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Compound Detail

CHEMBL9416

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

Basic Information

ChEMBL ID CHEMBL9416
Name ISOBUTYLSHIKONIN
Phase Preclinical
Structure Type MOL
InChI Key BVRYLTBIGIAADD-MRXNPFEDSA-N
10
Targets
16
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

358.4
MW (Da)
3.33
ALogP
6
HBA
2
HBD
100.9
PSA (Ų)
0.48
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 C20H22O6
MW 358.39
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 2.09

Activity Summary

IC50 15 meas. best 7.3
Ki 1 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
U-937
CHEMBL612794
 IC50 7.3 7.3 50.0 1
HepG2
CHEMBL395
 IC50 6.66 5.86 220.0 2
Unchecked
CHEMBL612545
 Ki 6.58 6.58 260.0 1
HCT-116
CHEMBL394
 IC50 6.47 6.115 340.0 2
COP9 signalosome complex subunit 5
CHEMBL4105809
 IC50 6.22 6.075 600.0 2
A-375
CHEMBL613859
 IC50 5.77 5.77 1710.0 1
Ca9-22
CHEMBL1075404
 IC50 5.75 5.725 1800.0 2
Unchecked
CHEMBL612545
 IC50 5.54 5.54 2900.0 1
Neuraminidase
CHEMBL1795169
 IC50 4.39 4.39 40500.0 1
Sterol O-acyltransferase 2
CHEMBL4465
 IC50 4.24 4.24 57500.0 1
DNA topoisomerase 1
CHEMBL1781
 IC50 4.08 4.08 84000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
U-937 IC50 = 50.0 nM 7.3 Cytotoxicity against human U-937 cells assessed as reduction in cell viability i... 38458106
HepG2 IC50 = 220.0 nM 6.66 Cytotoxicity against MDR1 Pgp overexpressing human HepG2 cells after 24 hrs by M... 17949858
Unchecked Ki = 260.0 nM 6.58 Reversible inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-ter... 22300884
HCT-116 IC50 = 340.0 nM 6.47 Cytotoxicity against MDR1 Pgp under-expressing human HCT116 cells after 24 hrs b... 17949858
COP9 signalosome complex subunit 5 IC50 = 600.0 nM 6.22 Inhibition of N-terminal His6-tagged CSN5 (2 to 257 residues) (unknown origin) t... 39129245
COP9 signalosome complex subunit 5 IC50 = 1170.0 nM 5.93 Inhibition of N-terminal His6-tagged CSN5 (2 to 257 residues) (unknown origin) t... 39129245
A-375 IC50 = 1710.0 nM 5.77 Antiproliferative activity against human A-375 cells assessed as inhibition of c... 39129245
HCT-116 IC50 = 1730.0 nM 5.76 Antiproliferative activity against human HCT-116 cells assessed as inhibition of... 39129245
Ca9-22 IC50 = 1800.0 nM 5.75 Cytotoxicity against human Ca9-22 cells assessed as reduction in cell viability ... 35367708
Ca9-22 IC50 = 1980.0 nM 5.7 Cytotoxicity against human Ca9-22 cells assessed as reduction in cell viability ... 35367708
Unchecked IC50 = 2900.0 nM 5.54 Inhibition of Clostridium perfringens ATCC 10543 sialidase Nan1 c-terminal catal... 22300884
HepG2 IC50 = 8730.0 nM 5.06 Antiproliferative activity against human HepG2 cells assessed as inhibition of c... 39129245
Neuraminidase IC50 = 40500.0 nM 4.39 Inhibition of recombinant influenza A virus H1N1 A/Bervig_Mission/1/18 sialidase... 22300884
Sterol O-acyltransferase 2 IC50 = 57500.0 nM 4.24 Inhibition of human ACAT2 expressed in Hi5 cells 17157006
DNA topoisomerase 1 IC50 = 84000.0 nM 4.08 Inhibitory activity against DNA topoisomerase-1 obtained from Hela cells 7699697

Literature References

PubMed DOI Target Context # Activities
22300884 10.1016/j.bmc.2012.01.011 Unchecked 8
22300884 10.1016/j.bmc.2012.01.011 Neuraminidase 3
- 10.1584/jpestics.23.54 Tobacco mosaic virus 2
35367708 10.1016/j.ejmech.2022.114314 Ca9-22 2
39129245 10.1021/acs.jmedchem.4c01514 COP9 signalosome complex subunit 5 2
7699697 10.1021/jm00006a025 DNA topoisomerase 1 1
17157006 10.1016/j.bmcl.2006.11.024 Sterol O-acyltransferase 1 1
17157006 10.1016/j.bmcl.2006.11.024 Sterol O-acyltransferase 2 1
17949858 10.1016/j.ejmech.2007.08.009 HCT-116 1
17949858 10.1016/j.ejmech.2007.08.009 HepG2 1
38458106 10.1016/j.ejmech.2024.116249 U-937 1
39129245 10.1021/acs.jmedchem.4c01514 HCT-116 1
39129245 10.1021/acs.jmedchem.4c01514 HepG2 1
39129245 10.1021/acs.jmedchem.4c01514 A-375 1

Data from ChEMBL 36 via Core Engine