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Compound Detail

CHEMBL89828

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C=CCc1ccc(OC)c(-c2ccc(OC)c(CC=C)c2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL89828
Phase Preclinical
Structure Type MOL
InChI Key GDCJELDNRAWYTE-UHFFFAOYSA-N
6
Targets
6
Activities
3
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

294.4
MW (Da)
4.83
ALogP
2
HBA
0
HBD
18.5
PSA (Ų)
0.68
QED
0
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 C20H22O2
MW 294.39
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 0.31

Activity Summary

IC50 4 meas. best 5.11
EC50 1 meas. best 4.38
Ki 1 meas. best 5.86

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 2
CHEMBL253
 Ki 5.86 5.86 1375.0 1
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 5.11 5.11 7700.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 4.94 4.94 11400.0 1
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 4.82 4.82 15000.0 1
RAW264.7
CHEMBL612557
 IC50 4.4 4.4 40000.0 1
GABA-A receptor; GABA-A site (alpha1/beta2 interface)
CHEMBL1907597
 EC50 4.38 4.38 42100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 2 Ki = 1375.0 nM 5.86 Displacement of [3H]CP55940 from human CB2 receptor expressed in CHO cell membra... 27078864
Prostaglandin G/H synthase 2 IC50 = 7700.0 nM 5.11 Inhibition of COX2 in sheep placental vesicle by enzyme immunoassay 19481465
Prostaglandin G/H synthase 1 IC50 = 11400.0 nM 4.94 Inhibition of COX1 in ram seminal vesicle by enzyme immunoassay 19481465
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 15000.0 nM 4.82 Inhibition of 5LOX-mediated LTB4 formation in stimulated human polymorphonuclear... 19481465
RAW264.7 IC50 = 40000.0 nM 4.4 Inhibition of LPS-induced NO production in mouse RAW264.7 cells after 24 hrs by ... 22494844
GABA-A receptor; GABA-A site (alpha1/beta2 interface) EC50 = 42100.0 nM 4.38 Modulation of GABA Aalpha1beta2 receptor expressed in Xenopus laevis oocytes ass... 21699169

Literature References

PubMed DOI Target Context # Activities
21699169 10.1021/jm200186n GABA-A receptor; GABA-A site (alpha1/beta2 interface) 3
19481465 10.1016/j.bmc.2009.05.018 Prostaglandin G/H synthase 1 2
19481465 10.1016/j.bmc.2009.05.018 Prostaglandin G/H synthase 2 2
19481465 10.1016/j.bmc.2009.05.018 Polyunsaturated fatty acid 5-lipoxygenase 2
15109665 10.1016/j.bmcl.2004.02.067 Rattus norvegicus 2
22494844 10.1016/j.bmc.2012.03.028 Prostaglandin G/H synthase 2 2
22494844 10.1016/j.bmc.2012.03.028 RAW264.7 2
27078864 10.1016/j.ejmech.2016.03.072 Cannabinoid receptor 2 2
31831382 10.1016/j.bmcl.2019.126849 I10 1
31831382 10.1016/j.bmcl.2019.126849 CNE2Z 1
31831382 10.1016/j.bmcl.2019.126849 MCF7 1
31278004 10.1016/j.bmc.2019.06.042 No relevant target 1
27078864 10.1016/j.ejmech.2016.03.072 Cannabinoid receptor 1 1
21853991 10.1021/jm200830u NON-PROTEIN TARGET 1
21853991 10.1021/jm200830u HepG2 1
21853991 10.1021/jm200830u A549 1
21853991 10.1021/jm200830u HUVEC 1
21699169 10.1021/jm200186n No relevant target 1

Data from ChEMBL 36 via Core Engine