Harmine
| Internal ID | 5303cf7a-5199-420c-807a-08db60086f25 |
| Taxonomy | Alkaloids and derivatives > Harmala alkaloids |
| IUPAC Name | 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole |
| SMILES (Canonical) | CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC |
| SMILES (Isomeric) | CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC |
| 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 |
| InChI Key | BXNJHAXVSOCGBA-UHFFFAOYSA-N |
| Popularity | 2,070 references in papers |
| Molecular Formula | C13H12N2O |
| Molecular Weight | 212.25 g/mol |
| Exact Mass | 212.094963011 g/mol |
| Topological Polar Surface Area (TPSA) | 37.90 Ų |
| XlogP | 3.60 |
| Atomic LogP (AlogP) | 3.03 |
| H-Bond Acceptor | 2 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 1 |
| 442-51-3 |
| 7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole |
| Banisterine |
| Telepathine |
| Leucoharmine |
| Yageine |
| Yajeine |
| 9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl- |
| 7-Methoxy-1-methyl-9H-beta-carboline |
| Harmin |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 1.0000 | 100.00% |
| Caco-2 | - | 0.9373 | 93.73% |
| Blood Brain Barrier | + | 0.7879 | 78.79% |
| Human oral bioavailability | + | 0.6429 | 64.29% |
| Subcellular localzation | Mitochondria | 0.8289 | 82.89% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9545 | 95.45% |
| OATP1B3 inhibitior | + | 0.9509 | 95.09% |
| MATE1 inhibitior | - | 0.9200 | 92.00% |
| OCT2 inhibitior | - | 0.8000 | 80.00% |
| BSEP inhibitior | + | 0.5524 | 55.24% |
| P-glycoprotein inhibitior | - | 0.9379 | 93.79% |
| P-glycoprotein substrate | - | 0.6866 | 68.66% |
| CYP3A4 substrate | - | 0.5228 | 52.28% |
| CYP2C9 substrate | - | 0.7825 | 78.25% |
| CYP2D6 substrate | - | 0.6664 | 66.64% |
| CYP3A4 inhibition | + | 0.6929 | 69.29% |
| CYP2C9 inhibition | - | 0.9481 | 94.81% |
| CYP2C19 inhibition | - | 0.9026 | 90.26% |
| CYP2D6 inhibition | + | 0.8932 | 89.32% |
| CYP1A2 inhibition | + | 0.9629 | 96.29% |
| CYP2C8 inhibition | + | 0.5260 | 52.60% |
| CYP inhibitory promiscuity | + | 0.6307 | 63.07% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.9823 | 98.23% |
| Carcinogenicity (trinary) | Non-required | 0.4942 | 49.42% |
| Eye corrosion | - | 0.9899 | 98.99% |
| Eye irritation | + | 0.7751 | 77.51% |
| Skin irritation | - | 0.8323 | 83.23% |
| Skin corrosion | - | 0.9609 | 96.09% |
| Ames mutagenesis | + | 0.8800 | 88.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4124 | 41.24% |
| Micronuclear | + | 0.8000 | 80.00% |
| Hepatotoxicity | + | 0.5638 | 56.38% |
| skin sensitisation | - | 0.9251 | 92.51% |
| Respiratory toxicity | - | 0.6111 | 61.11% |
| Reproductive toxicity | + | 0.6889 | 68.89% |
| Mitochondrial toxicity | - | 0.7000 | 70.00% |
| Nephrotoxicity | - | 0.8725 | 87.25% |
| Acute Oral Toxicity (c) | III | 0.6254 | 62.54% |
| Estrogen receptor binding | + | 0.8701 | 87.01% |
| Androgen receptor binding | + | 0.8462 | 84.62% |
| Thyroid receptor binding | + | 0.7327 | 73.27% |
| Glucocorticoid receptor binding | + | 0.8713 | 87.13% |
| Aromatase binding | + | 0.8812 | 88.12% |
| PPAR gamma | + | 0.5826 | 58.26% |
| Honey bee toxicity | - | 0.9541 | 95.41% |
| Biodegradation | - | 0.9250 | 92.50% |
| Crustacea aquatic toxicity | + | 0.8100 | 81.00% |
| Fish aquatic toxicity | - | 0.7539 | 75.39% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
31622.8 nM 28183.8 nM 5011.9 nM 7943.3 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
8912.5 nM 5623.4 nM 11220.2 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL1867 | P08913 | Alpha-2a adrenergic receptor |
2540 nM |
Ki |
PMID: 14643338
|
| CHEMBL1942 | P18089 | Alpha-2b adrenergic receptor |
1130 nM |
Ki |
PMID: 14643338
|
| CHEMBL1916 | P18825 | Alpha-2c adrenergic receptor |
810 nM |
Ki |
PMID: 14643338
|
| CHEMBL2828 | P48730 | Casein kinase I delta |
1500 nM |
IC50 |
PMID: 17850214
|
| CHEMBL3356 | P05177 | Cytochrome P450 1A2 |
398.11 nM |
AC50 |
via CMAUP
|
| CHEMBL289 | P10635 | Cytochrome P450 2D6 |
7943.28 nM |
AC50 |
via CMAUP
|
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
10000 nM 15848.9 nM 15848.9 nM 10000 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL5543 | Q9Y463 | Dual specificity tyrosine-phosphorylation-regulated kinase 1B |
28 nM 180 nM 166 nM |
IC50 IC50 IC50 |
via Super-PRED
PMID: 26896709 PMID: 25738750 |
| CHEMBL4224 | P49759 | Dual specificty protein kinase CLK1 |
26 nM 220 nM 26 nM |
IC50 IC50 IC50 |
via Super-PRED
PMID: 26896709 PMID: 23237976 |
| CHEMBL2292 | Q13627 | Dual-specificity tyrosine-phosphorylation regulated kinase 1A |
60 nM 8.81 nM 80 nM 30 nM 80 nM 60 nM 85 nM 80 nM 33 nM 130 nM 33 nM 80 nM |
IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 |
PMID: 25248682
via Super-PRED PMID: 17850214 PMID: 22335895 PMID: 22770529 PMID: 22998443 PMID: 22998443 PMID: 23237976 PMID: 25738750 PMID: 26896709 PMID: 24188002 PMID: 26048785 |
| CHEMBL4376 | Q92630 | Dual-specificity tyrosine-phosphorylation regulated kinase 2 |
2000 nM 120 nM 900 nM 900 nM 120 nM 690 nM |
IC50 IC50 IC50 IC50 IC50 IC50 |
PMID: 25738750
via Super-PRED PMID: 23237976 PMID: 17850214 PMID: 22998443 PMID: 22335895 |
| CHEMBL4575 | O43781 | Dual-specificity tyrosine-phosphorylation regulated kinase 3 |
800 nM 800 nM 210 nM |
IC50 IC50 IC50 |
PMID: 23237976
PMID: 17850214 via Super-PRED |
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
15848.9 nM 12589.3 nM 25118.9 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha |
6309.6 nM 6309.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
12589.3 nM 28183.8 nM 28183.8 nM 14125.4 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL1951 | P21397 | Monoamine oxidase A |
17 nM 16.9 nM 5 nM |
Ki Ki Ki |
PMID: 21726069
PMID: 21183355 via Super-PRED |
| CHEMBL3923 | Q9Y2I1 | Nischarin |
22 nM 13800 nM 22 nM |
Ki Ki Ki |
PMID: 14643338
PMID: 14643338 via Super-PRED |
| CHEMBL222 | P23975 | Norepinephrine transporter |
3260 nM |
Ki |
PMID: 14643338
|
| CHEMBL1075163 | Q8TF76 | Serine/threonine-protein kinase haspin |
590 nM 590 nM |
IC50 IC50 |
PMID: 22335895
via Super-PRED |
| CHEMBL5407 | Q86V86 | Serine/threonine-protein kinase PIM3 |
4300 nM |
IC50 |
PMID: 17850214
|
| CHEMBL225 | P28335 | Serotonin 2c (5-HT2c) receptor |
9340 nM |
Ki |
PMID: 14643338
|
| CHEMBL3371 | P50406 | Serotonin 6 (5-HT6) receptor |
1480 nM |
Ki |
PMID: 14643338
|
| CHEMBL3155 | P34969 | Serotonin 7 (5-HT7) receptor |
5500 nM |
Ki |
PMID: 14643338
|
| CHEMBL1293232 | Q16637 | Survival motor neuron protein |
3548.1 nM 3162.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 93.48% | 94.00% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.36% | 96.09% |
| CHEMBL1907 | P15144 | Aminopeptidase N | 92.95% | 93.31% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 92.31% | 95.56% |
| CHEMBL1868 | P17948 | Vascular endothelial growth factor receptor 1 | 92.12% | 96.47% |
| CHEMBL3192 | Q9BY41 | Histone deacetylase 8 | 91.33% | 93.99% |
| CHEMBL4481 | P35228 | Nitric oxide synthase, inducible | 90.05% | 94.80% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 88.65% | 94.45% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 86.80% | 91.11% |
| CHEMBL3714130 | P46095 | G-protein coupled receptor 6 | 86.61% | 97.36% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 85.60% | 90.00% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 84.73% | 96.00% |
| CHEMBL2424504 | P29375 | Lysine-specific demethylase 5A | 83.90% | 99.23% |
| CHEMBL4145 | Q9UKV0 | Histone deacetylase 9 | 83.82% | 85.49% |
| CHEMBL255 | P29275 | Adenosine A2b receptor | 83.77% | 98.59% |
| CHEMBL1781 | P11387 | DNA topoisomerase I | 83.64% | 97.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 83.52% | 99.15% |
| CHEMBL2095172 | P14867 | GABA-A receptor; alpha-1/beta-2/gamma-2 | 83.46% | 92.67% |
| CHEMBL2535 | P11166 | Glucose transporter | 82.96% | 98.75% |
| CHEMBL2146302 | O94925 | Glutaminase kidney isoform, mitochondrial | 82.63% | 100.00% |
| CHEMBL5409 | Q8TDU6 | G-protein coupled bile acid receptor 1 | 82.41% | 93.65% |
| CHEMBL2335 | P42785 | Lysosomal Pro-X carboxypeptidase | 82.15% | 100.00% |
| CHEMBL1937 | Q92769 | Histone deacetylase 2 | 82.07% | 94.75% |
| CHEMBL4016 | P42262 | Glutamate receptor ionotropic, AMPA 2 | 80.77% | 86.92% |
| CHEMBL2378 | P30307 | Dual specificity phosphatase Cdc25C | 80.57% | 96.67% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.
| PubChem | 5280953 |
| NPASS | NPC232727 |
| ChEMBL | CHEMBL269538 |
| LOTUS | LTS0131294 |
| wikiData | Q128381 |