6-Methoxyharmalan

Details

• Internal ID: 98e1fbdf-8de4-42bd-9f68-a481e679719e
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 6-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
• SMILES (Canonical): CC1=NCCC2=C1NC3=C2C=C(C=C3)OC
• SMILES (Isomeric): CC1=NCCC2=C1NC3=C2C=C(C=C3)OC
• InChI: InChI=1S/C13H14N2O/c1-8-13-10(5-6-14-8)11-7-9(16-2)3-4-12(11)15-13/h3-4,7,15H,5-6H2,1-2H3
• InChI Key: HMBHRMFLDKKSCT-UHFFFAOYSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄N₂O
• Molecular Weight: 214.26 g/mol
• Exact Mass: 214.110613074 g/mol
• Topological Polar Surface Area (TPSA): 37.40 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 3589-73-9
• 6-Methoxyharmalane
• 10-Methoxyharmalan
• Methoxy-6-harmalan
• 6-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole
• 6-Methoxy-Harmalan
• 43F45VJV8C
• 6-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
• CHEMBL338115
• 4,9-Dihydro-6-methoxy-1-methyl-3H-pyrido(3,4-b)indole
• 6-Methoxy-1-methyl-4,9-dihydro-3H-pyrido(3,4-b)indole
• UNII-43F45VJV8C
• 1-Methyl-6-methoxy-dihydro-beta-carboline
• Prestwick_324
• NoName_1047
• Prestwick0_000621
• Prestwick1_000621
• Prestwick2_000621
• Prestwick3_000621
• 1-methyl-6-methoxy-3,4-dihydro-2-carboline
• 6-Methoxy-1-methyl-4,9-dihydro-3H-pyrido(3,4-b)indole monohydrochloride
• Oprea1_335320
• BSPBio_000582
• MLS002153914
• 6-Methoxyharmalan, crystalline
• SPBio_002801
• BPBio1_000642
• SCHEMBL3877767
• 3,4-DIHYDROMETHOXYHARMAN
• CHEBI:92962
• 10-METHOXYHARMALAN [MI]
• 6-METHOXY-1-METHYL-3H,4H,9H-PYRIDO[3,4-B]INDOLE
• DTXSID10901872
• DTXSID80957306
• HMBHRMFLDKKSCT-UHFFFAOYSA-N
• PIRYBCJVLMHZOK-UHFFFAOYSA-N
• HMS1569N04
• HMS2096N04
• HMS2233C16
• HMS3370E16
• BDBM50132104
• 3H-Pyrido(3,4-b)indole, 4,9-dihydro-6-methoxy-1-methyl-, monohydrochloride
• AKOS037646003
• NCGC00016633-01
• NCGC00016633-02
• AS-65610
• SMR001233263
• CAS-3589-73-9
• Ethyl3-(naphthalen-8-yl)-3-oxopropanoate
• FT-0634918
• 6-Methoxy-1-methyl-3,4-dihydro-.beta.-carboline
• A823026
• SR-01000841225
• 1-METHYL-6-METHOXY-DIHYDRO-.BETA.-CARBOLINE
• 6-Methoxy-1-methyl-4,9-dihydro-3H-beta-carboline
• SR-01000841225-2
• BRD-K54906270-001-03-5
• Q27164697
• Q27258644
• 3H-Pyrido(3,4-b)indole, 4,9-dihydro-6-methoxy-1-methyl-
• 3H-Pyrido(3,4-b)indole, 4,9-dihydro-6-methoxy-1-methyl-, monohydrochloride (Salt/Mix)
• 6-Methoxy-1-methyl-4,9-dihydro-3H-pyrido(3,4-b)indole monohydrochloride (Salt/Mix)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9953	99.53%
Caco-2	-	0.8205	82.05%
Blood Brain Barrier	+	0.8629	86.29%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6789	67.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	-	0.4642	46.42%
P-glycoprotein inhibitior	-	0.9608	96.08%
P-glycoprotein substrate	-	0.7511	75.11%
CYP3A4 substrate	+	0.5559	55.59%
CYP2C9 substrate	+	0.5701	57.01%
CYP2D6 substrate	-	0.7639	76.39%
CYP3A4 inhibition	+	0.6989	69.89%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9146	91.46%
CYP2C8 inhibition	-	0.6889	68.89%
CYP inhibitory promiscuity	-	0.5555	55.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6915	69.15%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.7398	73.98%
Skin irritation	-	0.7210	72.10%
Skin corrosion	-	0.8922	89.22%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5069	50.69%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8659	86.59%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8491	84.91%
Acute Oral Toxicity (c)	III	0.5631	56.31%
Estrogen receptor binding	+	0.7666	76.66%
Androgen receptor binding	+	0.6902	69.02%
Thyroid receptor binding	+	0.6116	61.16%
Glucocorticoid receptor binding	+	0.6254	62.54%
Aromatase binding	+	0.5649	56.49%
PPAR gamma	+	0.6688	66.88%
Honey bee toxicity	-	0.9334	93.34%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7900	79.00%
Fish aquatic toxicity	-	0.6144	61.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4145	Q9UKV0	Histone deacetylase 9	96.10%	85.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.94%	93.99%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.90%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.21%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.73%	96.09%
CHEMBL2535	P11166	Glucose transporter	92.58%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.72%	94.00%
CHEMBL240	Q12809	HERG	91.48%	89.76%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	91.22%	91.71%
CHEMBL1907	P15144	Aminopeptidase N	88.49%	93.31%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.94%	92.62%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	87.63%	96.47%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.41%	80.96%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.65%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.58%	97.09%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	86.16%	95.70%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.31%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.64%	98.95%
CHEMBL5747	Q92793	CREB-binding protein	84.48%	95.12%
CHEMBL4302	P08183	P-glycoprotein 1	84.25%	92.98%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.12%	92.94%
CHEMBL5443	O00311	Cell division cycle 7-related protein kinase	83.61%	96.11%
CHEMBL1871	P10275	Androgen Receptor	83.49%	96.43%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	83.08%	95.48%
CHEMBL4208	P20618	Proteasome component C5	82.80%	90.00%
CHEMBL3902	P09211	Glutathione S-transferase Pi	82.60%	93.81%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.80%	96.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.46%	93.40%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	80.64%	90.71%
CHEMBL2056	P21728	Dopamine D1 receptor	80.63%	91.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 417052
• LOTUS: LTS0241362
• wikiData: Q27258644