Tetrahydroharmol

Details

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Internal ID ee751990-2cf5-4691-b815-0471f531f6cc
Taxonomy Alkaloids and derivatives > Harmala alkaloids
IUPAC Name 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-ol
SMILES (Canonical) CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)O
SMILES (Isomeric) CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)O
InChI InChI=1S/C12H14N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6-7,13-15H,4-5H2,1H3
InChI Key AZTMWIPCEFFOJD-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C12H14N2O
Molecular Weight 202.25 g/mol
Exact Mass 202.110613074 g/mol
Topological Polar Surface Area (TPSA) 48.00 Ų
XlogP 1.50
Atomic LogP (AlogP) 2.08
H-Bond Acceptor 2
H-Bond Donor 3
Rotatable Bonds 0

Synonyms

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Harmalol, dihydro-
DHR7GV467K
Tetrahydroharmol hydrochloride
17952-75-9
UNII-DHR7GV467K
1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-ol
1-Methyl-1H,2H,3H,4H,9H-pyrido(3,4-b)indol-7-ol
2,3,4,9-Tetrahydro-1-methyl-1H-pyrido(3,4-b)indol-7-ol
1H-Pyrido(3,4-b)indol-7-ol, 2,3,4,9-tetrahydro-1-methyl-
Tetrahydroharmalol hydrochloride
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Tetrahydroharmol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9905 99.05%
Caco-2 - 0.5653 56.53%
Blood Brain Barrier + 0.7129 71.29%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.4245 42.45%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8720 87.20%
OATP1B3 inhibitior + 0.9472 94.72%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior + 0.5750 57.50%
BSEP inhibitior - 0.8762 87.62%
P-glycoprotein inhibitior - 0.9584 95.84%
P-glycoprotein substrate - 0.5752 57.52%
CYP3A4 substrate - 0.5192 51.92%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.4329 43.29%
CYP3A4 inhibition - 0.9159 91.59%
CYP2C9 inhibition - 0.9440 94.40%
CYP2C19 inhibition - 0.7714 77.14%
CYP2D6 inhibition + 0.7669 76.69%
CYP1A2 inhibition + 0.6746 67.46%
CYP2C8 inhibition - 0.6322 63.22%
CYP inhibitory promiscuity - 0.7498 74.98%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6678 66.78%
Eye corrosion - 0.9875 98.75%
Eye irritation - 0.9220 92.20%
Skin irritation - 0.7378 73.78%
Skin corrosion - 0.8949 89.49%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5471 54.71%
Micronuclear + 0.5800 58.00%
Hepatotoxicity - 0.5250 52.50%
skin sensitisation - 0.8335 83.35%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.9375 93.75%
Nephrotoxicity - 0.8438 84.38%
Acute Oral Toxicity (c) III 0.5843 58.43%
Estrogen receptor binding - 0.5290 52.90%
Androgen receptor binding + 0.6988 69.88%
Thyroid receptor binding + 0.5691 56.91%
Glucocorticoid receptor binding - 0.6498 64.98%
Aromatase binding - 0.4827 48.27%
PPAR gamma + 0.6509 65.09%
Honey bee toxicity - 0.9497 94.97%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity - 0.8025 80.25%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL1951 P21397 Monoamine oxidase A 98.56% 91.49%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.31% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.24% 94.45%
CHEMBL242 Q92731 Estrogen receptor beta 91.95% 98.35%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.60% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.35% 97.09%
CHEMBL206 P03372 Estrogen receptor alpha 90.46% 97.64%
CHEMBL2581 P07339 Cathepsin D 89.55% 98.95%
CHEMBL2535 P11166 Glucose transporter 87.96% 98.75%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 87.37% 91.79%
CHEMBL213 P08588 Beta-1 adrenergic receptor 87.08% 95.56%
CHEMBL241 Q14432 Phosphodiesterase 3A 86.52% 92.94%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 86.07% 91.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.65% 95.56%
CHEMBL3155 P34969 Serotonin 7 (5-HT7) receptor 83.91% 90.71%
CHEMBL3438 Q05513 Protein kinase C zeta 82.71% 88.48%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 82.69% 93.40%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.79% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.76% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.74% 89.00%
CHEMBL1907594 P30926 Neuronal acetylcholine receptor; alpha3/beta4 81.12% 97.23%
CHEMBL4208 P20618 Proteasome component C5 80.35% 90.00%

Plants that contains it

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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.
Elaeagnus angustifolia
Peganum harmala
Shepherdia argentea

Cross-Links

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PubChem 368982
NPASS NPC107975
LOTUS LTS0230248
wikiData Q15427887