Compound Detail

CHEMBL9509

SILIBININ

🧪 Phase III

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🧪 Phase III

COc1cc(C2Oc3cc([C@H]4Oc5cc(O)cc(O)c5C(=O)[C@@H]4O)ccc3OC2CO)ccc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL9509
Name	SILIBININ
Phase	Phase III
Structure Type	MOL
InChI Key	SEBFKMXJBCUCAI-DBMPWETRSA-N

Known Names

Legalon Silibin Silibinin Silibinin a-silibinin b mixt. Silibinina Silibinine Silliver Silybin Silybine Silymarin

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

482.4

MW (Da)

2.36

ALogP

HBA

HBD

155.1

PSA (Å²)

0.37

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Racemic

Flags

Natural Product

Extended Properties

Molecular Formula	C25H22O10
MW	482.44
Aromatic Rings	3
Heavy Atoms	35
NP-Likeness	1.96

Indications

Hepatitis C Liver Failure Prostatic Neoplasms, Castration-Resistant Tobacco Use Disorder

ATC Classification

A05BA03

silymarin

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: BILE AND LIVER THERAPY

Activity Summary

IC50 45 meas. best 5.77

Ki 9 meas. best 6.16

EC50 5 meas. best 4.72

Kd 2 meas. best 5.17

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosinase CHEMBL3318	Ki	6.16	5.6175	700.0	4
Tyrosinase CHEMBL3318	IC50	5.77	5.345	1700.0	2
No relevant target CHEMBL2362975	IC50	5.53	5.53	2940.0	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	Ki	5.49	5.49	3270.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	Ki	5.47	5.47	3370.0	1
Trypsin CHEMBL2095204	IC50	5.43	5.43	3700.0	1
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	5.37	5.37	4265.8	1
Cytochrome P450 2C9 CHEMBL3397	Ki	5.3	5.3	5000.0	1
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	IC50	5.21	5.21	6165.9	1
ATP-dependent translocase ABCB1 CHEMBL2573	Kd	5.17	5.17	6800.0	1
HUVEC CHEMBL613979	IC50	5.0	4.57	9990.0	2
Hepatocyte CHEMBL3140324	IC50	4.82	4.444	15000.0	5
Prothrombin CHEMBL204	Kd	4.73	4.73	18600.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	4.72	4.72	18830.0	1
Prothrombin CHEMBL204	IC50	4.68	4.64	20900.0	2
Urokinase-type plasminogen activator CHEMBL3286	IC50	4.68	4.68	21000.0	1
Chikungunya virus CHEMBL4296563	IC50	4.65	4.65	22500.0	1
Liver CHEMBL613642	IC50	4.64	4.248	22700.0	5
Cytochrome P450 3A4 CHEMBL340	Ki	4.5	4.5	32000.0	1
LNCaP CHEMBL612518	IC50	4.37	4.3667	43030.0	3
HepG2 CHEMBL395	EC50	4.35	4.235	45000.0	2
HCT-116 CHEMBL394	IC50	4.3	4.3	50000.0	1
SW480 CHEMBL612544	IC50	4.3	4.3	50000.0	1
Liver microsomes CHEMBL613694	IC50	4.24	4.24	58100.0	1
Hepatitis C virus CHEMBL379	IC50	4.22	4.22	60000.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.16	4.1	69200.0	5
PC-3 CHEMBL390	IC50	4.14	4.14	72650.0	1
Xanthine dehydrogenase/oxidase CHEMBL1075246	IC50	4.09	4.09	80300.0	1
DU-145 CHEMBL613508	IC50	4.03	4.03	93340.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
KA	6.157	10'6L/mol	Agaricus bisporus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosinase	Ki	=	700.0	nM	6.16	Mixed type inhibition of monophenolase activity of mushroom tyrosinase assessed ...	30871862
Tyrosinase	Ki	=	700.0	nM	6.16	Inhibition of monophenolase activity of mushroom tyrosinase assessed as inhibiti...	30871862
Tyrosinase	IC50	=	1700.0	nM	5.77	Inhibition of monophenolase activity of mushroom tyrosinase assessed as reductio...	30871862
No relevant target	IC50	=	2940.0	nM	5.53	Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins ...	28068598
Solute carrier organic anion transporter family member 1B3	Ki	=	3270.0	nM	5.49	Ki values for sodium fluorescein (10 uM) uptake in OATP1B3-transfected CHO cells	23571415
Solute carrier organic anion transporter family member 1B1	Ki	=	3370.0	nM	5.47	Ki values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO cells	23571415
Trypsin	IC50	=	3700.0	nM	5.43	Inhibition of trypsin amidolytic activity (unknown origin)	24610996
Solute carrier organic anion transporter family member 1B3	IC50	=	4265.8	nM	5.37	pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B3-transfected CHO ce...	23571415
Cytochrome P450 2C9	Ki	=	5000.0	nM	5.3	Mechanism based inhibition of human cytochrome P450 2C9 measured by 7-EFC O-deet...	16248836
Solute carrier organic anion transporter family member 1B1	IC50	=	6165.95	nM	5.21	pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO ce...	23571415
ATP-dependent translocase ABCB1	Kd	=	6800.0	nM	5.17	Compound was tested for the binding affinity towards recombinant NBD2 C-terminal...	10673101
Tyrosinase	Ki	=	8400.0	nM	5.08	Inhibition of diphenolase activity of mushroom tyrosinase assessed as inhibition...	30871862
Tyrosinase	Ki	=	8500.0	nM	5.07	Mixed type inhibition of diphenolase activity of mushroom tyrosinase assessed as...	30871862
HUVEC	IC50	=	9990.0	nM	5.0	Antiproliferative activity against HUVEC assessed as inhibition of cell growth a...	21928794
Tyrosinase	IC50	=	12100.0	nM	4.92	Inhibition of diphenolase activity of mushroom tyrosinase assessed as reduction ...	30871862
Hepatocyte	IC50	=	15000.0	nM	4.82	Hepatoprotective activity in ddY mouse hepatocytes assessed as inhibition of D-g...	19775895
Prothrombin	Kd	=	18600.0	nM	4.73	Inhibition of human thrombin assessed as equilibrium dissociation constant at 50...	24610996
NON-PROTEIN TARGET	EC50	=	18830.0	nM	4.72	Antiproliferative activity against serum-stimulated rat HSC-T6 cells after 24 hr...	21459003
Prothrombin	IC50	=	20900.0	nM	4.68	Inhibition of thrombin (unknown origin) assessed as hydrolysis of N-benzoyl-phen...	24610996
Urokinase-type plasminogen activator	IC50	=	21000.0	nM	4.68	Inhibition of urokinase amidolytic activity (unknown origin)	24610996

Literature References

PubMed	DOI	Target Context	# Activities
19388706	10.1021/np8007123	Xanthine dehydrogenase/oxidase	21
24610996	10.1007/s00044-013-0829-4	Prothrombin	15
30871862	10.1016/j.bmc.2019.03.013	Tyrosinase	12
11325227	10.1021/np000393f	Hepatocyte	10
19775895	10.1016/j.bmc.2009.08.050	Hepatocyte	9
28068598	10.1016/j.ejmech.2016.12.051	No relevant target	7
11277757	10.1021/np000486x	Hepatocyte	7
29407994	10.1016/j.ejmech.2018.01.036	HT-22	6
22624880	10.1021/jm300246n	Rattus norvegicus	6
21928794	10.1021/jm201034h	HUVEC	6
6677713	10.1021/np50030a003	Hepatocyte	6
15104485	10.1021/np030368k	Hepatocyte	5
20159656	10.1016/j.bmc.2010.01.047	Hepatocyte	5
20159656	10.1016/j.bmc.2010.01.047	L929	5
22624880	10.1021/jm300246n	HT-22	5
27765508	10.1016/j.bmcl.2016.10.012	NON-PROTEIN TARGET	5
21459003	10.1016/j.bmc.2011.01.037	HepG2	4
21737270	10.1016/j.bmcl.2011.06.049	Rat1	4
21273068	10.1016/j.bmcl.2010.12.088	Heat shock protein HSP90	4
10785422	10.1021/np990581+	Hepatocyte	4

Data from ChEMBL 36 via Core Engine