Compound Detail

CHEMBL340807

HARMALINE

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COc1ccc2c3c([nH]c2c1)C(C)=NCC3

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL340807
Name	HARMALINE
Phase	Preclinical
Structure Type	MOL
InChI Key	RERZNCLIYCABFS-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

214.3

MW (Da)

2.54

ALogP

HBA

HBD

37.4

PSA (Å²)

0.78

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C13H14N2O
MW	214.27
Aromatic Rings	2
Heavy Atoms	16
NP-Likeness	0.72

Activity Summary

IC50 15 meas. best 8.6

Ki 4 meas. best 5.82

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	8.6	8.04	2.5	2
Amine oxidase [flavin-containing] A CHEMBL3358	IC50	7.92	7.92	12.0	1
Leishmania donovani CHEMBL367	IC50	5.94	5.94	1160.0	1
Leishmania infantum CHEMBL612848	IC50	5.94	5.94	1160.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	5.82	5.82	1500.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	5.34	5.34	4600.0	1
Acetylcholinesterase CHEMBL4078	IC50	5.31	5.31	4900.0	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	5.3	5.3	5000.0	1
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	5.26	5.26	5500.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	5.03	5.03	9400.0	1
Acetylcholinesterase CHEMBL220	IC50	4.62	4.62	23700.0	1
Leishmania amazonensis CHEMBL612877	IC50	4.0	4.0	99000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Amine oxidase [flavin-containing] A	IC50	=	2.5	nM	8.6	Inhibition of MAO-A (unknown origin)	33528252
Amine oxidase [flavin-containing] A	IC50	=	12.0	nM	7.92	In vitro inhibitory activity against rat brain Monoamine oxidase A	7490728
Amine oxidase [flavin-containing] A	IC50	=	32.9	nM	7.48	Inhibition of recombinant human MAO-A expressed in baculovirus infected BTI-TN-5...	33071056
Leishmania infantum	IC50	=	1160.0	nM	5.94	Antimicrobial activity against amastigote stage of Leishmania infantum	24980054
Leishmania donovani	IC50	=	1160.0	nM	5.94	Antimicrobial activity against axenic amastigote stage of Leishmania donovani af...	24980054
5-hydroxytryptamine receptor 6	Ki	=	1500.0	nM	5.82	Binding affinity to 5-HT6R (unknown origin) assessed as inhibition constant	33528252
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	4600.0	nM	5.34	Inhibition of DYRK1A (unknown origin)	33528252
Acetylcholinesterase	IC50	=	4900.0	nM	5.31	Inhibition of electric eel AChE using acetylcholine iodide as substrate measured...	22425563
5-hydroxytryptamine receptor 2A	Ki	=	5000.0	nM	5.3	Displacement of [3H]-LSD from human 5-HT2A expressed in human HEK cells assessed...	33528252
5-hydroxytryptamine receptor 7	Ki	=	5500.0	nM	5.26	Displacement of [3H]-citalopram from human 5-HT7 expressed in human HEK cells as...	33528252
5-hydroxytryptamine receptor 2C	Ki	=	9400.0	nM	5.03	Displacement of [3H]-LSD from human 5-HT2C expressed in human HEK cells assessed...	33528252
Acetylcholinesterase	IC50	=	23700.0	nM	4.62	Inhibition of human AChE by Ellman's method	22425563
Leishmania amazonensis	IC50	=	99000.0	nM	4.0	Antileishmanial activity against Leishmania mexicana amazonensis promastigotes	18558492

Literature References

PubMed	DOI	Target Context	# Activities
6195312	10.1021/np50028a027	CHO	8
22425563	10.1016/j.bmcl.2012.02.057	Acetylcholinesterase	4
24980054	10.1016/j.bmcl.2014.06.030	Leishmania infantum	2
17850214	10.1042/bj20070797	Unchecked	2
24980054	10.1016/j.bmcl.2014.06.030	Leishmania donovani	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
17850214	10.1042/bj20070797	Rho-associated protein kinase 2	1
17850214	10.1042/bj20070797	3-phosphoinositide-dependent protein kinase 1	1
17850214	10.1042/bj20070797	Serine/threonine-protein kinase PAK 6	1
17850214	10.1042/bj20070797	Serine/threonine-protein kinase PAK 4	1
17850214	10.1042/bj20070797	Mitogen-activated protein kinase 12	1
17850214	10.1042/bj20070797	Mitogen-activated protein kinase 13	1
17850214	10.1042/bj20070797	Mitogen-activated protein kinase 11	1
38318365	10.1016/j.isci.2024.108907	Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	1
18558492	10.1016/j.bmc.2008.05.074	Leishmania infantum	1
18558492	10.1016/j.bmc.2008.05.074	Trypanothione reductase	1
11909733	10.1016/s0960-894x(02)00094-x	Cyclin-dependent kinase 2	1
11909733	10.1016/s0960-894x(02)00094-x	Cyclin-dependent kinase 5	1
7490728	10.1021/jm00024a006	Unchecked	1
7490728	10.1021/jm00024a006	Amine oxidase [flavin-containing] B	1

Data from ChEMBL 36 via Core Engine