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Compound Detail

CHEMBL89700

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

Basic Information

ChEMBL ID CHEMBL89700
Name METHYLHONOKIOL
Phase Preclinical
Structure Type MOL
InChI Key OQFHJKZVOALSPV-UHFFFAOYSA-N
20
Targets
29
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

280.4
MW (Da)
4.52
ALogP
2
HBA
1
HBD
29.5
PSA (Ų)
0.79
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H20O2
MW 280.37
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness 0.70

Activity Summary

IC50 27 meas. best 7.22
EC50 1 meas. best 4.57
Ki 1 meas. best 7.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cannabinoid receptor 2
CHEMBL253
 Ki 7.36 7.36 44.0 1
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 7.22 7.22 60.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 7.0 7.0 100.0 1
A549
CHEMBL392
 IC50 5.91 5.46 1240.0 3
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 5.82 5.82 1500.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.09 4.6967 8180.0 3
HT-29
CHEMBL384
 IC50 4.85 4.7267 14130.0 3
A2780
CHEMBL614004
 IC50 4.83 4.83 14670.0 1
PANC-1
CHEMBL614139
 IC50 4.78 4.78 16730.0 1
HepG2
CHEMBL395
 IC50 4.76 4.51 17470.0 2
PC-3
CHEMBL390
 IC50 4.75 4.75 17870.0 1
RAW264.7
CHEMBL612557
 IC50 4.75 4.66 18000.0 2
L02
CHEMBL4296457
 IC50 4.62 4.62 23940.0 1
UACC-903
CHEMBL612446
 IC50 4.62 4.52 24130.0 2
MCF7
CHEMBL387
 IC50 4.61 4.61 24710.0 1
CNE2Z
CHEMBL4632328
 IC50 4.59 4.59 25530.0 1
I10
CHEMBL4632333
 IC50 4.58 4.58 26540.0 1
GABA-A receptor; GABA-A site (alpha1/beta2 interface)
CHEMBL1907597
 EC50 4.57 4.57 27200.0 1
BV-2
CHEMBL614781
 IC50 4.28 4.28 52300.0 1
HUVEC
CHEMBL613979
 IC50 4.25 4.25 55800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cannabinoid receptor 2 Ki = 44.0 nM 7.36 Displacement of [3H]CP55,940 from recombinant human CB2 receptor expressed in CH... 24900561
Prostaglandin G/H synthase 2 IC50 = 60.0 nM 7.22 Inhibition of COX2 in sheep placental vesicle by enzyme immunoassay 19481465
Prostaglandin G/H synthase 1 IC50 = 100.0 nM 7.0 Inhibition of COX1 in ram seminal vesicle by enzyme immunoassay 19481465
A549 IC50 = 1240.0 nM 5.91 Cytotoxicity against human A549 cells after 72 hrs by MTS assay 22533983
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 1500.0 nM 5.82 Inhibition of 5LOX-mediated LTB4 formation in stimulated human polymorphonuclear... 19481465
A549 IC50 = 1560.0 nM 5.81 Cytotoxicity against human A549 cells after 24 hrs by MTS assay 22533983
NON-PROTEIN TARGET IC50 = 8180.0 nM 5.09 Antiinflammatory activity in human neutrophils assessed as inhibition of FMLP/CB... 26928286
HT-29 IC50 = 14130.0 nM 4.85 Cytotoxicity against human HT-29 cells after 72 hrs by MTS assay 22533983
NON-PROTEIN TARGET IC50 = 14320.0 nM 4.84 Antiinflammatory activity in human neutrophils assessed as inhibition of FMLP/CB... 26928286
A2780 IC50 = 14670.0 nM 4.83 Antiproliferative activity against human A2780 cells assessed as reduction in ce... 32996316
PANC-1 IC50 = 16730.0 nM 4.78 Antiproliferative activity against human PANC1 cells assessed as reduction in ce... 32996316
HepG2 IC50 = 17470.0 nM 4.76 Antiproliferative activity against human HepG2 cells assessed as reduction in ce... 32996316
RAW264.7 IC50 = 18000.0 nM 4.75 Inhibition of LPS-induced NO production in mouse RAW264.7 cells after 24 hrs by ... 22494844
PC-3 IC50 = 17870.0 nM 4.75 Antiproliferative activity against human PC-3 cells assessed as reduction in cel... 32996316
HT-29 IC50 = 21070.0 nM 4.68 Antiproliferative activity against human HT29 cells assessed as reduction in cel... 32996316
A549 IC50 = 21970.0 nM 4.66 Antiproliferative activity against human A549 cells assessed as reduction in cel... 32996316
HT-29 IC50 = 22450.0 nM 4.65 Cytotoxicity against human HT-29 cells after 24 hrs by MTS assay 22533983
UACC-903 IC50 = 24130.0 nM 4.62 Cytotoxicity against human UACC-903 cells after 72 hrs by MTS assay 22533983
L02 IC50 = 23940.0 nM 4.62 Antiproliferative activity against human L02 cells assessed as reduction in cell... 32996316
MCF7 IC50 = 24710.0 nM 4.61 Antiproliferative activity against human MCF7 cells assessed as growth inhibitio... 31831382

Literature References

PubMed DOI Target Context # Activities
22533983 10.1016/j.bmc.2012.03.062 HT-29 5
22533983 10.1016/j.bmc.2012.03.062 A549 5
22533983 10.1016/j.bmc.2012.03.062 UACC-903 5
21853991 10.1021/jm200830u HUVEC 4
26928286 10.1016/j.bmc.2016.01.049 NON-PROTEIN TARGET 4
21853991 10.1021/jm200830u Danio rerio 4
21699169 10.1021/jm200186n GABA-A receptor; GABA-A site (alpha1/beta2 interface) 3
19481465 10.1016/j.bmc.2009.05.018 Polyunsaturated fatty acid 5-lipoxygenase 2
19481465 10.1016/j.bmc.2009.05.018 Prostaglandin G/H synthase 2 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
19481465 10.1016/j.bmc.2009.05.018 Prostaglandin G/H synthase 1 2
30472026 10.1016/j.bmcl.2018.11.014 BV-2 2
21699169 10.1021/jm200186n No relevant target 1
21853991 10.1021/jm200830u A549 1
21853991 10.1021/jm200830u HepG2 1
32996316 10.1021/acs.jmedchem.0c00881 L02 1
17918910 10.1021/np070388c K562 1
17918910 10.1021/np070388c A549 1

Data from ChEMBL 36 via Core Engine