Compound Detail

CHEMBL296411

TRISMETHOXYRESVERATROL

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COc1ccc(/C=C/c2cc(OC)cc(OC)c2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL296411
Name	TRISMETHOXYRESVERATROL
Phase	Preclinical
Structure Type	MOL
InChI Key	GDHNBPHYVRHYCC-SNAWJCMRSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

270.3

MW (Da)

3.88

ALogP

HBA

HBD

27.7

PSA (Å²)

0.77

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C17H18O3
MW	270.33
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	0.05

Activity Summary

IC50 43 meas. best 8.52

Ki 3 meas. best 8.11

EC50 2 meas. best 5.77

Kd 1 meas. best 5.39

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cytochrome P450 1A CHEMBL3544905	IC50	8.52	8.52	3.0	1
Aryl hydrocarbon receptor CHEMBL4725	Ki	8.11	8.11	7.7	1
Estrogen receptor CHEMBL206	Ki	6.58	6.58	261.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	6.12	5.78	760.0	2
Cytochrome P450 1B1 CHEMBL4878	IC50	6.1	6.1	790.0	1
Cytochrome P450 1A1 CHEMBL2231	IC50	6.08	6.08	830.0	1
HCT-116 CHEMBL394	IC50	5.96	5.6	1100.0	2
MCF7 CHEMBL387	IC50	5.96	5.52	1100.0	2
MDA-MB-231 CHEMBL400	IC50	5.92	5.92	1200.0	1
Prostaglandin G/H synthase 1 CHEMBL2949	IC50	5.91	5.91	1228.0	1
Prostaglandin G/H synthase 2 CHEMBL230	IC50	5.78	5.78	1667.0	1
Transient receptor potential cation channel subfamily A member 1 CHEMBL5160	EC50	5.77	5.77	1700.0	1
ADMET CHEMBL612558	IC50	5.68	5.68	2100.0	1
HL-60 CHEMBL383	IC50	5.6	5.6	2500.0	2
Unchecked CHEMBL612545	IC50	5.58	5.065	2600.0	2
Transient receptor potential cation channel subfamily A member 1 CHEMBL5160	IC50	5.52	5.52	3000.0	1
Transthyretin CHEMBL3194	Kd	5.39	5.39	4100.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.32	5.3	4830.0	2
Cytochrome P450 1A2 CHEMBL3356	IC50	5.21	5.21	6200.0	1
K562 CHEMBL385	IC50	5.19	5.19	6390.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	5.1	5.1	8000.0	1
Bcr/Abl fusion protein CHEMBL2096618	IC50	5.0	5.0	10000.0	1
KB CHEMBL398	IC50	4.99	4.87	10300.0	2
Caco-2 CHEMBL614058	IC50	4.92	4.92	11950.0	1
SK-MEL CHEMBL614914	IC50	4.91	4.91	12200.0	1
Ishikawa CHEMBL614649	IC50	4.9	4.9	12600.0	1
HeLa CHEMBL399	IC50	4.88	4.88	13300.0	1
Aromatase CHEMBL1978	IC50	4.87	4.87	13600.0	1
HT-29 CHEMBL384	IC50	4.85	4.8133	14000.0	3
Ribosyldihydronicotinamide dehydrogenase [quinone] CHEMBL3959	IC50	4.84	4.84	14600.0	1
BT-549 CHEMBL614072	IC50	4.81	4.81	15600.0	1
LLC-PK1 CHEMBL614577	IC50	4.7	4.7	20000.0	1
Mus musculus CHEMBL375	IC50	4.66	4.66	22000.0	1
Vero CHEMBL391	IC50	4.57	4.57	26700.0	1
MIA PaCa-2 CHEMBL614725	IC50	4.46	4.46	35000.0	1
SW480 CHEMBL612544	IC50	4.27	4.27	54000.0	1
SK-OV-3 CHEMBL614925	IC50	4.26	4.26	55500.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cytochrome P450 1A	IC50	=	3.0	nM	8.52	Inhibtion of CYP1A (unknown origin)	32485531
Aryl hydrocarbon receptor	Ki	=	7.7	nM	8.11	Binding affinity for aryl hydrocarbon receptor (AhR) of rabbit liver cytosol inc...	15634023
Estrogen receptor	Ki	=	261.0	nM	6.58	Binding affinity for estrogen receptor (ER) alpha of MCF-7 cell cytosol incubate...	15634023
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	760.0	nM	6.12	Inhibition of 5-LOX in human PMNL cells assessed as A23187-stimulated LTB4 produ...	31351395
Cytochrome P450 1B1	IC50	=	790.0	nM	6.1	Inhibition of ethoxyresorufin O-deethylation (EROD) in bicistronic bacterial mem...	11754588
Cytochrome P450 1A1	IC50	=	830.0	nM	6.08	Inhibition of ethoxyresorufin O-deethylation (EROD) in bicistronic bacterial mem...	11754588
MCF7	IC50	=	1100.0	nM	5.96	Cytotoxicity against human MCF7 cells after 24 hrs by MTT assay	21215623
HCT-116	IC50	=	1100.0	nM	5.96	Anticancer activity against human HCT-116 cells assessed as cell growth inhibiti...	32485531
MDA-MB-231	IC50	=	1200.0	nM	5.92	Inhibitory concentration required for antiproliferative activity against human M...	16250636
Prostaglandin G/H synthase 1	IC50	=	1228.0	nM	5.91	Inhibition of ovine COX-1 using arachidonic acid as substrate assessed as PGE2 p...	26850006
Prostaglandin G/H synthase 2	IC50	=	1667.0	nM	5.78	Inhibition of human recombinant COX-2 using arachidonic acid as substrate assess...	26850006
Transient receptor potential cation channel subfamily A member 1	EC50	=	1700.0	nM	5.77	Agonist activity at rat TRPA1 expressed in HEK293 cells assessed as induction of...	26750258
ADMET	IC50	=	2100.0	nM	5.68	Cytotoxicity against human IMR90 cells after 24 hrs by MTT assay	21215623
HL-60	IC50	=	2500.0	nM	5.6	Antiproliferative activity against human HL60 cells	16580204
HL-60	IC50	=	2500.0	nM	5.6	Antiproliferative activity against human HL60 cell line	16686543
Unchecked	IC50	=	2600.0	nM	5.58	Induction of NAD(P)H/quinone reductase activity (unknown origin)	32485531
Transient receptor potential cation channel subfamily A member 1	IC50	=	3000.0	nM	5.52	Antagonist activity at rat TRPA1 expressed in HEK293 cells assessed as inhibitio...	26750258
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	3620.0	nM	5.44	Inhibition of human 5-LOX expressed in Escherichia coli BL21 using arachidonic a...	31351395
Transthyretin	Kd	=	4100.0	nM	5.39	Binding affinity to recombinant N-terminal hexa-histidine tagged TTR V30M mutant...	37910439
NON-PROTEIN TARGET	IC50	=	4830.0	nM	5.32	Cytotoxicity against Homo sapiens (human) HCT28 cells assessed as growth inhibit...	-

Literature References

PubMed	DOI	Target Context	# Activities
20627379	10.1016/j.ejmech.2010.05.019	HT-29	9
26850006	10.1016/j.bmcl.2016.01.069	Mus musculus	6
23547843	10.1021/np300893n	Molecular identity unknown	6
35621995	10.1021/acs.jnatprod.1c01107	Enterococcus faecalis	5
16580204	10.1016/j.bmcl.2006.03.028	HL-60	4
21880495	10.1016/j.bmc.2011.08.008	Protein kinase C alpha type	4
20395019	10.1016/j.ejmech.2010.03.024	SW480	4
37910439	10.1021/acs.jmedchem.3c01698	Transthyretin	4
27426305	10.1016/j.bmcl.2016.07.018	ADMET	4
27426305	10.1016/j.bmcl.2016.07.018	Thymocyte	4
16686543	10.1021/jm060253o	HL-60	3
26750258	10.1016/j.bmcl.2015.12.065	Transient receptor potential cation channel subfamily A member 1	3
35621995	10.1021/acs.jnatprod.1c01107	Staphylococcus aureus	3
23547843	10.1021/np300893n	HeLa	2
21215623	10.1016/j.bmcl.2010.12.029	ADMET	2
37910439	10.1021/acs.jmedchem.3c01698	No relevant target	2
26850006	10.1016/j.bmcl.2016.01.069	HepG2	2
22088309	10.1016/j.bmc.2011.10.066	NON-PROTEIN TARGET	2
19640715	10.1016/j.bmcl.2009.07.082	Unchecked	2
21215623	10.1016/j.bmcl.2010.12.029	MCF7	2

Data from ChEMBL 36 via Core Engine