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Compound Detail

CHEMBL397309

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

Basic Information

ChEMBL ID CHEMBL397309
Name BETA-HYDROXYISOVALERYLSHIKONIN
Phase Preclinical
Structure Type MOL
InChI Key MXANJRGHSFELEJ-MRXNPFEDSA-N
12
Targets
19
Activities
2
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

388.4
MW (Da)
2.83
ALogP
7
HBA
3
HBD
121.1
PSA (Ų)
0.39
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H24O7
MW 388.42
Aromatic Rings 1
Heavy Atoms 28
NP-Likeness 2.19

Activity Summary

IC50 18 meas. best 6.43
Ki 1 meas. best 5.65

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 6.43 5.91 370.0 2
HepG2
CHEMBL395
 IC50 6.23 6.23 590.0 1
CCRF-CEM
CHEMBL382
 IC50 6.22 6.22 600.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.99 5.99 1020.0 1
Unchecked
CHEMBL612545
 Ki 5.65 5.65 2240.0 1
Unchecked
CHEMBL612545
 IC50 5.47 5.47 3400.0 1
MRC5
CHEMBL614181
 IC50 5.41 5.41 3900.0 1
MDA-MB-231
CHEMBL400
 IC50 5.34 5.34 4600.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.08 4.845 8300.0 4
DU-145
CHEMBL613508
 IC50 4.78 4.78 16800.0 1
U-251
CHEMBL615022
 IC50 4.63 4.63 23600.0 1
Neuraminidase
CHEMBL1795169
 IC50 4.39 4.39 40500.0 1
HeLa
CHEMBL399
 IC50 4.26 4.26 55000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 370.0 nM 6.43 Cytotoxicity against MDR1 Pgp under-expressing human HCT116 cells after 24 hrs b... 17949858
HepG2 IC50 = 590.0 nM 6.23 Cytotoxicity against MDR1 Pgp overexpressing human HepG2 cells after 24 hrs by M... 17949858
CCRF-CEM IC50 = 600.0 nM 6.22 Cytotoxicity against human CCRF-CEM cells after 72 hrs by XTT assay 22530779
Replicase polyprotein 1ab IC50 = 1020.0 nM 5.99 Inhibition of SARS-CoV-2 Main protease 38508325
Unchecked Ki = 2240.0 nM 5.65 Reversible inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-ter... 22300884
Unchecked IC50 = 3400.0 nM 5.47 Inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-terminal catal... 22300884
MRC5 IC50 = 3900.0 nM 5.41 Cytotoxicity against human MRC5 cells after 72 hrs by XTT assay 22530779
HCT-116 IC50 = 4100.0 nM 5.39 Cytotoxicity against human HCT116 cells after 72 hrs by XTT assay 22530779
MDA-MB-231 IC50 = 4600.0 nM 5.34 Cytotoxicity against human MDA-MB-231 cells after 72 hrs by XTT assay 22530779
NON-PROTEIN TARGET IC50 = 8300.0 nM 5.08 Cytotoxicity against human SBcl2 cells after 72 hrs by XTT assay 22530779
NON-PROTEIN TARGET IC50 = 12700.0 nM 4.9 Cytotoxicity against human WM9 cells after 72 hrs by XTT assay 22530779
NON-PROTEIN TARGET IC50 = 13000.0 nM 4.89 Cytotoxicity against human WM35 cells after 72 hrs by XTT assay 22530779
DU-145 IC50 = 16800.0 nM 4.78 Cytotoxicity against human DU145 cells by MTT assay 21689869
U-251 IC50 = 23600.0 nM 4.63 Cytotoxicity against human U251 cells after 72 hrs by XTT assay 22530779
NON-PROTEIN TARGET IC50 = 30900.0 nM 4.51 Cytotoxicity against human WM164 cells after 72 hrs by XTT assay 22530779
Neuraminidase IC50 = 40500.0 nM 4.39 Inhibition of recombinant influenza A virus H1N1 A/Bervig_Mission/1/18 sialidase... 22300884
HeLa IC50 = 55000.0 nM 4.26 Cytotoxicity against human HeLa cells by MTT assay 21689869

Literature References

PubMed DOI Target Context # Activities
22300884 10.1016/j.bmc.2012.01.011 Unchecked 8
- 10.1584/jpestics.23.54 Cladosporium herbarum 4
22530779 10.1021/np2006499 NON-PROTEIN TARGET 4
22300884 10.1016/j.bmc.2012.01.011 Neuraminidase 3
38508325 10.1016/j.bmcl.2024.129706 Replicase polyprotein 1ab 2
22530779 10.1021/np2006499 MRC5 2
22530779 10.1021/np2006499 MDA-MB-231 1
- 10.1584/jpestics.23.54 Tobacco mosaic virus 1
- 10.1584/jpestics.23.54 Nicotiana tabacum 1
22530779 10.1021/np2006499 HCT-116 1
22530779 10.1021/np2006499 U-251 1
17157006 10.1016/j.bmcl.2006.11.024 Sterol O-acyltransferase 1 1
22530779 10.1021/np2006499 CCRF-CEM 1
21689869 10.1016/j.ejmech.2011.05.065 HeLa 1
21689869 10.1016/j.ejmech.2011.05.065 DU-145 1
17949858 10.1016/j.ejmech.2007.08.009 HepG2 1
17949858 10.1016/j.ejmech.2007.08.009 HCT-116 1
17157006 10.1016/j.bmcl.2006.11.024 Sterol O-acyltransferase 2 1

Data from ChEMBL 36 via Core Engine