800.0 1
Neuraminidase
CHEMBL1795169
 IC50 4.33 4.33 47300.0 1
DNA topoisomerase 1
CHEMBL1781
 IC50 4.11 4.11 77000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
WM793 IC50 = 700.0 nM 6.16 Cytotoxicity against human WM793 cells harboring BRAF V600E mutant assessed as r... 31961147
WM793 IC50 = 800.0 nM 6.1 Cytotoxicity against human WM793 cells harboring BRAF V600E mutant assessed as r... 31961147
MUGMel1 IC50 = 1000.0 nM 6.0 Cytotoxicity against human MUGMel1 cells assessed as reduction in cell viability... 31961147
NON-PROTEIN TARGET IC50 = 1100.0 nM 5.96 Cytotoxicity against human SBcl2 cells after 72 hrs by XTT assay 22530779
MUGMel1 IC50 = 1100.0 nM 5.96 Cytotoxicity against human MUGMel1 cells assessed as reduction in cell viability... 31961147
SBcl2 IC50 = 1100.0 nM 5.96 Cytotoxicity against human SBcl2 cells harboring NRAS Q61I mutant assessed as re... 31961147
SBcl2 IC50 = 1100.0 nM 5.96 Antitumor activity against human SBcl2 cells assessed as reduction in cell viabi... 35367708
SBcl2 IC50 = 1200.0 nM 5.92 Cytotoxicity against human SBcl2 cells harboring NRAS Q61I mutant assessed as re... 31961147
WM793 IC50 = 1200.0 nM 5.92 Cytotoxicity against human WM793 cells harboring BRAF V600E mutant assessed as r... 31961147
B16-F0 IC50 = 1200.0 nM 5.92 Cytotoxicity against mouse B16F0 cells assessed as reduction in cell viability a... 31961147
B16-F0 IC50 = 1200.0 nM 5.92 Cytotoxicity against mouse B16F0 cells assessed as reduction in cell viability a... 31961147
Unchecked IC50 = 1200.0 nM 5.92 Antiproliferative activity against human TT cells assessed as inhibition of cell... 38458106
MUGMel2 IC50 = 1700.0 nM 5.77 Cytotoxicity against human MUGMel2 cells harboring NRAS pQ61K mutant assessed as... 31961147
Unchecked Ki = 1750.0 nM 5.76 Reversible inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-ter... 22300884
MUGMel1 IC50 = 1900.0 nM 5.72 Cytotoxicity against human MUGMel1 cells assessed as reduction in cell viability... 31961147
Unchecked IC50 = 1900.0 nM 5.72 Inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-terminal catal... 22300884
SBcl2 IC50 = 1900.0 nM 5.72 Cytotoxicity against human SBcl2 cells harboring NRAS Q61I mutant assessed as re... 31961147
CCRF-CEM IC50 = 1900.0 nM 5.72 Cytotoxicity against human CCRF-CEM cells after 72 hrs by XTT assay 22530779
NON-PROTEIN TARGET IC50 = 2300.0 nM 5.64 Cytotoxicity against human WM35 cells after 72 hrs by XTT assay 22530779
MUGMel2 IC50 = 2300.0 nM 5.64 Cytotoxicity against human MUGMel2 cells harboring NRAS pQ61K mutant assessed as... 31961147

Literature References

PubMed DOI Target Context # Activities
31961147 10.1021/acs.jnatprod.9b00719 SBcl2 29
31961147 10.1021/acs.jnatprod.9b00719 WM164 29
31961147 10.1021/acs.jnatprod.9b00719 MUGMel1 24
31961147 10.1021/acs.jnatprod.9b00719 MUGMel2 21
31961147 10.1021/acs.jnatprod.9b00719 WM793 21
22300884 10.1016/j.bmc.2012.01.011 Unchecked 8
22530779 10.1021/np2006499 Molecular identity unknown 6
31961147 10.1021/acs.jnatprod.9b00719 MRC5 5
22530779 10.1021/np2006499 NON-PROTEIN TARGET 4
22530779 10.1021/np2006499 Unchecked 4
22300884 10.1016/j.bmc.2012.01.011 Neuraminidase 3
22530779 10.1021/np2006499 MRC5 2
22530779 10.1021/np2006499 SBcl2 2
22530779 10.1021/np2006499 WM164 2
31961147 10.1021/acs.jnatprod.9b00719 ADMET 2
- 10.1584/jpestics.23.54 Tobacco mosaic virus 2
25127868 10.1016/j.bmcl.2014.07.012 Unchecked 2
31961147 10.1021/acs.jnatprod.9b00719 B16-F0 2
38458106 10.1016/j.ejmech.2024.116249 Unchecked 1
22530779 10.1021/np2006499 U-251 1

Data from ChEMBL 36 via Core Engine