Compound Detail

CHEMBL128729

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COc1cc(/C=C/C(=O)/C=C/c2ccc(O)c(OC)c2)ccc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL128729
Phase	Preclinical
Structure Type	MOL
InChI Key	ISIMGBQRFXXNON-FCXRPNKRSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

326.4

MW (Da)

3.41

ALogP

HBA

HBD

76.0

PSA (Å²)

0.80

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	C19H18O5
MW	326.35
Aromatic Rings	2
Heavy Atoms	24
NP-Likeness	0.55

Activity Summary

IC50 56 meas. best 7.05

EC50 5 meas. best 6.08

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
UACC-62 CHEMBL614610	IC50	7.05	7.05	90.0	1
MCF7 CHEMBL387	IC50	6.92	5.73	120.0	3
11-beta-hydroxysteroid dehydrogenase 1 CHEMBL4235	IC50	6.59	5.37	257.0	2
11-beta-hydroxysteroid dehydrogenase 1 CHEMBL2391	IC50	6.54	5.665	292.0	2
HUVEC CHEMBL613979	IC50	6.4	6.4	400.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	6.22	6.22	600.0	1
Polyunsaturated fatty acid 5-lipoxygenase CHEMBL215	IC50	6.1	5.69	800.0	2
Trypanosoma brucei CHEMBL612849	EC50	6.08	6.08	840.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.08	5.278	830.0	5
Nuclear factor erythroid 2-related factor 2 CHEMBL1075094	EC50	6.05	5.525	900.0	2
Ca-Ski CHEMBL1075403	EC50	5.99	5.99	1030.0	1
HeLa CHEMBL399	EC50	5.99	5.99	1030.0	1
PC-3 CHEMBL390	IC50	5.9	5.5775	1250.0	4
LNCaP CHEMBL612518	IC50	5.85	5.4733	1400.0	3
NCI-H460 CHEMBL396	IC50	5.82	5.82	1530.0	1
Nuclear factor NF-kappa-B complex CHEMBL2094258	IC50	5.75	5.75	1800.0	1
K562 CHEMBL385	IC50	5.74	5.74	1840.0	1
OVCAR-3 CHEMBL614213	IC50	5.66	5.66	2200.0	1
HT-29 CHEMBL384	IC50	5.64	5.585	2300.0	2
MDA-MB-231 CHEMBL400	IC50	5.55	5.55	2800.0	1
Unchecked CHEMBL612545	IC50	5.48	5.354	3280.0	5
LS174T CHEMBL614097	IC50	5.43	5.43	3700.0	1
PANC-1 CHEMBL614139	IC50	5.33	5.33	4620.0	1
Signal transducer and activator of transcription 3 CHEMBL4026	IC50	5.22	5.22	6000.0	1
CNE CHEMBL613824	IC50	5.17	5.17	6800.0	2
GCIY CHEMBL2366234	IC50	5.13	5.13	7320.0	1
No relevant target CHEMBL2362975	IC50	5.03	4.51	9240.0	4
B16-F10 CHEMBL612656	IC50	4.67	4.67	21470.0	1
PBMC CHEMBL613107	IC50	4.46	4.46	34700.0	1
Human immunodeficiency virus type 1 integrase CHEMBL3471	IC50	4.43	4.43	37000.0	2
Cytochrome P450 1A2 CHEMBL3356	IC50	4.38	4.38	41500.0	1
ADMET CHEMBL612558	IC50	4.29	4.29	51810.0	1
L1210 CHEMBL386	IC50	4.25	4.25	56100.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	2964.0	ng.hr.mL-1	Rattus norvegicus
AUC	4913.0	ng.hr.mL-1	Rattus norvegicus
Cmax	2518.77	nM	Rattus norvegicus
MRT	2.959	hr	Rattus norvegicus
MRT	8.478	hr	Rattus norvegicus
T1/2	5.964	hr	Rattus norvegicus
Tmax	1.0	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
UACC-62	IC50	=	90.0	nM	7.05	Antitumor activity against human UACC62 cells after 48 hrs by SRB assay	20696583
MCF7	IC50	=	120.0	nM	6.92	Antitumor activity against human MCF7 cells after 48 hrs by SRB assay	20696583
11-beta-hydroxysteroid dehydrogenase 1	IC50	=	257.0	nM	6.59	Inhibition of human 11beta-HSD1 transfected in CHOP cells	23800686
11-beta-hydroxysteroid dehydrogenase 1	IC50	=	292.0	nM	6.54	Inhibition of 11beta-HSD1 in Sprague-Dawley rat leydig cells at 100 uM	23800686
HUVEC	IC50	=	400.0	nM	6.4	Anti-angiogenesis activity in HUVEC cells	32172081
Cytochrome P450 2D6	IC50	=	600.0	nM	6.22	Inhibition of human recombinant CYP2D6	18249473
Polyunsaturated fatty acid 5-lipoxygenase	IC50	=	800.0	nM	6.1	Inhibition of human recombinant 5-LO expressed in Escherichia coli Bl21 (DE3) us...	24920381
NON-PROTEIN TARGET	IC50	=	830.0	nM	6.08	Antitumor activity against human NCI/ADR cells after 48 hrs by SRB assay	20696583
Trypanosoma brucei	EC50	=	840.0	nM	6.08	Antitrypanosomal activity against Trypanosoma brucei Lister 427 assessed as para...	36608774
Nuclear factor erythroid 2-related factor 2	EC50	=	900.0	nM	6.05	Activation of Nrf2 transcriptional activity in human LNCaP cells after 6 hrs by ...	24920381
Ca-Ski	EC50	=	1030.0	nM	5.99	Antiproliferative activity against human Ca-Ski cells assessed as cell growth in...	32172081
HeLa	EC50	=	1030.0	nM	5.99	Antiproliferative activity against human HeLa cells assessed as cell growth inhi...	32172081
PC-3	IC50	=	1250.0	nM	5.9	Antitumor activity against human PC3 cells after 48 hrs by SRB assay	20696583
LNCaP	IC50	=	1400.0	nM	5.85	Cytotoxicity against human LNCaP cell line	16789753
NCI-H460	IC50	=	1530.0	nM	5.82	Antitumor activity against human NCI-H460 cells after 48 hrs by SRB assay	20696583
Nuclear factor NF-kappa-B complex	IC50	=	1800.0	nM	5.75	Inhibition of TNFalpha-induced NF-kappaB transcriptional activity in human 5.1 c...	24920381
K562	IC50	=	1840.0	nM	5.74	Antitumor activity against human K562 cells after 48 hrs by SRB assay	20696583
NON-PROTEIN TARGET	IC50	=	1990.0	nM	5.7	Antitumor activity against human 786-O cells after 48 hrs by SRB assay	20696583
OVCAR-3	IC50	=	2200.0	nM	5.66	Antitumor activity against human OVCAR-3 cells after 48 hrs by SRB assay	20696583
HT-29	IC50	=	2300.0	nM	5.64	Antitumor activity against human HT-29 cells after 48 hrs by SRB assay	20696583

Literature References

PubMed	DOI	Target Context	# Activities
26483137	10.1016/j.bmcl.2015.10.022	Staphylococcus aureus	16
27908756	10.1016/j.bmc.2016.11.023	No relevant target	10
19481942	10.1016/j.bmc.2009.05.034	Mus musculus	10
26483137	10.1016/j.bmcl.2015.10.022	ADMET	9
19243951	10.1016/j.bmc.2008.10.044	Plasma	9
19243951	10.1016/j.bmc.2008.10.044	Rattus norvegicus	8
23800686	10.1016/j.bmcl.2013.05.080	11-beta-hydroxysteroid dehydrogenase 1	5
31767266	10.1016/j.bmcl.2019.126760	Transcription factor p65	4
24275249	10.1016/j.ejmech.2013.10.073	Molecular identity unknown	4
23742639	10.1021/np400148e	Unchecked	4
25728027	10.1016/j.ejmech.2015.02.005	No relevant target	4
18249473	10.1016/j.ejmech.2007.10.034	Cytochrome P450 2D6	3
32172081	10.1016/j.ejmech.2020.112177	Unchecked	3
18249473	10.1016/j.ejmech.2007.10.034	Cytochrome P450 1A2	3
23800686	10.1016/j.bmcl.2013.05.080	11-beta-hydroxysteroid dehydrogenase type 2	2
23742639	10.1021/np400148e	Mitogen-activated protein kinase 8	2
23742639	10.1021/np400148e	Nuclear factor erythroid 2-related factor 2	2
24920381	10.1021/jm500308c	Prostaglandin G/H synthase 1	2
25728027	10.1016/j.ejmech.2015.02.005	NON-PROTEIN TARGET	2
24920381	10.1021/jm500308c	Polyunsaturated fatty acid 5-lipoxygenase	2

Data from ChEMBL 36 via Core Engine