Compound Detail

CHEMBL504323

BERBAMINE

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COc1cc2c3cc1Oc1c(OC)c(OC)cc4c1[C@@H](Cc1ccc(O)c(c1)Oc1ccc(cc1)C[C@@H]3N(C)CC2)N(C)CC4

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL504323
Name	BERBAMINE
Phase	Preclinical
Structure Type	MOL
InChI Key	DFOCUWZXJBAUSQ-URLMMPGGSA-N

NSC-369310

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

608.7

MW (Da)

6.86

ALogP

HBA

HBD

72.9

PSA (Å²)

0.27

QED

Ro5 Violations

Rot. Bonds

Natural Product First in Class Prodrug

IC50 8 meas. best 6.89

Ki 3 meas. best 6.72

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Plasmodium falciparum CHEMBL364	IC50	6.89	6.695	128.0	2
Muscarinic acetylcholine receptor CHEMBL1907609	Ki	6.72	6.72	190.0	1
Small conductance calcium-activated potassium channel protein 2 CHEMBL4469	Ki	6.55	6.55	284.0	1
Small conductance calcium-activated potassium channel protein 3 CHEMBL3381	Ki	6.17	6.17	679.0	1
SARS-CoV-2 CHEMBL4303835	IC50	5.1	5.1	7870.0	1
K562 CHEMBL385	IC50	5.05	4.9267	8930.0	3
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A CHEMBL3421	IC50	4.66	4.66	22000.0	1
Unchecked CHEMBL612545	IC50	4.22	4.22	60000.0	1

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Plasmodium falciparum	IC50	=	128.0	nM	6.89	Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D6 i...	9917283
Muscarinic acetylcholine receptor	Ki	=	190.0	nM	6.72	Displacement of [3H]QNB from rat brain muscarinic receptor	1955879
Small conductance calcium-activated potassium channel protein 2	Ki	=	284.0	nM	6.55	Displacement of [125I]apamin from human SK2 expressed in HEK293 cells assessed a...	38352826
Plasmodium falciparum	IC50	=	313.0	nM	6.5	Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 i...	9917283
Small conductance calcium-activated potassium channel protein 3	Ki	=	679.0	nM	6.17	Displacement of [125I]apamin from human SK3 expressed in HEK293 cells assessed a...	38352826
SARS-CoV-2	IC50	=	7870.0	nM	5.1	Antiviral activity against SARS-CoV-2 (viral titer) measured by plaque assay in ...	-
K562	IC50	=	8930.0	nM	5.05	Cytotoxicity against human imatinib-resistant K562 leukemia cells expressing p21...	19285759
K562	IC50	=	11100.0	nM	4.96	Antiproliferative activity against imatinib resistant human K562 cells assessed ...	35551036
K562	IC50	=	17100.0	nM	4.77	Antiproliferative activity against imatinib resistant human K562 cells assessed ...	35551036
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A	IC50	=	22000.0	nM	4.66	Inhibition of calmodulin-dependent phosphodiesterase	1955879
Unchecked	IC50	=	60000.0	nM	4.22	Inhibition of calmodulin-stimulated Ca2+/Mg2+ ATPase activity in human erythrocy...	1955879

PubMed	DOI	Target Context	# Activities
19285759	10.1016/j.ejmech.2009.02.018	K562	5
22766217	10.1016/j.bmc.2012.06.017	U-937	4
35551036	10.1016/j.ejmech.2022.114442	Unchecked	4
32503690	10.1016/j.bmc.2020.115553	ATP-dependent translocase ABCB1	3
35551036	10.1016/j.ejmech.2022.114442	K562	2
1955879	10.1021/np50075a001	Unchecked	2
9917283	10.1021/np980144f	Plasmodium falciparum	2
9917283	10.1021/np980144f	Unchecked	2
-	10.1101/2020.03.20.999730	SARS-CoV-2	1
30701972	10.1021/acs.jnatprod.8b00592	Glycogen synthase kinase-3 beta	1
38352826	10.1021/acsmedchemlett.3c00452	Unchecked	1
30701972	10.1021/acs.jnatprod.8b00592	Acetylcholinesterase	1
30701972	10.1021/acs.jnatprod.8b00592	Cholinesterase	1
30701972	10.1021/acs.jnatprod.8b00592	Unchecked	1
-	10.1101/2020.03.20.999730	ADMET	1
-	10.1101/2020.03.20.999730	Vero	1
1955879	10.1021/np50075a001	Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A	1
-	10.1039/C0MD00241K	Telomerase reverse transcriptase	1
-	10.1007/s00044-011-9767-1	Entamoeba histolytica	1
9917283	10.1021/np980144f	KB	1

Data from ChEMBL 36 via Core Engine