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Compound Detail

CHEMBL240545

ROTENOLONE
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C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@]2(O)C3=O)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL240545
Name ROTENOLONE
Phase Preclinical
Structure Type MOL
InChI Key JFVKWCYZKMUTLH-AYPBNUJASA-N
11
Targets
16
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

410.4
MW (Da)
2.81
ALogP
7
HBA
1
HBD
83.5
PSA (Ų)
0.78
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 C23H22O7
MW 410.42
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness 2.18

Activity Summary

IC50 16 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
U-937
CHEMBL612794
 IC50 7.16 6.55 70.0 3
HT-29
CHEMBL384
 IC50 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
 IC50 6.89 6.89 130.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.7 6.7 200.0 1
697
CHEMBL2366253
 IC50 6.3 6.23 500.0 2
A2780
CHEMBL614004
 IC50 6.02 6.02 950.0 1
BT-549
CHEMBL614072
 IC50 5.8 5.8 1600.0 1
NCI-H460
CHEMBL396
 IC50 5.7 5.7 2000.0 1
Raji
CHEMBL614628
 IC50 5.62 5.435 2400.0 2
DU-145
CHEMBL613508
 IC50 5.57 5.57 2700.0 1
HCC 2998
CHEMBL613855
 IC50 5.54 5.54 2900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
U-937 IC50 = 70.0 nM 7.16 Antiproliferative activity against human U937 cells after 48 hrs by WST-8 assay 17158054
U-937 IC50 = 90.0 nM 7.05 Antiproliferative activity against human U937 cells after 72 hrs by WST-8 assay 17158054
HT-29 IC50 = 100.0 nM 7.0 Cytotoxicity against human HT-29 cells after 72 hrs by SRB assay 23895019
Unchecked IC50 = 130.0 nM 6.89 Inhibition of complex 1 in bovine heart mitochondrial membranes in presence of N... 32459967
NON-PROTEIN TARGET IC50 = 200.0 nM 6.7 Cytotoxicity against mouse Hepa-1c1c7 cells 23895019
697 IC50 = 500.0 nM 6.3 Cytotoxicity against human 697 cells after 72 hrs by MTS assay 23895019
697 IC50 = 700.0 nM 6.16 Cytotoxicity against human 697 cells after 48 hrs by MTS assay 23895019
A2780 IC50 = 950.0 nM 6.02 Antiproliferative activity against human A2780 cells after 96 hrs by CellTiter-G... 20804165
BT-549 IC50 = 1600.0 nM 5.8 Antiproliferative activity against human BT549 cells after 96 hrs by CellTiter-G... 20804165
NCI-H460 IC50 = 2000.0 nM 5.7 Antiproliferative activity against human NCI-H460 cells after 96 hrs by CellTite... 20804165
Raji IC50 = 2400.0 nM 5.62 Cytotoxicity against human Raji cells after 72 hrs by MTS assay 23895019
DU-145 IC50 = 2700.0 nM 5.57 Antiproliferative activity against human DU145 cells after 96 hrs by CellTiter-G... 20804165
HCC 2998 IC50 = 2900.0 nM 5.54 Antiproliferative activity against human HCC2998 cells after 96 hrs by CellTiter... 20804165
U-937 IC50 = 3600.0 nM 5.44 Antiproliferative activity against human U937 cells after 24 hrs by WST-8 assay 17158054
Raji IC50 = 5600.0 nM 5.25 Cytotoxicity against human Raji cells after 48 hrs by MTS assay 23895019

Literature References

PubMed DOI Target Context # Activities
17158054 10.1016/j.bmc.2006.09.024 HT-1080 30
32459967 10.1021/acs.jnatprod.9b01224 Unchecked 4
17158054 10.1016/j.bmc.2006.09.024 U-937 3
32459967 10.1021/acs.jnatprod.9b01224 LNCaP C4-2B 3
32459967 10.1021/acs.jnatprod.9b01224 LNCaP C4-2 3
23895019 10.1021/np400567c Mus musculus 2
23895019 10.1021/np400567c HT-29 2
23895019 10.1021/np400567c 697 2
23895019 10.1021/np400567c Unchecked 2
23895019 10.1021/np400567c ADMET 2
23895019 10.1021/np400567c Raji 2
30910460 10.1016/j.bmcl.2019.03.024 Cholinesterase 2
30910460 10.1016/j.bmcl.2019.03.024 Acetylcholinesterase 2
32459967 10.1021/acs.jnatprod.9b01224 PNT2 2
20804165 10.1021/np100430r A2780 1
20804165 10.1021/np100430r BT-549 1
20804165 10.1021/np100430r DU-145 1
11975515 10.1021/np010126p Candida albicans 1
11975515 10.1021/np010126p Bacteroides fragilis 1
11975515 10.1021/np010126p Bacillus subtilis 1

Data from ChEMBL 36 via Core Engine