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Compound Detail

CHEMBL129134

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

Basic Information

ChEMBL ID CHEMBL129134
Phase Preclinical
Structure Type MOL
InChI Key FTEGUKWEUQPKIS-YDWXAUTNSA-N
18
Targets
24
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

266.3
MW (Da)
3.39
ALogP
3
HBA
2
HBD
57.5
PSA (Ų)
0.83
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C17H14O3
MW 266.30
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.52

Activity Summary

IC50 23 meas. best 8.59
EC50 1 meas. best 5.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tissue factor
CHEMBL4081
 IC50 8.59 8.59 2.6 1
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL4235
 IC50 6.08 5.715 832.0 2
11-beta-hydroxysteroid dehydrogenase 1
CHEMBL2391
 IC50 6.01 6.01 986.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.75 5.75 1800.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.7 5.7 2000.0 1
Molecular identity unknown
CHEMBL612546
 EC50 5.5 5.5 3200.0 1
CCRF-CEM
CHEMBL382
 IC50 5.47 5.47 3380.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.43 5.43 3690.0 1
MDA-MB-231
CHEMBL400
 IC50 5.41 5.41 3900.0 1
LNCaP
CHEMBL612518
 IC50 5.24 5.24 5800.0 1
MCF7
CHEMBL387
 IC50 5.16 5.16 6900.0 1
L1210
CHEMBL386
 IC50 5.11 5.11 7740.0 1
HT-29
CHEMBL384
 IC50 5.03 5.03 9380.0 1
PC-3
CHEMBL390
 IC50 5.02 4.78 9500.0 3
PANC-1
CHEMBL614139
 IC50 4.87 4.87 13590.0 1
HL-60
CHEMBL383
 IC50 4.38 4.38 41500.0 1
Tyrosinase
CHEMBL1973
 IC50 4.1 4.1 79050.0 1
Human immunodeficiency virus type 1 integrase
CHEMBL3471
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tissue factor IC50 = 2.58 nM 8.59 Inhibition of tissue factor in Homo sapiens (human) THP1-cells using factor 10a ... -
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 832.0 nM 6.08 Inhibition of human 11beta-HSD1 transfected in CHOP cells 23800686
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 986.0 nM 6.01 Inhibition of 11beta-HSD1 in Sprague-Dawley rat leydig cells at 100 uM 23800686
Cytochrome P450 2C9 IC50 = 1800.0 nM 5.75 Inhibition of human recombinant CYP2C9 18249473
Cytochrome P450 2D6 IC50 = 2000.0 nM 5.7 Inhibition of human recombinant CYP2D6 18249473
Molecular identity unknown EC50 = 3200.0 nM 5.5 Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells after 24 hrs by firef... 24275249
CCRF-CEM IC50 = 3380.0 nM 5.47 Antiproliferative activity against human CEM cells assessed as cell survival aft... 26727215
NON-PROTEIN TARGET IC50 = 3690.0 nM 5.43 Antiproliferative activity against human Molt4/C8 cells assessed as cell surviva... 26727215
MDA-MB-231 IC50 = 3900.0 nM 5.41 Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by MTT as... 19249204
11-beta-hydroxysteroid dehydrogenase 1 IC50 = 4423.0 nM 5.35 Inhibition of 11beta-HSD1 in human liver microsomes using [3H]-cortisone as subs... 23800686
LNCaP IC50 = 5800.0 nM 5.24 Antiproliferative activity against human LNCAP cells after 72 hrs by MTT assay 19249204
MCF7 IC50 = 6900.0 nM 5.16 Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay 19249204
L1210 IC50 = 7740.0 nM 5.11 Antiproliferative activity against mouse L1210 cells assessed as cell survival a... 26727215
HT-29 IC50 = 9380.0 nM 5.03 Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay 22551677
PC-3 IC50 = 9500.0 nM 5.02 Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay 19249204
PC-3 IC50 = 9680.0 nM 5.01 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 22551677
PANC-1 IC50 = 13590.0 nM 4.87 Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay 22551677
HL-60 IC50 = 41500.0 nM 4.38 Cytotoxicity against human HL60 cells after 72 hrs by MTT assay 19243951
PC-3 IC50 = 48900.0 nM 4.31 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 19243951
Tyrosinase IC50 = 79050.0 nM 4.1 Inhibition of tyrosinase 19359068

Literature References

PubMed DOI Target Context # Activities
24275249 10.1016/j.ejmech.2013.10.073 Molecular identity unknown 10
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase 1 5
26727215 10.1021/acs.jmedchem.5b01706 NON-PROTEIN TARGET 5
24275249 10.1016/j.ejmech.2013.10.073 U2OS 4
30108820 10.1039/C6MD00649C Candida tropicalis 3
20346654 10.1016/j.bmcl.2010.02.089 17-beta-hydroxysteroid dehydrogenase type 3 3
26727215 10.1021/acs.jmedchem.5b01706 HSC-3 3
26727215 10.1021/acs.jmedchem.5b01706 HSC-2 3
30108820 10.1039/C6MD00649C Candida albicans 3
26727215 10.1021/acs.jmedchem.5b01706 ADMET 3
26727215 10.1021/acs.jmedchem.5b01706 HSC-4 3
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2D6 3
18249473 10.1016/j.ejmech.2007.10.034 Cytochrome P450 2C9 3
26727215 10.1021/acs.jmedchem.5b01706 HL-60 3
30108820 10.1039/C6MD00649C Pichia kudriavzevii 3
27996267 10.1021/acs.jmedchem.6b00788 No relevant target 2
23800686 10.1016/j.bmcl.2013.05.080 11-beta-hydroxysteroid dehydrogenase type 2 2
30108820 10.1039/C6MD00649C HUVEC 2
18336957 10.1016/j.ejmech.2008.01.031 J774.A1 2
19249204 10.1016/j.bmcl.2009.01.104 PC-3 1

Data from ChEMBL 36 via Core Engine