Compound Detail

CHEMBL50588

EMETINE

💊 Approved Drug

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💊 Approved Drug

CC[C@H]1CN2CCc3cc(OC)c(OC)cc3[C@@H]2C[C@@H]1C[C@H]1NCCc2cc(OC)c(OC)cc21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL50588
Name	EMETINE
Phase	Approved
Structure Type	MOL
InChI Key	AUVVAXYIELKVAI-CKBKHPSWSA-N

Known Names

(-)-emetine 6',7',10,11-tetramethoxyemetan Cephaeline methyl ether Emetan, 6',7',10,11-tetramethoxy- Emetin Emetine Emetinum GNF-Pf-196 NSC-33669 TCMDC-125531

Targets

126

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

480.6

MW (Da)

4.94

ALogP

HBA

HBD

52.2

PSA (Å²)

0.61

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Withdrawn
Chirality	Single Enantiomer

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula	C29H40N2O4
MW	480.65
Aromatic Rings	2
Heavy Atoms	35
NP-Likeness	0.96

Indications

Amebiasis

ATC Classification

P01AX02

emetine

Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

Level 2: ANTIPROTOZOALS

P01AX52

emetine, combinations

Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

Level 2: ANTIPROTOZOALS

Drug Warnings

Withdrawn

General Warning

Harmful

Country: Mauritius Year: 1982

Activity Summary

IC50 113 meas. best 9.72

EC50 8 meas. best 8.06

Ki 5 meas. best 7.85

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
CHO CHEMBL613853	IC50	9.72	7.0851	0.2	39
Unchecked CHEMBL612545	IC50	9.0	7.6782	1.0	11
P388 CHEMBL389	IC50	8.15	8.15	7.0	1
Plasmodium yoelii CHEMBL612889	IC50	8.13	8.13	7.5	1
NS5 CHEMBL4523952	EC50	8.06	7.67	8.7	2
HEK293 CHEMBL614818	IC50	8.0	8.0	10.0	1
Plasmodium falciparum CHEMBL364	EC50	7.99	7.815	10.2	2
HeLa CHEMBL399	IC50	7.89	7.135	13.0	4
Alpha-2A adrenergic receptor CHEMBL1867	Ki	7.85	7.85	14.0	1
CHO-K1 CHEMBL614031	IC50	7.7	7.05	20.0	2
DU-145 CHEMBL613508	IC50	7.62	7.48	24.0	4
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.58	7.58	26.0	1
LNCaP CHEMBL612518	IC50	7.57	7.4825	27.0	4
PC-3 CHEMBL390	IC50	7.57	7.525	27.0	4
CWR22R CHEMBL612657	IC50	7.51	7.51	30.8	1
HT-29 CHEMBL384	IC50	7.48	7.48	33.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	7.42	7.42	38.0	1
Trypanosoma brucei CHEMBL612849	IC50	7.4	7.4	40.0	1
A549 CHEMBL392	IC50	7.4	7.4	40.0	1
KB CHEMBL398	IC50	7.4	7.325	40.0	2
ADMET CHEMBL612558	IC50	7.3	7.3	50.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.3	6.92	50.0	2
Vero CHEMBL391	IC50	7.1	6.9833	80.0	3
Glucose transporter CHEMBL3431938	IC50	7.09	7.09	81.0	1
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha CHEMBL2221345	IC50	7.08	7.02	83.0	2
Hexose transporter 1 CHEMBL4697	IC50	7.05	7.05	90.0	1
ZR-75-1 CHEMBL614393	IC50	7.0	7.0	100.0	1
Solute carrier family 2, facilitated glucose transporter member 1 CHEMBL2535	IC50	6.97	6.97	108.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	6.74	6.74	182.0	1
Vaccinia virus CHEMBL613493	EC50	6.6	6.6	250.0	1
Human coronavirus OC43 CHEMBL5209665	EC50	6.52	6.52	300.0	1
G-protein coupled receptor 35 CHEMBL1293267	IC50	6.45	6.45	352.5	1
Trypanosoma congolense CHEMBL4296607	IC50	6.37	6.37	430.0	1
Giardia intestinalis CHEMBL612652	IC50	6.1	6.0867	800.0	3
Alpha-1B adrenergic receptor CHEMBL315	Ki	5.97	5.97	1071.0	1
Unchecked CHEMBL612545	EC50	5.84	5.84	1430.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	5.71	5.71	1934.0	1
Unchecked CHEMBL612545	Ki	5.68	5.68	2094.0	1
Entamoeba histolytica CHEMBL612853	IC50	5.66	5.66	2180.0	3
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	5.62	5.035	2400.0	4
Alpha-1A adrenergic receptor CHEMBL319	Ki	5.58	5.58	2642.0	1
Alpha-1A adrenergic receptor CHEMBL319	IC50	5.18	5.18	6527.0	1
SARS-CoV-2 CHEMBL4303835	EC50	5.11	5.11	7710.0	1
Serine hydrolase RBBP9 CHEMBL1075121	IC50	5.11	5.11	7800.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
CHO	IC50	=	0.19	nM	9.72	Cytotoxicity against CHO cells by MTT assay	20971006
Unchecked	IC50	=	1.0	nM	9.0	PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co...	-
Unchecked	IC50	=	1.0	nM	9.0	PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (...	-
Unchecked	IC50	=	2.28	nM	8.64	PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c...	-
P388	IC50	=	7.0	nM	8.15	Antiproliferative activity against mouse P388 cells after 48 hrs by MTT assay	2778449
Plasmodium yoelii	IC50	=	7.49	nM	8.13	NOVARTIS: Antimalarial liver stage activity measured as reduction in Plasmodium ...	22096101
Unchecked	IC50	=	8.31	nM	8.08	PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf...	-
NS5	EC50	=	8.74	nM	8.06	Inhibition of RNA-dependent RNA polymerase in Zika virus PRVABC59 infected in Af...	31549836
HEK293	IC50	=	10.0	nM	8.0	Cytotoxicity against HEK293 cells assessed as inhibition of cell growth incubate...	36516584
Plasmodium falciparum	EC50	=	10.15	nM	7.99	NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati...	18579783
Unchecked	IC50	=	11.58	nM	7.94	PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co...	-
HeLa	IC50	=	13.0	nM	7.89	Cytotoxicity against human HeLa cells assessed as inhibition of cell viability i...	31952962
Alpha-2A adrenergic receptor	Ki	=	14.0	nM	7.85	DRUGMATRIX: Alpha-2A adrenergic receptor radioligand binding (ligand: MK-912)	-
HeLa	IC50	=	15.0	nM	7.82	Cytotoxicity against human HeLa cells assessed as reduction in cell viability af...	30881619
CHO	IC50	=	16.2	nM	7.79	Cytotoxicity against CHO cells measured after 48 hrs by MTT assay	31301563
Unchecked	IC50	=	16.34	nM	7.79	PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co...	-
CHO	IC50	=	20.0	nM	7.7	Cytotoxicity against CHO cells assessed as inhibition of cell viability by MTT a...	33844521
CHO-K1	IC50	=	20.0	nM	7.7	Cytotoxicity against CHOK1 cells assessed as reduction in cell viability incubat...	31303994
CHO	IC50	=	19.77	nM	7.7	Cytotoxicity against CHO cells by MTT assay	22750008
Unchecked	IC50	=	22.1	nM	7.66	PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	296
-	10.6019/CHEMBL5058564	HEK-293T	9
21051535	10.1124/dmd.110.034629	ADMET	9
-	10.6019/CHEMBL5058564	Fibroblast	9
-	10.6019/CHEMBL5058564	U2OS	9
11602674	-	ATP-dependent translocase ABCB1	7
11716514	10.1006/bbrc.2001.6000	ATP-dependent translocase ABCB1	7
15974627	10.1021/np050029m	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	6
-	10.6019/CHEMBL5209801	Type-1 angiotensin II receptor	5
29185748	10.1021/acs.jmedchem.7b01537	Plasmodium falciparum	5
-	10.6019/CHEMBL5209801	Alpha-2A adrenergic receptor	5
-	10.6019/CHEMBL5209801	Beta-2 adrenergic receptor	5
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	5
-	10.6019/CHEMBL5209801	Glucagon-like peptide 1 receptor	5
-	10.6019/CHEMBL5209801	Apelin receptor	5
-	10.6019/CHEMBL5209801	N-formyl peptide receptor 2	5
-	10.6019/CHEMBL5209801	C5a anaphylatoxin chemotactic receptor 1	5
-	10.6019/CHEMBL5209801	Free fatty acid receptor 4	5
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	5
-	10.6019/CHEMBL5209801	Sphingosine 1-phosphate receptor 1	5

Data from ChEMBL 36 via Core Engine