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Compound Detail

CHEMBL482409

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O=C1/C(=C/c2ccc(O)cc2)CCC/C1=C\c1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL482409
Phase Preclinical
Structure Type MOL
InChI Key MGXGEFQCJBBKND-UNZYHPAISA-N
13
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

306.4
MW (Da)
4.32
ALogP
3
HBA
2
HBD
57.5
PSA (Ų)
0.81
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H18O3
MW 306.36
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.06

Activity Summary

IC50 16 meas. best 9.03
EC50 1 meas. best 6.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tissue factor
CHEMBL4081
 IC50 9.03 9.03 0.9 1
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 IC50 6.71 6.21 195.0 2
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL2391
 IC50 6.2 6.2 633.0 1
Molecular identity unknown
CHEMBL612546
 EC50 6.1 6.1 800.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.0 6.0 1000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.97 5.97 1060.0 1
Unchecked
CHEMBL612545
 IC50 5.26 5.26 5520.0 1
CCRF-CEM
CHEMBL382
 IC50 5.17 5.165 6840.0 2
L1210
CHEMBL386
 IC50 4.97 4.92 10700.0 2
HT-29
CHEMBL384
 IC50 4.93 4.93 11700.0 1
PC-3
CHEMBL390
 IC50 4.88 4.88 13250.0 1
PANC-1
CHEMBL614139
 IC50 4.88 4.88 13210.0 1
RAW264.7
CHEMBL612557
 IC50 4.38 4.38 41590.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tissue factor IC50 = 0.94 nM 9.03 Inhibition of tissue factor in Homo sapiens (human) THP1-cells using factor 10a ... -
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 195.0 nM 6.71 Inhibition of human 11beta-HSD1 transfected in CHOP cells 23800686
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 633.0 nM 6.2 Inhibition of 11beta-HSD1 in Sprague-Dawley rat leydig cells at 100 uM 23800686
Molecular identity unknown EC50 = 800.0 nM 6.1 Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells after 24 hrs by firef... 24275249
Cytochrome P450 2C9 IC50 = 1000.0 nM 6.0 Inhibition of human recombinant CYP2C9 18249473
NON-PROTEIN TARGET IC50 = 1060.0 nM 5.97 Antiproliferative activity against human Molt4/C8 cells assessed as cell surviva... 26727215
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 1944.0 nM 5.71 Inhibition of 11beta-HSD1 in human liver microsomes using [3H]-cortisone as subs... 23800686
Unchecked IC50 = 5520.0 nM 5.26 Cytotoxicity against human Molt4/C8 cells assessed as growth inhibition after 72... 28238612
CCRF-CEM IC50 = 6840.0 nM 5.17 Cytotoxicity against human CEM cells assessed as growth inhibition after 72 hrs ... 28238612
CCRF-CEM IC50 = 6960.0 nM 5.16 Antiproliferative activity against human CEM cells assessed as cell survival aft... 26727215
L1210 IC50 = 10700.0 nM 4.97 Antiproliferative activity against mouse L1210 cells assessed as cell survival a... 26727215
HT-29 IC50 = 11700.0 nM 4.93 Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay 22551677
PC-3 IC50 = 13250.0 nM 4.88 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 22551677
PANC-1 IC50 = 13210.0 nM 4.88 Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay 22551677
L1210 IC50 = 13500.0 nM 4.87 Cytotoxicity against mouse L1210 cells assessed as growth inhibition after 48 hr... 28238612
RAW264.7 IC50 = 41590.0 nM 4.38 Anti-inflammatory activity in Mus musculus (mouse) RAW264.7 cells assessed as in... -

Literature References

PubMed DOI Target Context # Activities
24275249 10.1016/j.ejmech.2013.10.073 Molecular identity unknown 10
26727215 10.1021/acs.jmedchem.5b01706 NON-PROTEIN TARGET 6
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase 1 5
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2C9 3
26727215 10.1021/acs.jmedchem.5b01706 HSC-4 3
26727215 10.1021/acs.jmedchem.5b01706 HL-60 3
26727215 10.1021/acs.jmedchem.5b01706 HSC-2 3
26727215 10.1021/acs.jmedchem.5b01706 HSC-3 3
20346654 10.1016/j.bmcl.2010.02.089 17-beta-hydroxysteroid dehydrogenase type 3 3
26727215 10.1021/acs.jmedchem.5b01706 ADMET 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
18336957 10.1016/j.ejmech.2008.01.031 J774.A1 2
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2B6 2
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2D6 2
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 3A4 2
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase type 2 2
19359068 10.1016/j.ejmech.2009.03.020 Tyrosinase 1
19359068 10.1016/j.ejmech.2009.03.020 RAW264.7 1
22551677 10.1016/j.ejmech.2012.04.005 PC-3 1
22551677 10.1016/j.ejmech.2012.04.005 PANC-1 1

Data from ChEMBL 36 via Core Engine