Harmine

Representations & DB's id
ChEBI:	CHEBI:28121
ChEMBL:	CHEMBL269538
PubChem:	5280953
IUPAC:	7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
Standard InChI:	InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
Standard InChI Key:	BXNJHAXVSOCGBA-UHFFFAOYSA-N
SMILES:	COc1ccc2c(c1)[nH]c1c2ccnc1C

Molecular propeties
AlogP:	3.03
Hydrogen bonds acceptors:	2
Hydrogen bonds donors:	1
Rotatable bonds:	1
Number of rings:	3
Molecular Weight:	212.09
Topological polar surface area:	37.9
Number of aromatic rings:	3
Fsp3:	0.154
Number of carbons:	13

Plant sources

Part of plant	Plant name	Ref.
Seed	Peganum harmala

In vitro data

Activity Type	Activity Value	Target Name	UniProt ID
Ki	50000 nM	Cytochrome P450 2D6	P10635
Ki	22 nM	Nischarin	Q9Y2I1
Others	92.1 %	Sphingomyelin phosphodiesterase	P17405
Others	80 %	Rho-associated protein kinase 2	O75116
Others	105 %	Ribosomal protein S6 kinase alpha 1	Q15418
Others	103 %	MAP kinase p38 beta	Q15759
Others	88 %	MAP kinase p38 delta	O15264
Others	80 %	MAP kinase p38 gamma	P53778
Others	96 %	Serine/threonine-protein kinase PAK 4	O96013
Others	92 %	Serine/threonine-protein kinase PAK7	Q9P286
Others	83 %	Serine/threonine-protein kinase PAK6	Q9NQU5
Others	87 %	3-phosphoinositide dependent protein kinase-1	O15530
Others	86 %	Serine/threonine-protein kinase PIM1	P11309
Others	88 %	Serine/threonine-protein kinase PIM2	Q9P1W9
Others	64 %	Serine/threonine-protein kinase PIM3	Q86V86
Others	80 %	cAMP-dependent protein kinase alpha-catalytic subunit	P17612
Others	101 %	Serine/threonine-protein kinase AKT	P31749
Others	90 %	Serine/threonine-protein kinase AKT2	P31751
Others	82 %	Protein kinase C alpha	P17252
Others	83 %	Protein kinase C zeta	Q05513
Others	80 %	Protein kinase C mu	Q15139
Others	86 %	Serine/threonine-protein kinase SRPK1	Q96SB4
Others	104 %	Ribosomal protein S6 kinase alpha 3	P51812
Others	93 %	Ribosomal protein S6 kinase 1	P23443
Others	83 %	Serine/threonine-protein kinase Sgk1	O00141
Others	87 %	Myosin light chain kinase, smooth muscle	Q15746
IC50	1500 nM	Casein kinase I delta	P48730
IC50	80 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	900 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Q92630
IC50	800 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 3	O43781
IC50	4300 nM	Serine/threonine-protein kinase PIM3	Q86V86
Others	81 %	Serine/threonine-protein kinase Aurora-B	Q96GD4
Others	83 %	Serine/threonine-protein kinase Aurora-C	Q9UQB9
Others	83 %	BR serine/threonine-protein kinase 2	Q8IWQ3
Others	94 %	CaM kinase I alpha	Q14012
Others	95 %	CaM-kinase kinase alpha	Q8N5S9
Others	81 %	CaM-kinase kinase beta	Q96RR4
Others	99 %	Serine/threonine-protein kinase Chk1	O14757
Others	100 %	Serine/threonine-protein kinase Chk2	O96017
Others	60 %	Casein kinase I delta	P48730
Others	86 %	Tyrosine-protein kinase CSK	P41240
Others	4 %	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
Others	15 %	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Q92630
Others	6 %	Dual-specificity tyrosine-phosphorylation regulated kinase 3	O43781
Others	104 %	Serine/threonine-protein kinase EEF2K	O00418
Others	95 %	MAP kinase ERK1	P27361
Others	95 %	MAP kinase ERK2	P28482
Others	80 %	Mitogen-activated protein kinase 15	Q8TD08
Others	85 %	Serine/threonine-protein kinase MST2	Q13188
Others	94 %	Serine/threonine-protein kinase NEK2	P51955
Others	87 %	Serine/threonine-protein kinase NEK6	Q9HC98
Others	108 %	Serine/threonine-protein kinase NEK7	Q8TDX7
Others	100 %	MAP kinase p38 alpha	Q16539
Others	87 %	Glycogen synthase kinase-3 beta	P49841
Others	108 %	Homeodomain-interacting protein kinase 2	Q9H2X6
Others	87 %	Homeodomain-interacting protein kinase 3	Q9H422
Others	73 %	Inhibitor of nuclear factor kappa B kinase beta subunit	O14920
Others	91 %	c-Jun N-terminal kinase 2	P45984
Others	91 %	c-Jun N-terminal kinase 3	P53779
Others	110 %	MAP kinase-activated protein kinase 2	P49137
Others	98 %	MAP kinase-activated protein kinase 3	Q16644
Others	89 %	c-Jun N-terminal kinase 1	P45983
Others	83 %	Serine/threonine-protein kinase c-TAK1	P27448
Others	8 %	Maternal embryonic leucine zipper kinase	Q14680
Others	73 %	Dual specificity mitogen-activated protein kinase kinase 1	Q02750
Others	82 %	MAP kinase-interacting serine/threonine-protein kinase MNK1	Q9BUB5
Others	80 %	MAP kinase signal-integrating kinase 2	Q9HBH9
Others	83 %	Ribosomal protein S6 kinase alpha 5	O75582
Others	97 %	Serine/threonine-protein kinase PLK1	P53350
Others	90 %	MAP kinase-activated protein kinase 5	Q8IW41
Others	86 %	Protein kinase N2	Q16513
Ki	5 nM	Monoamine oxidase A	P21397
Potency	12589.3 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	25118.9 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	12589.3 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	15848.9 nM	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Q99714
Potency	28183.8 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	28183.8 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	14125.4 nM	Lysine-specific demethylase 4D-like	B2RXH2
Potency	3548.1 nM	Survival motor neuron protein	Q16637
Potency	3162.3 nM	Survival motor neuron protein	Q16637
Potency	8912.5 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	6309.6 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	5623.4 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	31622.8 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	28183.8 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	11220.2 nM	Aldehyde dehydrogenase 1A1	P00352
Potency	6309.6 nM	Hypoxia-inducible factor 1 alpha	Q16665
Potency	31622.8 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	28183.8 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	7943.3 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	5011.9 nM	15-hydroxyprostaglandin dehydrogenase [NAD+]	P15428
Potency	7943.3 nM	Cytochrome P450 2D6	P10635
Potency	39810.7 nM	Cytochrome P450 3A4	P08684
Potency	15848.9 nM	Cytochrome P450 3A4	P08684
Potency	10000 nM	Cytochrome P450 3A4	P08684
Potency	39810.7 nM	Cytochrome P450 3A4	P08684
Potency	15848.9 nM	Cytochrome P450 3A4	P08684
Potency	10000 nM	Cytochrome P450 3A4	P08684
Ki	16.9 nM	Monoamine oxidase A	P21397
Ki	120800 nM	Monoamine oxidase B	P27338
Potency	23109.3 nM	Nuclear factor erythroid 2-related factor 2	Q16236
Potency	15848.9 nM	Histone acetyltransferase GCN5	Q92830
Potency	15848.9 nM	Arachidonate 15-lipoxygenase, type II	O15296
Potency	67.1 nM	Dual specificity protein kinase CLK4	Q9HAZ1
IC50	590 nM	Serine/threonine-protein kinase haspin	Q8TF76
Others	23.75 %	Acetylcholinesterase	P22303
Potency	10000 nM	Ataxin-2	Q99700
IC50	80 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	10000 nM	Serine/threonine-protein kinase PIM1	P11309
IC50	10000 nM	Glycogen synthase kinase-3 beta	P49841
IC50	10000 nM	Glycogen synthase kinase-3 alpha	P49840
IC50	9500 nM	Dual specificity tyrosine-phosphorylation-regulated kinase 4	Q9NR20
IC50	210 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 3	O43781
IC50	120 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Q92630
IC50	28 nM	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Q9Y463
IC50	60 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	85 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	800 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 3	O43781
IC50	900 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Q92630
IC50	80 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	26 nM	Dual specificty protein kinase CLK1	P49759
Ki	33 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
Ki	166 nM	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Q9Y463
IC50	33 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	60 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	74000 nM	Dual specificity tyrosine-phosphorylation-regulated kinase 4	Q9NR20
IC50	2000 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Q92630
IC50	166 nM	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Q9Y463
IC50	33 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	80 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	220 nM	Dual specificty protein kinase CLK1	P49759
IC50	3000 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Q92630
IC50	180 nM	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Q9Y463
IC50	130 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627
IC50	400 nM	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Q13627

Harmine

Representations & DB's id

Molecular propeties

Plant sources

In vitro data