6-Methoxy-1-methyl-9H-pyrido(3,4-b)indole

Details

• Internal ID: 1710622b-c029-4284-946a-2f618b0ff2b3
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 6-methoxy-1-methyl-9H-pyrido[3,4-b]indole
• InChI: InChI=1S/C13H12N2O/c1-8-13-10(5-6-14-8)11-7-9(16-2)3-4-12(11)15-13/h3-7,15H,1-2H3
• InChI Key: XYYVPBBISSKKQB-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• 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

Synonyms

• 3589-72-8
• 6-methoxy-1-methyl-9H-pyrido[3,4-b]indole
• Coharmine
• 6-Methoxy-1-methyl-9H-pyrido(3,4-b)indole
• 9H-Pyrido(3,4-b)indole, 6-methoxy-1-methyl-
• 48GQI7H930
• NSC-92536
• 9H-Pyrido[3,4-b]indole, 6-methoxy-1-methyl-
• RefChem:1074030
• 986-751-3
• 6-Methoxyharmane
• Isoharmine
• CHEMBL278193
• NSC 92536
• BRN 0178687
• 6-Methoxy Harman
• NSC92536
• Oprea1_024115
• 4-23-00-02701 (Beilstein Handbook Reference)
• UNII-48GQI7H930
• SCHEMBL5035404
• DTXSID40189449
• XYYVPBBISSKKQB-UHFFFAOYSA-N
• DAA58972
• BDBM50132122
• MFCD01544241
• AKOS037651093
• 6-Methoxy-1-methyl-9H-beta-carboline
• .beta.-Carboline, 6-methoxy-1-methyl-
• 6-Methoxy-1-methyl-9H-beta-carboline #
• CS-15875
• DS-009456
• CS-0062557
• D72284
• F603471
• Q15426262

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.8976	89.76%
Blood Brain Barrier	+	0.7629	76.29%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7977	79.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9508	95.08%
OATP1B3 inhibitior	+	0.9514	95.14%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5767	57.67%
P-glycoprotein inhibitior	-	0.9312	93.12%
P-glycoprotein substrate	-	0.6360	63.60%
CYP3A4 substrate	-	0.5286	52.86%
CYP2C9 substrate	-	0.7825	78.25%
CYP2D6 substrate	-	0.6664	66.64%
CYP3A4 inhibition	+	0.7789	77.89%
CYP2C9 inhibition	-	0.9079	90.79%
CYP2C19 inhibition	-	0.8263	82.63%
CYP2D6 inhibition	+	0.8987	89.87%
CYP1A2 inhibition	+	0.9647	96.47%
CYP2C8 inhibition	+	0.4575	45.75%
CYP inhibitory promiscuity	+	0.7086	70.86%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9823	98.23%
Carcinogenicity (trinary)	Non-required	0.5313	53.13%
Eye corrosion	-	0.9888	98.88%
Eye irritation	+	0.8181	81.81%
Skin irritation	-	0.7993	79.93%
Skin corrosion	-	0.9568	95.68%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4455	44.55%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5513	55.13%
skin sensitisation	-	0.9240	92.40%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.8301	83.01%
Acute Oral Toxicity (c)	III	0.6350	63.50%
Estrogen receptor binding	+	0.9234	92.34%
Androgen receptor binding	+	0.7794	77.94%
Thyroid receptor binding	+	0.6517	65.17%
Glucocorticoid receptor binding	+	0.7401	74.01%
Aromatase binding	+	0.8493	84.93%
PPAR gamma	-	0.5169	51.69%
Honey bee toxicity	-	0.9540	95.40%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.8000	80.00%
Fish aquatic toxicity	-	0.7496	74.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.41%	91.49%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	97.30%	93.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.83%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.42%	94.00%
CHEMBL1907	P15144	Aminopeptidase N	93.12%	93.31%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	92.31%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.20%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.01%	93.99%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.05%	91.11%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	89.19%	85.49%
CHEMBL255	P29275	Adenosine A2b receptor	86.94%	98.59%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.25%	92.94%
CHEMBL2535	P11166	Glucose transporter	86.11%	98.75%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.33%	93.65%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.13%	96.00%
CHEMBL4208	P20618	Proteasome component C5	84.88%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.56%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.43%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.42%	85.14%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.95%	85.30%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.76%	92.67%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.57%	93.10%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.56%	99.15%
CHEMBL2424504	P29375	Lysine-specific demethylase 5A	83.33%	99.23%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.09%	91.71%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.96%	100.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.86%	96.00%
CHEMBL5443	O00311	Cell division cycle 7-related protein kinase	82.80%	96.11%
CHEMBL1781	P11387	DNA topoisomerase I	81.30%	97.00%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.26%	85.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.21%	94.75%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.16%	94.80%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.09%	96.67%

Plants that contains it

• Peganum harmala

Cross-Links

• PubChem: 5376026
• LOTUS: LTS0210159
• wikiData: Q15426262