Compound Detail

CHEMBL12089

BERBERINE CHLORIDE

Phase I

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Phase I

COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2.[Cl-]

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL12089
Name	BERBERINE CHLORIDE
Phase	Phase I
Structure Type	MOL
InChI Key	VKJGBAJNNALVAV-UHFFFAOYSA-M
Parent Compound	CHEMBL295124
Active Moiety	CHEMBL295124

Known Names

Berberine chloride Berberine hydrochloride Berberinum GNF-Pf-4545 NSC-163088 NSC-646666

Targets

112

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

336.4

MW (Da)

3.10

ALogP

HBA

HBD

40.8

PSA (Å²)

0.67

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C20H18ClNO4
MW	371.82
Aromatic Rings	3
Heavy Atoms	25
NP-Likeness	1.30

Indications

Colitis, Ulcerative Diabetes Mellitus

Activity Summary

IC50 90 meas. best 7.4

Ki 14 meas. best 7.23

EC50 5 meas. best 6.89

Kd 3 meas. best 7.64

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cell division protein FtsZ CHEMBL3999	Kd	7.64	7.64	23.0	1
Acetylcholinesterase CHEMBL220	IC50	7.4	6.12	40.0	4
Unchecked CHEMBL612545	Ki	7.23	6.35	59.0	3
Unchecked CHEMBL612545	IC50	7.02	5.2067	95.0	9
Human immunodeficiency virus 1 CHEMBL378	EC50	6.89	6.89	130.0	1
Plasmodium falciparum CHEMBL364	EC50	6.66	6.51	218.0	2
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.56	6.56	274.0	1
Acetylcholinesterase CHEMBL4078	Ki	6.54	6.54	289.0	1
Acetylcholinesterase CHEMBL4078	IC50	6.43	6.3057	374.0	7
5-hydroxytryptamine receptor 4 CHEMBL5017	Ki	6.43	6.43	370.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.38	6.38	412.0	1
Unchecked CHEMBL612545	EC50	6.36	6.36	433.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.27	6.27	542.0	1
Plasmodium yoelii CHEMBL612889	IC50	6.26	6.26	548.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	6.22	6.22	601.0	1
Human betaherpesvirus 5 CHEMBL371	IC50	6.17	6.17	680.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	Ki	6.13	6.13	742.0	1
Plasmodium falciparum CHEMBL364	IC50	6.01	6.01	968.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	5.89	5.89	1289.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	5.66	5.66	2187.0	1
5-hydroxytryptamine receptor 4 CHEMBL5017	IC50	5.65	5.65	2222.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	5.55	5.55	2837.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.51	5.51	3100.0	1
Muscarinic acetylcholine receptor M1 CHEMBL216	IC50	5.51	5.51	3080.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	5.46	5.46	3437.0	1
Serine/threonine-protein kinase Nek7 CHEMBL4849	IC50	5.38	5.38	4200.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	5.35	5.35	4504.2	1
HL-60 CHEMBL383	IC50	5.23	4.895	5830.0	2
KB CHEMBL398	IC50	5.22	5.175	6030.0	2
A549 CHEMBL392	IC50	5.2	5.2	6270.0	1
BGC-823 CHEMBL614526	IC50	5.15	5.15	7040.0	1
HepG2 CHEMBL395	IC50	5.08	4.78	8320.0	3
HT-29 CHEMBL384	IC50	5.07	5.07	8450.0	1
Histone acetyltransferase p300 CHEMBL3784	IC50	5.05	5.05	8910.0	1
Cholinesterase CHEMBL5763	Ki	5.04	5.04	9200.0	1
Cell division protein FtsZ CHEMBL3999	IC50	5.0	4.9	10000.0	2
SK-MEL-2 CHEMBL614917	IC50	4.86	4.86	13760.0	1
PC-3 CHEMBL390	IC50	4.84	4.67	14390.0	2
Serine/threonine-protein kinase Nek7 CHEMBL4849	Kd	4.81	4.81	15600.0	1
D(1A) dopamine receptor CHEMBL2056	IC50	4.81	4.81	15500.0	1
Bel-7402 CHEMBL614279	IC50	4.79	4.79	16280.0	1
SK-OV-3 CHEMBL614925	IC50	4.78	4.78	16440.0	1
HCT-15 CHEMBL612263	IC50	4.78	4.78	16590.0	1
D(2) dopamine receptor CHEMBL217	IC50	4.77	4.59	17100.0	2
Cholinesterase CHEMBL5763	IC50	4.74	4.74	18200.0	3
Butyrylcholinesterase CHEMBL5077	IC50	4.74	4.74	18200.0	3
Cholinesterase CHEMBL1914	IC50	4.72	4.525	18970.0	2
MDA-MB-231 CHEMBL400	IC50	4.69	4.69	20600.0	1
Retinoic acid receptor RXR-alpha CHEMBL2061	Kd	4.61	4.61	24800.0	1
SW-620 CHEMBL612262	IC50	4.6	4.6	25000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	99.0	ng.hr.mL-1	Rattus norvegicus
Cmax	0.07	nM	Homo sapiens
Cmax	0.14	nM	Homo sapiens
Cmax	0.13	nM	Homo sapiens
Cmax	1.4	nM	Homo sapiens
Cmax	4.0	nM	Homo sapiens
Cmax	6.7	nM	Homo sapiens
Cmax	1.7	nM	Homo sapiens
Cmax	5.6	nM	Homo sapiens
Cmax	8.601	nM	Rattus norvegicus
F	1.0	%	Rattus norvegicus
F	0.544	%	Rattus norvegicus
Ka	12400.0	-	-
Ka	29300.0	-	-
Ka	1.28	10'-5/M	Bos taurus
MRT	31.51	hr	Rattus norvegicus
T1/2	2.94	hr	Homo sapiens
T1/2	28.98	hr	Rattus norvegicus
Tmax	1.0	hr	Homo sapiens
Tmax	1.0	hr	Homo sapiens
Tmax	2.0	hr	Homo sapiens
Tmax	2.0	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cell division protein FtsZ	Kd	=	23.0	nM	7.64	Displacement of bis-ANS from Escherichia coli FtsZ	26756351
Acetylcholinesterase	IC50	=	40.0	nM	7.4	Inhibition of AChE assessed as hydrolysis of acetylcholine preincubated for 15 m...	21924611
Unchecked	Ki	=	59.0	nM	7.23	DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil)	-
Unchecked	IC50	=	95.0	nM	7.02	DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil)	-
Human immunodeficiency virus 1	EC50	=	130.0	nM	6.89	Antiviral activity against 0.05 MOI Human immunodeficiency virus 1 NL4.3 infecte...	21295891
Plasmodium falciparum	EC50	=	218.0	nM	6.66	NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati...	18579783
Alpha-2B adrenergic receptor	Ki	=	274.0	nM	6.56	DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin...	-
Acetylcholinesterase	Ki	=	289.0	nM	6.54	Inhibition of electric eel AChE by enzyme kinetics assay	20056426
Acetylcholinesterase	IC50	=	374.0	nM	6.43	Inhibition of electric eel AChE using acetylcholine chloride as substrate preinc...	22041172
Acetylcholinesterase	IC50	=	374.0	nM	6.43	Inhibition of electric eel AChE by modified Ellman method	20056426
5-hydroxytryptamine receptor 4	Ki	=	370.0	nM	6.43	DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT4 radioligand binding (ligand: [...	-
Acetylcholinesterase	IC50	=	374.0	nM	6.43	Inhibition of electric eel AChE using acetylthiocholine chloride as substrate pr...	23932451
Acetylcholinesterase	IC50	=	374.0	nM	6.43	Inhibition of electric eel Acetylcholinesterase	21397508
Acetylcholinesterase	IC50	=	374.0	nM	6.43	Inhibition of electric eel AChE after 15 mins by Ellman's method using acetylcho...	20880702
Acetylcholinesterase	IC50	=	374.0	nM	6.43	Inhibition of electric eel AChE by Ellman's assay	20471843
Alpha-2C adrenergic receptor	Ki	=	412.0	nM	6.38	DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912)	-
Plasmodium falciparum	EC50	=	442.0	nM	6.36	NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ...	18579783
Unchecked	EC50	=	433.0	nM	6.36	PubChem BioAssay. Leishmania major promastigote EC50 determinations. (Class of...	-
Sigma non-opioid intracellular receptor 1	Ki	=	542.0	nM	6.27	DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol)	-
Plasmodium yoelii	IC50	=	548.0	nM	6.26	NOVARTIS: Antimalarial liver stage activity measured as reduction in Plasmodium ...	22096101

Literature References

PubMed	DOI	Target Context	# Activities
32391701	10.1021/acs.jmedchem.0c00088	Retinoic acid receptor RXR-alpha	46
32432470	10.1021/acs.jnatprod.0c00175	Mus musculus	25
33440945	10.1021/acs.jmedchem.0c01743	Unchecked	24
33069077	10.1016/j.bmc.2020.115697	Mus musculus	18
32391701	10.1021/acs.jmedchem.0c00088	ADMET	16
23182088	10.1016/j.bmcl.2012.10.098	HepG2	15
24593257	10.1021/np400607k	No relevant target	14
-	10.1007/s00044-013-0844-5	Staphylococcus aureus	14
24593257	10.1021/np400607k	Homo sapiens	11
25740159	10.1016/j.bmcl.2015.02.013	No relevant target	9
20498327	10.1128/aac.01715-09	Quinolone resistance protein NorA	7
22459209	10.1016/j.bmc.2012.03.006	Nucleic Acid	7
29545016	10.1016/j.bmc.2018.02.052	Unchecked	7
32828421	10.1016/j.bmc.2020.115644	NAD(+) hydrolase SARM1	6
19090767	10.1021/jm801157z	Rattus norvegicus	6
-	10.1016/S0960-894X(96)00429-5	Acetylcholine receptor subunit delta	6
32432470	10.1021/acs.jnatprod.0c00175	ADMET	5
20498327	10.1128/aac.01715-09	Staphylococcus aureus	5
24593257	10.1021/np400607k	Plasma	5
17574421	10.1016/j.bmc.2007.05.050	Unchecked	5

Data from ChEMBL 36 via Core Engine