Compound Detail

CHEMBL269538

HARMINE

Phase I

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Phase I

COc1ccc2c(c1)[nH]c1c(C)nccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL269538
Name	HARMINE
Phase	Phase I
Structure Type	MOL
InChI Key	BXNJHAXVSOCGBA-UHFFFAOYSA-N

Known Names

Harmine

Targets

280

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

212.2

MW (Da)

3.03

ALogP

HBA

HBD

37.9

PSA (Å²)

0.67

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

Extended Properties

Molecular Formula	C13H12N2O
MW	212.25
Aromatic Rings	3
Heavy Atoms	16
NP-Likeness	0.29

Indications

Diabetes Mellitus

Activity Summary

IC50 252 meas. best 9.0

Ki 20 meas. best 9.0

EC50 4 meas. best 6.28

Kd 4 meas. best 8.26

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Amine oxidase [flavin-containing] A CHEMBL1951	Ki	9.0	8.21	1.0	4
Amine oxidase [flavin-containing] A CHEMBL1951	IC50	9.0	8.3083	1.0	6
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Kd	8.26	8.065	5.5	2
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	IC50	8.05	7.2533	8.8	39
Dual specificity protein kinase CLK1 CHEMBL4224	Kd	7.92	7.92	12.1	1
Nischarin CHEMBL3923	Ki	7.66	6.26	22.0	2
Dual specificity protein kinase CLK4 CHEMBL4203	IC50	7.62	7.305	24.0	2
Dual specificity protein kinase CLK1 CHEMBL4224	IC50	7.58	7.0167	26.0	6
Plasmodium falciparum CHEMBL364	IC50	7.55	5.7278	28.0	9
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	IC50	7.55	7.0011	28.0	9
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL5508	IC50	7.54	7.42	29.0	3
Dual specificity tyrosine-phosphorylation-regulated kinase 1A CHEMBL2292	Ki	7.48	7.48	33.0	1
Unchecked CHEMBL612545	Ki	7.31	7.31	49.0	1
Dual specificity protein kinase CLK4 CHEMBL1075283	IC50	7.3	7.3	50.0	1
Dual specificity protein kinase CLK1 CHEMBL1075280	IC50	7.14	7.14	72.0	1
Dual specificity protein kinase CLK2 CHEMBL4225	IC50	6.92	6.43	120.0	2
Dual specificity tyrosine-phosphorylation-regulated kinase 2 CHEMBL4376	IC50	6.92	5.9792	120.0	13
Dual specificity tyrosine-phosphorylation-regulated kinase 1B CHEMBL5543	Ki	6.78	6.78	166.0	1
Dual specificity tyrosine-phosphorylation-regulated kinase 3 CHEMBL4575	IC50	6.68	6.2271	210.0	7
Leishmania infantum CHEMBL612848	IC50	6.64	5.8333	230.0	3
Leishmania donovani CHEMBL367	IC50	6.64	6.035	230.0	2
Dual specificity protein kinase CLK2 CHEMBL1075281	IC50	6.55	6.55	280.0	1
Glycogen synthase kinase-3 beta CHEMBL262	IC50	6.46	5.1467	350.0	3
Human immunodeficiency virus 1 CHEMBL378	EC50	6.28	6.28	520.0	1
Serine/threonine-protein kinase haspin CHEMBL1075163	IC50	6.23	6.23	590.0	3
CDK9/cyclin T1 CHEMBL2111389	IC50	6.14	6.14	720.0	1
Cyclin-dependent kinase 9 CHEMBL3116	IC50	6.14	6.14	720.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.09	6.09	810.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	5.95	5.95	1130.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	5.83	5.83	1480.0	1
Unchecked CHEMBL612545	IC50	5.82	5.292	1500.0	5
Casein kinase I isoform delta CHEMBL2828	IC50	5.82	5.82	1500.0	1
Casein kinase I delta/epsilon CHEMBL3038494	IC50	5.82	5.82	1500.0	1
Rho-associated protein kinase 1 CHEMBL3231	IC50	5.82	5.82	1500.0	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.59	5.59	2540.0	1
Dual specificity protein kinase CLK3 CHEMBL4226	IC50	5.52	5.285	3000.0	2
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.49	5.49	3260.0	1
Glycogen synthase kinase-3 beta CHEMBL262	Kd	5.45	5.45	3560.0	1
HGC-27 CHEMBL1075463	IC50	5.45	5.45	3520.0	1
HT-29 CHEMBL384	IC50	5.45	4.9167	3520.0	3
MCF7 CHEMBL387	IC50	5.45	4.69	3520.0	9
PC-3 CHEMBL390	IC50	5.45	5.13	3520.0	2
Chitinase CHEMBL1795119	Ki	5.42	5.42	3780.0	1
Serine/threonine-protein kinase pim-3 CHEMBL5407	IC50	5.37	5.37	4300.0	2
Broad substrate specificity ATP-binding cassette transporter ABCG2 CHEMBL5393	IC50	5.29	5.29	5080.0	1
A549 CHEMBL392	IC50	5.28	4.8286	5230.0	7
5-hydroxytryptamine receptor 7 CHEMBL3155	Ki	5.26	5.26	5500.0	1
HCT-116 CHEMBL394	IC50	5.16	4.61	6940.0	6
Chitinase CHEMBL1795119	IC50	5.15	5.15	7060.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	5.14	4.4557	7200.0	7

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Amine oxidase [flavin-containing] A	Ki	=	1.0	nM	9.0	Binding affinity to MAO-A (unknown origin) assessed as inhibition constant	33528252
Amine oxidase [flavin-containing] A	IC50	=	1.0	nM	9.0	Inhibition of MAO-A (unknown origin)	33528252
Amine oxidase [flavin-containing] A	IC50	=	4.1	nM	8.39	Inhibition of recombinant human MAO-A using using kynuramine as substrate assess...	36307034
Amine oxidase [flavin-containing] A	IC50	=	4.1	nM	8.39	Inhibition of human recombinant MAO-A assessed as inhibition of 4-hydroxyquinoli...	36179486
Amine oxidase [flavin-containing] A	IC50	=	4.1	nM	8.39	Inhibition of human recombinant MAO-A assessed as inhibition of 4-hydroxyquinoli...	36244185
Amine oxidase [flavin-containing] A	Ki	=	5.0	nM	8.3	Inhibition of human MAOA	19969454
Amine oxidase [flavin-containing] A	IC50	=	5.0	nM	8.3	Inhibition of MAOA (unknown origin)	35863237
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Kd	=	5.474	nM	8.26	Binding affinity to human DYRK1A assessed as equilibrium dissociation constant m...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	8.81	nM	8.05	Inhibition of GST-tagged human recombinant DYRK1A by FRET-based LanthaScreen Eu ...	30059217
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	12.0	nM	7.92	Inhibition of N-terminal GST-fused full-length human DYRK1A (1 to 763 residues) ...	34954592
Dual specificity protein kinase CLK1	Kd	=	12.11	nM	7.92	Binding affinity to human CLK1 assessed as equilibrium dissociation constant mea...	36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Kd	=	13.4	nM	7.87	Binding affinity to human C-terminal his tagged DYRK1A (26 to 490 residues) expr...	36883902
Amine oxidase [flavin-containing] A	Ki	=	16.9	nM	7.77	Inhibition of human recombinant MAO-A expressed in baculovirus-infected Bacillus...	21183355
Amine oxidase [flavin-containing] A	Ki	=	17.0	nM	7.77	Inhibition of MAO-A	21726069
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	20.5	nM	7.69	Inhibition of DYRK1A (unknown origin) using DYRKtide as substrate incubated for ...	38648167
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	21.83	nM	7.66	Inhibition of human DYRK1A using [33P]-ATP incubated for 120 mins	27766861
Dual specificity tyrosine-phosphorylation-regulated kinase 1A	IC50	=	22.0	nM	7.66	Inhibition of DYRK1A (unknown origin)	33528252
Nischarin	Ki	=	22.0	nM	7.66	Binding affinity towards Imidazoline I2 receptor	14643338
Dual specificity protein kinase CLK4	IC50	=	24.0	nM	7.62	Inhibition of CLK4 (unknown origin)	33528252
Dual specificity protein kinase CLK1	IC50	=	26.0	nM	7.58	Inhibition of GST-tagged human recombinant CLK1 expressed in Escherichia coli us...	27676471

Literature References

PubMed	DOI	Target Context	# Activities
38069814	10.1021/acs.jmedchem.3c01326	Echinococcus granulosus	25
35450378	10.1021/acsmedchemlett.1c00630	CAL-27	15
32787089	10.1021/acs.jmedchem.0c00354	HT-29	9
38069814	10.1021/acs.jmedchem.3c01326	ADMET	8
30851694	10.1016/j.ejmech.2019.02.054	Bel7402/5-FU	7
32003560	10.1021/acs.jmedchem.9b01379	ADMET	7
22998443	10.1021/jm301034u	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	6
36883902	10.1021/acs.jmedchem.2c01887	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	5
22998443	10.1021/jm301034u	Unchecked	5
38154256	10.1016/j.ejmech.2023.116061	MCF7	5
36876904	10.1021/acs.jmedchem.2c02068	Unchecked	5
30059217	10.1021/acs.jmedchem.8b00658	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	5
27280693	10.1021/acs.jmedchem.6b00035	Broad substrate specificity ATP-binding cassette transporter ABCG2	5
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity protein kinase CLK1	4
10612592	10.1016/s0960-894x(99)00598-3	KB	4
36876904	10.1021/acs.jmedchem.2c02068	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	4
22425563	10.1016/j.bmcl.2012.02.057	Acetylcholinesterase	4
20349996	10.1021/jm901796s	Plasmodium falciparum	4
29985601	10.1021/acs.jmedchem.8b00185	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	4
35551033	10.1016/j.ejmech.2022.114408	Plasmodium falciparum	4

Data from ChEMBL 36 via Core Engine