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Compound Detail

CHEMBL476220

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O=C(/C=C/c1ccc(F)cc1)/C=C/c1ccc(F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL476220
Phase Preclinical
Structure Type MOL
InChI Key BNHFGYIPXPENKA-YDWXAUTNSA-N
9
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

270.3
MW (Da)
4.26
ALogP
1
HBA
0
HBD
17.1
PSA (Ų)
0.76
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H12F2O
MW 270.28
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.19

Activity Summary

IC50 11 meas. best 7.0
EC50 1 meas. best 5.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
17-beta-hydroxysteroid dehydrogenase type 3
CHEMBL1075158
 IC50 7.0 6.24 100.0 2
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL2391
 IC50 6.64 6.64 229.0 1
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 IC50 6.29 6.29 507.0 1
Trypanosoma brucei
CHEMBL612849
 EC50 5.85 5.85 1420.0 1
HT-29
CHEMBL384
 IC50 5.03 5.03 9350.0 1
PANC-1
CHEMBL614139
 IC50 4.9 4.9 12530.0 1
PC-3
CHEMBL390
 IC50 4.82 4.82 15190.0 2
HL-60
CHEMBL383
 IC50 4.02 4.02 94600.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.0 4.0 98800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
17-beta-hydroxysteroid dehydrogenase type 3 IC50 = 100.0 nM 7.0 Inhibition of 17beta-HSD3 in Sprague-Dawley rat laydig cells 20346654
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 229.0 nM 6.64 Inhibition of 11beta-HSD1 in Sprague-Dawley rat leydig cells at 100 uM 23800686
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 507.0 nM 6.29 Inhibition of human 11beta-HSD1 transfected in CHOP cells 23800686
Trypanosoma brucei EC50 = 1420.0 nM 5.85 Antitrypanosomal activity against Trypanosoma brucei Lister 427 assessed as para... 36608774
17-beta-hydroxysteroid dehydrogenase type 3 IC50 = 3300.0 nM 5.48 Inhibition of 17beta-HSD3 in Sprague-Dawley rat testis microsomes 20346654
HT-29 IC50 = 9350.0 nM 5.03 Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay 22551677
PANC-1 IC50 = 12530.0 nM 4.9 Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay 22551677
PC-3 IC50 = 15200.0 nM 4.82 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 19243951
PC-3 IC50 = 15190.0 nM 4.82 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 22551677
HL-60 IC50 = 94600.0 nM 4.02 Cytotoxicity against human HL60 cells after 72 hrs by MTT assay 19243951
NON-PROTEIN TARGET IC50 = 98800.0 nM 4.0 Cytotoxicity against human LS 174T cells after 72 hrs by MTT assay 19243951

Literature References

PubMed DOI Target Context # Activities
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase 1 5
30108820 10.1039/C6MD00649C Pichia kudriavzevii 3
30108820 10.1039/C6MD00649C Candida tropicalis 3
30108820 10.1039/C6MD00649C Candida albicans 3
20346654 10.1016/j.bmcl.2010.02.089 17-beta-hydroxysteroid dehydrogenase type 3 3
30108820 10.1039/C6MD00649C HUVEC 2
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase type 2 2
21493068 10.1016/j.bmcl.2011.03.037 Plasmodium falciparum 2
21493068 10.1016/j.bmcl.2011.03.037 HeLa 1
36608774 10.1016/j.bmcl.2023.129123 HEK293 1
22551677 10.1016/j.ejmech.2012.04.005 HT-29 1
22551677 10.1016/j.ejmech.2012.04.005 PANC-1 1
22551677 10.1016/j.ejmech.2012.04.005 PC-3 1
19243951 10.1016/j.bmc.2008.10.044 HL-60 1
19359068 10.1016/j.ejmech.2009.03.020 Tyrosinase 1
19359068 10.1016/j.ejmech.2009.03.020 Radical scavenging activity 1
19359068 10.1016/j.ejmech.2009.03.020 No relevant target 1
19359068 10.1016/j.ejmech.2009.03.020 RAW264.7 1
19243951 10.1016/j.bmc.2008.10.044 No relevant target 1
19243951 10.1016/j.bmc.2008.10.044 PC-3 1

Data from ChEMBL 36 via Core Engine