Compound Detail

CHEMBL16171

WOGONIN

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

COc1c(O)cc(O)c2c(=O)cc(-c3ccccc3)oc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL16171
Name	WOGONIN
Phase	Preclinical
Structure Type	MOL
InChI Key	XLTFNNCXVBYBSX-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

284.3

MW (Da)

2.88

ALogP

HBA

HBD

79.9

PSA (Å²)

0.76

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	C16H12O5
MW	284.27
Aromatic Rings	3
Heavy Atoms	21
NP-Likeness	1.40

Activity Summary

IC50 42 meas. best 7.52

Ki 2 meas. best 5.69

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MCF7 CHEMBL387	IC50	7.52	5.025	30.0	6
CDK9/cyclin T1 CHEMBL2111389	IC50	6.72	6.7133	190.0	3
Cyclin-dependent kinase 9 CHEMBL3116	IC50	6.72	6.72	190.0	2
RAW264.7 CHEMBL612557	IC50	5.97	5.97	1080.0	1
Prostaglandin G/H synthase 2 CHEMBL4321	IC50	5.97	5.97	1070.0	1
Cyclin-dependent kinase 2 CHEMBL301	IC50	5.84	5.84	1460.0	1
CDK2/Cyclin A2 CHEMBL3038469	IC50	5.84	5.84	1460.0	1
Pyruvate kinase PKM CHEMBL1075189	IC50	5.7	5.7	2010.0	1
GABA-A receptor; anion channel CHEMBL2093872	Ki	5.69	5.69	2041.7	1
Pyruvate kinase PKM CHEMBL1075189	Ki	5.45	5.45	3530.0	1
CDK8/Cyclin C CHEMBL3038474	IC50	5.23	5.23	5900.0	1
Nitric oxide synthase, inducible CHEMBL3464	IC50	5.11	5.11	7800.0	1
Lysine-specific histone demethylase 1A CHEMBL6136	IC50	5.05	5.05	8870.0	1
CDK7/Cyclin H/MNAT1 CHEMBL3038473	IC50	4.91	4.91	12300.0	1
A549 CHEMBL392	IC50	4.8	4.6233	15800.0	3
Unchecked CHEMBL612545	IC50	4.78	4.78	16500.0	1
HepG2 CHEMBL395	IC50	4.75	4.664	17600.0	5
B16 CHEMBL381	IC50	4.58	4.58	26400.0	1
HCT-116 CHEMBL394	IC50	4.56	4.56	27300.0	1
HEK293 CHEMBL614818	IC50	4.55	4.55	28100.0	1
MV4-11 CHEMBL613835	IC50	4.51	4.51	30700.0	1
SW480 CHEMBL612544	IC50	4.46	4.46	35060.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.43	4.43	36870.0	1
SW1353 CHEMBL614944	IC50	4.41	4.41	39000.0	1
HT-29 CHEMBL384	IC50	4.4	4.4	39550.0	1
Prostaglandin G/H synthase 2 CHEMBL230	IC50	4.34	4.34	46000.0	3

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	11.3	mL.min-1.g-1	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MCF7	IC50	=	30.0	nM	7.52	Antiproliferative activity against human MCF7 cells incubated for 72 hrs by MTT ...	36205223
CDK9/cyclin T1	IC50	=	190.0	nM	6.72	Inhibition of human recombinant N-terminal GST-tagged CDK9 (2 to 372 residues)/N...	31238183
CDK9/cyclin T1	IC50	=	190.0	nM	6.72	Inhibition of human recombinant N-terminal GST-tagged CDK9 (2 to 372 residues) e...	30733087
Cyclin-dependent kinase 9	IC50	=	190.0	nM	6.72	Inhibition of CDK9 (unknown origin) using [33-p]-ATP as substrate incubated for ...	36205223
Cyclin-dependent kinase 9	IC50	=	190.0	nM	6.72	Inhibition of CDK9 (unknown origin)	35814933
CDK9/cyclin T1	IC50	=	198.0	nM	6.7	Inhibition of human CDK9/cyclin-T1 using YSPTSPSYSPTSPSYSPTSPKKK peptide as subs...	31238183
RAW264.7	IC50	=	1080.0	nM	5.97	Evaluated for inhibition of COX-2 catalyzed PGE-2 production from LPS induced RA...	14980657
Prostaglandin G/H synthase 2	IC50	=	1070.0	nM	5.97	Inhibition of COX2-mediated PGE2 production in LPS-stimulated mouse RAW264.7 cel...	19233646
CDK2/Cyclin A2	IC50	=	1460.0	nM	5.84	Inhibition of human CDK2/cyclin-A2 using H1 histone as substrate after 2 hrs by ...	31238183
Cyclin-dependent kinase 2	IC50	=	1460.0	nM	5.84	Inhibition of CDK2 (unknown origin)	30733087
Pyruvate kinase PKM	IC50	=	2010.0	nM	5.7	Inhibition of PKM2 (unknown origin) Ser205, Lys207, Hie78, Lys367, Asn75, Ile51,...	34726055
GABA-A receptor; anion channel	Ki	=	2041.74	nM	5.69	Binding affinity towards benzodiazepine site in GABAA receptor	11384234
Pyruvate kinase PKM	Ki	=	3530.0	nM	5.45	Binding affinity to PKM2 (unknown origin) assessed as oxidation of beta-NADH by ...	34726055
CDK8/Cyclin C	IC50	=	5900.0	nM	5.23	Inhibition of recombinant full length His tagged human CDK8/Cyclin C expressed i...	35536548
Nitric oxide synthase, inducible	IC50	=	7800.0	nM	5.11	Inhibition of iNOS-induced NO production in LPS-stimulated mouse BV2 cells after...	22366656
Lysine-specific histone demethylase 1A	IC50	=	8870.0	nM	5.05	Inhibition of LSD1 (unknown origin)	30552007
CDK7/Cyclin H/MNAT1	IC50	=	12300.0	nM	4.91	Inhibition of recombinant human full length C-terminal His6-tagged and N-termina...	30733087
A549	IC50	=	15800.0	nM	4.8	Cytotoxicity against human A549 cells assessed as reduction in cell viability af...	28117202
Unchecked	IC50	=	16500.0	nM	4.78	Cytotoxicity against human BCG823 cells assessed as reduction in cell viability ...	28117202
HepG2	IC50	=	17600.0	nM	4.75	Antiproliferative activity against human HepG2 cells assessed as reduction in ce...	31238183

Literature References

PubMed	DOI	Target Context	# Activities
21493073	10.1016/j.bmc.2011.03.040	3T3-L1	4
32088124	10.1016/j.bmc.2020.115372	Histone-lysine N-methyltransferase SETD7	3
31238183	10.1016/j.ejmech.2019.06.024	No relevant target	3
31238183	10.1016/j.ejmech.2019.06.024	CDK9/cyclin T1	3
31238183	10.1016/j.ejmech.2019.06.024	CDK2/Cyclin A2	2
19555121	10.1021/np900068t	SW1353	2
3379415	10.1021/np50056a030	Xanthine dehydrogenase/oxidase	2
34726055	10.1021/acs.jmedchem.1c00981	Pyruvate kinase PKM	2
19233646	10.1016/j.bmcl.2009.02.001	Prostaglandin G/H synthase 2	2
9214730	10.1021/np970035l	Trypsin	2
24549242	10.1016/j.ejmech.2014.01.046	Hepatitis B virus	2
28117202	10.1016/j.bmcl.2016.12.076	HepG2	2
19555121	10.1021/np900068t	HL-60	2
22137340	10.1016/j.bmcl.2011.11.041	Estrogen receptor	2
22366656	10.1016/j.bmcl.2012.01.135	Nitric oxide synthase, inducible	2
12713409	10.1021/np0205102	5-hydroxytryptamine receptor 7	1
37229829	10.1016/j.ejmech.2023.115447	MCF7	1
19555121	10.1021/np900068t	ADMET	1
19555121	10.1021/np900068t	Vero	1
14980657	10.1016/j.bmcl.2003.12.087	RAW264.7	1

Data from ChEMBL 36 via Core Engine