Compound Detail

CHEMBL431701

SILYBIN A

🧪 Phase III

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🧪 Phase III

COc1cc([C@H]2Oc3cc([C@H]4Oc5cc(O)cc(O)c5C(=O)[C@@H]4O)ccc3O[C@@H]2CO)ccc1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL431701
Name	SILYBIN A
Phase	Phase III
Structure Type	MOL
InChI Key	SEBFKMXJBCUCAI-HKTJVKLFSA-N

Known Names

NSC-651520 Silibinin a Silybin a Silymarin i

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	Single Enantiomer

Flags

Natural Product

Extended Properties

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

Indications

Atrial Fibrillation Depressive Disorder Hepatitis C Proteinuria Diabetes Mellitus, Type 2 Hepatitis A Hepatitis C, Chronic Hepatitis E Hepatitis, Viral, Human Melanosis Neoplasms Non-alcoholic Fatty Liver Disease Carcinoma, Hepatocellular Immune System Diseases

Activity Summary

IC50 23 meas. best 5.57

EC50 2 meas. best 4.12

Kd 1 meas.

Ki 1 meas. best 4.22

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Solute carrier organic anion transporter family member 1B3 CHEMBL1743121	IC50	5.57	5.57	2700.0	1
Solute carrier organic anion transporter family member 2B1 CHEMBL1743124	IC50	5.35	5.35	4500.0	1
HUVEC CHEMBL613979	IC50	5.05	4.63	8830.0	2
Solute carrier organic anion transporter family member 1B1 CHEMBL1697668	IC50	5.01	5.01	9700.0	1
Molecular identity unknown CHEMBL612546	IC50	4.92	4.92	12000.0	1
Cytochrome P450 2C9 CHEMBL3397	IC50	4.75	4.75	18000.0	1
dengue virus type 3 CHEMBL612717	IC50	4.73	4.73	18480.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.7	4.275	20000.0	4
Unchecked CHEMBL612545	IC50	4.68	4.35	21000.0	3
Hepatocyte CHEMBL3140324	IC50	4.52	4.4667	29900.0	3
Hepatitis C virus CHEMBL379	IC50	4.3	4.3	50000.0	1
Solute carrier family 2, facilitated glucose transporter member 4 CHEMBL1250410	Ki	4.22	4.22	60000.0	1
HepG2 CHEMBL395	EC50	4.12	4.12	75700.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Cmax	1202.22	nM	Homo sapiens
Cmax	82.91	nM	Homo sapiens
Cmax	80.0	nM	Homo sapiens
F	0.5	%	Homo sapiens
Fu	0.05	-	Homo sapiens
T1/2	2.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Solute carrier organic anion transporter family member 1B3	IC50	=	2700.0	nM	5.57	Inhibition of OATP1B3 (unknown origin) expressed in HEK293 cells assessed as red...	23401473
Solute carrier organic anion transporter family member 2B1	IC50	=	4500.0	nM	5.35	Inhibition of OATP2B1 (unknown origin) expressed in MDCK2 cells assessed as redu...	23401473
HUVEC	IC50	=	8830.0	nM	5.05	Antiproliferative activity against HUVEC assessed as inhibition of cell growth a...	21928794
Solute carrier organic anion transporter family member 1B1	IC50	=	9700.0	nM	5.01	Inhibition of OATP1B1 (unknown origin) expressed in HEK293 cells assessed as red...	23401473
Molecular identity unknown	IC50	=	12000.0	nM	4.92	Downregulation of telomerase expression in human T47D cells after 72 hrs in pres...	27517806
Cytochrome P450 2C9	IC50	=	18000.0	nM	4.75	Inhibition of CYP2C9 in human liver microsomes using (S)-warfarin as substrate a...	27517806
dengue virus type 3	IC50	=	18480.0	nM	4.73	Antiviral activity against DENV3 H87 assessed as reduction in viral RNA copy num...	36167010
NON-PROTEIN TARGET	IC50	=	20000.0	nM	4.7	Cytotoxicity against human T47D cells assessed as reduction in cell viability af...	27517806
Unchecked	IC50	=	21000.0	nM	4.68	Inhibition of theophylline-stimulated melanogenesis in mouse B16-4A5 cells after...	20189399
Hepatocyte	IC50	=	29900.0	nM	4.52	Hepatoprotective activity against D-GaIN/TNFalpha-induced cell death in mouse he...	29353722
Hepatocyte	IC50	=	33600.0	nM	4.47	Hepatoprotective activity against D-GaIN/TNFalpha-induced cell death in mouse he...	29353722
Hepatocyte	IC50	=	38800.0	nM	4.41	Hepatoprotective activity against D-GaIN-induced toxicity in mouse hepatocyte re...	29353722
NON-PROTEIN TARGET	IC50	=	50000.0	nM	4.3	Cytotoxicity against human LoVo cells assessed as reduction in cell growth after...	27517806
Hepatitis C virus	IC50	=	50000.0	nM	4.3	Antiviral activity against HCV JFH-1 infected in human Huh7.5.1 cells assessed a...	30485098
Unchecked	IC50	=	51500.0	nM	4.29	Inhibition of collagen type 1 deposition in human LX2 cells	33775837
Solute carrier family 2, facilitated glucose transporter member 4	Ki	=	60000.0	nM	4.22	Competitive inhibition of GLUT4 in mouse 3T3L1 cells assessed as reduction in in...	28042452
HUVEC	IC50	=	62330.0	nM	4.21	Cytotoxicity against HUVEC assessed as cell viability after 16 hrs by MTT assay	21928794
HepG2	EC50	=	75700.0	nM	4.12	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability b...	29353722
NON-PROTEIN TARGET	IC50	=	80000.0	nM	4.1	Cytotoxicity against human Huh7.5.1 cells after 72 hrs	23673225
Unchecked	IC50	=	83700.0	nM	4.08	Inhibition of laminin deposition in human LX2 cells	33775837

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1016/S0960-894X(97)10155-X	Rattus norvegicus	30
20189399	10.1016/j.bmc.2010.01.046	Unchecked	17
27517806	10.1016/j.ejmech.2016.07.070	NON-PROTEIN TARGET	14
23401473	10.1124/dmd.112.048272	Unchecked	6
20189399	10.1016/j.bmc.2010.01.046	Tyrosinase	6
23401473	10.1124/dmd.112.048272	ADMET	6
35576657	10.1016/j.bmc.2022.116813	Unchecked	5
29353722	10.1016/j.ejmech.2018.01.011	Hepatocyte	5
20189399	10.1016/j.bmc.2010.01.046	ADMET	5
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
33775837	10.1016/j.bmcl.2021.127994	Unchecked	4
21928794	10.1021/jm201034h	HUVEC	3
23401473	10.1124/dmd.112.048272	Solute carrier organic anion transporter family member 1B1	3
23401473	10.1124/dmd.112.048272	Solute carrier organic anion transporter family member 1B3	3
23401473	10.1124/dmd.112.048272	Solute carrier organic anion transporter family member 2B1	3
23401473	10.1124/dmd.112.048272	Homo sapiens	3
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
23401473	10.1124/dmd.112.048272	Plasma	2

Data from ChEMBL 36 via Core Engine