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Compound Detail

CHEMBL9470

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

Basic Information

ChEMBL ID CHEMBL9470
Name SHIKONIN
Phase Preclinical
Structure Type MOL
InChI Key NEZONWMXZKDMKF-SNVBAGLBSA-N
675
Targets
897
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

288.3
MW (Da)
2.12
ALogP
5
HBA
3
HBD
94.8
PSA (Ų)
0.58
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H16O5
MW 288.30
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 2.15

Activity Summary

IC50 896 meas. best 9.15
Ki 1 meas. best 4.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A101D
CHEMBL2366306
 IC50 9.15 9.15 0.7 1
TE-441-T
CHEMBL2366268
 IC50 8.65 8.65 2.2 1
NALM-6
CHEMBL614187
 IC50 8.55 8.55 2.8 1
SW1710
CHEMBL1075590
 IC50 8.54 8.54 2.9 1
ST486
CHEMBL2366293
 IC50 8.21 8.21 6.2 1
SK-UT-1
CHEMBL2366316
 IC50 8.13 8.13 7.4 1
A253 cell line
CHEMBL614255
 IC50 8.12 8.12 7.5 1
KU812 cell line
CHEMBL613997
 IC50 8.08 8.08 8.3 1
A-427
CHEMBL614515
 IC50 7.75 7.75 18.0 1
MZ1-PC
CHEMBL2366204
 IC50 7.71 7.71 19.3 1
NCI-H2009
CHEMBL1075528
 IC50 7.69 7.69 20.5 1
CAL-51
CHEMBL1075411
 IC50 7.68 7.68 20.9 1
SK-PN-DW
CHEMBL2366108
 IC50 7.44 7.44 36.5 1
GCIY
CHEMBL2366234
 IC50 7.44 7.44 36.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.4 5.988 40.0 5
KS-1
CHEMBL2366228
 IC50 7.38 7.38 41.5 1
MES-SA
CHEMBL614343
 IC50 7.38 7.38 41.3 1
IGROV-1
CHEMBL613984
 IC50 7.25 7.25 55.6 1
HMV-2 cell line
CHEMBL614826
 IC50 7.25 7.25 56.4 1
SW982
CHEMBL2366238
 IC50 7.22 6.385 60.2 2
NCI-H2052
CHEMBL1075531
 IC50 7.21 7.21 61.1 1
RT-112
CHEMBL614145
 IC50 7.15 7.15 70.4 1
AN3-CA
CHEMBL1075392
 IC50 7.1 7.1 79.7 1
A498
CHEMBL614516
 IC50 7.09 7.09 81.9 1
8-MG-BA
CHEMBL2366115
 IC50 7.07 7.07 85.6 1
HLE
CHEMBL1075464
 IC50 7.05 7.05 88.3 1
AM-38
CHEMBL2366192
 IC50 7.02 7.02 96.3 1
NCI-H1963
CHEMBL2366075
 IC50 7.0 7.0 100.1 1
NKM-1
CHEMBL2366133
 IC50 7.0 7.0 101.2 1
GR-ST
CHEMBL2366111
 IC50 6.99 6.99 102.2 1
MRK-nu-1
CHEMBL2366325
 IC50 6.99 6.99 101.9 1
A-431
CHEMBL614069
 IC50 6.97 6.97 107.0 1
SK-LMS-1
CHEMBL2366096
 IC50 6.96 6.96 108.4 1
MZ7-mel
CHEMBL2366138
 IC50 6.94 6.94 113.7 1
Kasumi 1
CHEMBL613988
 IC50 6.91 6.91 123.7 1
A204
CHEMBL614514
 IC50 6.9 6.9 126.5 1
M059J
CHEMBL1075494
 IC50 6.87 6.87 134.2 1
NCI-H2342
CHEMBL1075537
 IC50 6.87 6.87 134.4 1
KYSE-450
CHEMBL1075488
 IC50 6.86 6.86 138.2 1
Epidermal growth factor receptor
CHEMBL203
 IC50 6.86 6.86 139.2 1
SR
CHEMBL614300
 IC50 6.85 6.85 140.7 1
J82
CHEMBL614586
 IC50 6.85 6.85 142.6 1
NTERA-2-cl-D1
CHEMBL614206
 IC50 6.84 6.84 143.6 1
MEL-HO
CHEMBL1075500
 IC50 6.83 6.83 148.8 1
REH
CHEMBL2366320
 IC50 6.83 6.83 147.0 1
ACHN
CHEMBL614519
 IC50 6.83 6.83 146.4 1
IGR-1
CHEMBL1075479
 IC50 6.81 6.81 154.0 1
DEL
CHEMBL2366186
 IC50 6.81 6.81 153.8 1
RPMI-7951
CHEMBL612447
 IC50 6.81 6.81 156.1 1
Daoy
CHEMBL612519
 IC50 6.8 6.8 158.8 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
A101D IC50 = 0.7121 nM 9.15 SANGER: Inhibition of human A101D cell growth in a cell viability assay. -
TE-441-T IC50 = 2.238 nM 8.65 SANGER: Inhibition of human TE-441-T cell growth in a cell viability assay. -
NALM-6 IC50 = 2.797 nM 8.55 SANGER: Inhibition of human NALM-6 cell growth in a cell viability assay. -
SW1710 IC50 = 2.91 nM 8.54 SANGER: Inhibition of human SW1710 cell growth in a cell viability assay. -
ST486 IC50 = 6.179 nM 8.21 SANGER: Inhibition of human ST486 cell growth in a cell viability assay. -
SK-UT-1 IC50 = 7.438 nM 8.13 SANGER: Inhibition of human SK-UT-1 cell growth in a cell viability assay. -
A253 cell line IC50 = 7.493 nM 8.12 SANGER: Inhibition of human A253 cell growth in a cell viability assay. -
KU812 cell line IC50 = 8.306 nM 8.08 SANGER: Inhibition of human KU812 cell growth in a cell viability assay. -
A-427 IC50 = 17.99 nM 7.75 SANGER: Inhibition of human A427 cell growth in a cell viability assay. -
MZ1-PC IC50 = 19.28 nM 7.71 SANGER: Inhibition of human MZ1-PC cell growth in a cell viability assay. -
NCI-H2009 IC50 = 20.54 nM 7.69 SANGER: Inhibition of human NCI-H2009 cell growth in a cell viability assay. -
CAL-51 IC50 = 20.85 nM 7.68 SANGER: Inhibition of human CAL-51 cell growth in a cell viability assay. -
SK-PN-DW IC50 = 36.55 nM 7.44 SANGER: Inhibition of human SK-PN-DW cell growth in a cell viability assay. -
GCIY IC50 = 35.98 nM 7.44 SANGER: Inhibition of human GCIY cell growth in a cell viability assay. -
NON-PROTEIN TARGET IC50 = 40.0 nM 7.4 Cytotoxicity against human MIAPaCa2 cells assessed as reduction in cell growth a... 27080175
KS-1 IC50 = 41.5 nM 7.38 SANGER: Inhibition of human KS-1 cell growth in a cell viability assay. -
MES-SA IC50 = 41.32 nM 7.38 SANGER: Inhibition of human MES-SA cell growth in a cell viability assay. -
HMV-2 cell line IC50 = 56.4 nM 7.25 SANGER: Inhibition of human HMV-II cell growth in a cell viability assay. -
IGROV-1 IC50 = 55.61 nM 7.25 SANGER: Inhibition of human IGROV-1 cell growth in a cell viability assay. -
SW982 IC50 = 60.23 nM 7.22 SANGER: Inhibition of human SW982 cell growth in a cell viability assay. -

Literature References

PubMed DOI Target Context # Activities
32035399 10.1016/j.ejmech.2020.112105 HT-29 22
34922028 10.1016/j.bmcl.2021.128503 A549 15
29268130 10.1016/j.ejmech.2017.12.019 HeLa 11
36723914 10.1021/acs.jmedchem.2c01563 Pyruvate kinase PKM 10
39129245 10.1021/acs.jmedchem.4c01514 COP9 signalosome complex subunit 5 9
35367708 10.1016/j.ejmech.2022.114314 MCF7 8
22300884 10.1016/j.bmc.2012.01.011 Unchecked 8
35367708 10.1016/j.ejmech.2022.114314 A549 8
20970893 10.1016/j.ejmech.2010.09.068 Mus musculus 7
35367708 10.1016/j.ejmech.2022.114314 HeLa 7
12502328 10.1021/np010599w Staphylococcus aureus 6
12502328 10.1021/np010599w Enterococcus faecalis 6
30846253 10.1016/j.bmcl.2019.02.026 DNA topoisomerase II 6
35367708 10.1016/j.ejmech.2022.114314 Unchecked 6
35367708 10.1016/j.ejmech.2022.114314 L02 6
3760886 10.1021/np50045a014 Rattus norvegicus 6
34812616 10.1021/acs.jmedchem.1c01547 Unchecked 5
35367708 10.1016/j.ejmech.2022.114314 HepG2 5
36731272 10.1016/j.ejmech.2023.115166 NCI-H1975 5
2558164 10.1021/np50065a012 Unchecked 5

Data from ChEMBL 36 via Core Engine