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Compound Detail

CHEMBL243796

KURARINONE
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C=C(C)C(CC=C(C)C)Cc1c(O)cc(OC)c2c1O[C@H](c1ccc(O)cc1O)CC2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL243796
Name KURARINONE
Phase Preclinical
Structure Type MOL
InChI Key LTTQKYMNTNISSZ-KESSSICBSA-N
11
Targets
14
Activities
3
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

438.5
MW (Da)
5.61
ALogP
6
HBA
3
HBD
96.2
PSA (Ų)
0.49
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C26H30O6
MW 438.52
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness 2.55

Activity Summary

IC50 10 meas. best 6.22
EC50 2 meas. best 5.78
Ki 2 meas. best 5.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 6.22 6.22 600.0 1
Estrogen receptor
CHEMBL206
 EC50 5.78 5.56 1660.0 2
Sodium/glucose cotransporter 2
CHEMBL3884
 IC50 5.77 5.77 1700.0 1
Beta-secretase 1
CHEMBL4822
 IC50 5.48 5.48 3300.0 1
Beta-secretase 1
CHEMBL4822
 Ki 5.14 5.14 7200.0 1
Sodium/glucose cotransporter 1
CHEMBL4979
 IC50 4.98 4.98 10400.0 1
Sterol O-acyltransferase 1
CHEMBL2782
 IC50 4.96 4.96 10900.0 1
Diacylglycerol O-acyltransferase 1
CHEMBL6129
 IC50 4.96 4.96 10900.0 1
Unchecked
CHEMBL612545
 IC50 4.82 4.82 15100.0 1
HL-60
CHEMBL383
 IC50 4.73 4.73 18500.0 1
Unchecked
CHEMBL612545
 Ki 4.73 4.73 18800.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.65 4.65 22200.0 1
RAW264.7
CHEMBL612557
 IC50 4.58 4.58 26600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 1 IC50 = 600.0 nM 6.22 Inhibition of COX1 16038536
Estrogen receptor EC50 = 1660.0 nM 5.78 Estrogenic activity at estrogen receptor in human Ishikawa Var-1 cells assessed ... 15568770
Sodium/glucose cotransporter 2 IC50 = 1700.0 nM 5.77 Inhibition of human SGLT2 expressed in COS1 cells assessed as [14C]methyl-alpha-... 17374486
Beta-secretase 1 IC50 = 3300.0 nM 5.48 Inhibition of human BACE1 18565755
Estrogen receptor EC50 = 4600.0 nM 5.34 Estrogenic activity at human estrogen receptor expressing Saccharomyces cerevisi... 15568770
Beta-secretase 1 Ki = 7200.0 nM 5.14 Inhibition of human BACE1 18565755
Sodium/glucose cotransporter 1 IC50 = 10400.0 nM 4.98 Inhibition of human SGLT1 expressed in COS1 cells assessed as [14C]methyl-alpha-... 17374486
Diacylglycerol O-acyltransferase 1 IC50 = 10900.0 nM 4.96 Inhibition of DGAT in rat liver microsomes 23141914
Sterol O-acyltransferase 1 IC50 = 10900.0 nM 4.96 Inhibition of human macrophage ACAT expressed in human HepG2 cells using [14C]ol... 23419736
Unchecked IC50 = 15100.0 nM 4.82 Inhibition of Clostridium perfringens neuraminidase 18938076
HL-60 IC50 = 18500.0 nM 4.73 Cytotoxicity against human HL60 cells after 96 hrs by MTT assay 10843587
Unchecked Ki = 18800.0 nM 4.73 Inhibition of Clostridium perfringens neuraminidase by Lineweaver-Burke plot 18938076
NON-PROTEIN TARGET IC50 = 22200.0 nM 4.65 Cytotoxicity against human MCF7/6 cells after 72 hrs by SRB assay 15568770
RAW264.7 IC50 = 26600.0 nM 4.58 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 26073007

Literature References

PubMed DOI Target Context # Activities
10654410 10.1021/np990051d Unchecked 6
18565755 10.1016/j.bmc.2008.05.080 Beta-secretase 1 4
15568770 10.1021/np040069a NON-PROTEIN TARGET 3
17374486 10.1016/j.bmc.2007.03.011 Sodium/glucose cotransporter 2 2
26073007 10.1016/j.bmcl.2015.05.062 RAW264.7 2
18938076 10.1016/j.bmcl.2008.10.033 Unchecked 2
15568770 10.1021/np040069a Estrogen receptor 2
17374486 10.1016/j.bmc.2007.03.011 Sodium/glucose cotransporter 1 2
10654410 10.1021/np990051d Staphylococcus aureus 1
10654410 10.1021/np990051d Bacillus subtilis 1
16038536 10.1021/np049655u Prostaglandin G/H synthase 1 1
10843587 10.1021/np990567x HL-60 1
23141914 10.1016/j.bmcl.2012.10.046 Diacylglycerol O-acyltransferase 1 1
23419736 10.1016/j.ejmech.2013.01.020 Sterol O-acyltransferase 1 1
31810785 10.1016/j.ejmech.2019.111892 Bacillus cereus 1
31810785 10.1016/j.ejmech.2019.111892 Bacillus subtilis 1
31810785 10.1016/j.ejmech.2019.111892 Staphylococcus aureus 1
31810785 10.1016/j.ejmech.2019.111892 Tyrosinase 1

Data from ChEMBL 36 via Core Engine