2-Methyltryptoline

Details

• Internal ID: b3aaf5a7-a6ce-4665-a4b4-3c5a6381479d
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: 2-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
• SMILES (Canonical): CN1CCC2=C(C1)NC3=CC=CC=C23
• SMILES (Isomeric): CN1CCC2=C(C1)NC3=CC=CC=C23
• InChI: InChI=1S/C12H14N2/c1-14-7-6-10-9-4-2-3-5-11(9)13-12(10)8-14/h2-5,13H,6-8H2,1H3
• InChI Key: JOFKCNJIUXPJAC-UHFFFAOYSA-N
• Popularity: 51 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25 g/mol
• Exact Mass: 186.115698455 g/mol
• Topological Polar Surface Area (TPSA): 19.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.16
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 13100-00-0
• 2-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
• 2-Methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 2-Methyl-1,2,3,4-tetrahydro-beta-carboline
• CHEMBL69618
• 1,2,3,4-Tetrahydro-2-methyl-b-carboline
• 1H-Pyrido[3,4-b]indole, 2,3,4,9-tetrahydro-2-methyl-
• NSC683435
• 2-Methyl-2,3,4,9-tetrahydro-1H-b-carboline
• 2-Methyl-2,3,4,9-tetrahydro-1H-beta-carboline
• 2-Methyl-9H-1,2,3,4-tetrahydropyrido(3,4-b) indole
• Alkaloid GPZ-2
• Oprea1_539196
• MLS001049128
• 2-Methyltetrahydro-b-carboline
• SCHEMBL1055807
• n-methyltetrahydro-beta-carboline
• 2-Methyltetrahydro-beta-carboline
• DTXSID40156838
• TQP1342
• CHEBI:185749
• HMS2268E23
• BDBM50018545
• AKOS006320934
• NSC-683435
• NCGC00246229-01
• NCI60_029908
• PD166857
• SMR000386955
• 2-Methyl-1,2,3,4-tetrahydro-.beta.-carboline
• 2-Methyl-2,3,4,9-tetrahydro-1H-.beta.-carboline
• 2-Methyl-2,3,4,9-tetrahydro-1H-beta-carboline #
• 2,3,4,9-Tetrahydro-2-methyl-1H-Pyrido[3,4-b]indole
• 2-METHYL-1H,2H,3H,4H,9H-PYRIDO[3,4-B]INDOLE
• F1905-8574
• 2,3,4,9-Tetrahydro-2-methyl-1H-pyrido[3,4-b]indole, 9CI
• InChI=1/C12H14N2/c1-14-7-6-10-9-4-2-3-5-11(9)13-12(10)8-14/h2-5,13H,6-8H2,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.9451	94.51%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.7163	71.63%
OATP2B1 inhibitior	-	0.8644	86.44%
OATP1B1 inhibitior	+	0.9303	93.03%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.8157	81.57%
P-glycoprotein inhibitior	-	0.9908	99.08%
P-glycoprotein substrate	-	0.7483	74.83%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	+	0.8117	81.17%
CYP2D6 substrate	+	0.7154	71.54%
CYP3A4 inhibition	-	0.7783	77.83%
CYP2C9 inhibition	-	0.8087	80.87%
CYP2C19 inhibition	-	0.7478	74.78%
CYP2D6 inhibition	-	0.7347	73.47%
CYP1A2 inhibition	+	0.8076	80.76%
CYP2C8 inhibition	-	0.9391	93.91%
CYP inhibitory promiscuity	-	0.7804	78.04%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7936	79.36%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.6289	62.89%
Skin irritation	-	0.6163	61.63%
Skin corrosion	-	0.8921	89.21%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3697	36.97%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.7198	71.98%
skin sensitisation	-	0.9156	91.56%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7656	76.56%
Acute Oral Toxicity (c)	III	0.6125	61.25%
Estrogen receptor binding	-	0.7308	73.08%
Androgen receptor binding	-	0.6176	61.76%
Thyroid receptor binding	-	0.8299	82.99%
Glucocorticoid receptor binding	-	0.8242	82.42%
Aromatase binding	-	0.7412	74.12%
PPAR gamma	-	0.8307	83.07%
Honey bee toxicity	-	0.9555	95.55%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7500	75.00%
Fish aquatic toxicity	+	0.8505	85.05%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.16%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.96%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.96%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.58%	93.40%
CHEMBL2535	P11166	Glucose transporter	89.64%	98.75%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	88.61%	96.42%
CHEMBL1951	P21397	Monoamine oxidase A	88.46%	91.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.58%	93.99%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.24%	88.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.75%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.53%	94.45%
CHEMBL2056	P21728	Dopamine D1 receptor	84.84%	91.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.83%	93.65%
CHEMBL4208	P20618	Proteasome component C5	83.97%	90.00%
CHEMBL255	P29275	Adenosine A2b receptor	83.47%	98.59%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	80.61%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.38%	97.25%

Plants that contains it

• Arundo donax
• Cyathobasis fruticulosa
• Papaver rhoeas
• Phalaris aquatica
• Phalaris arundinacea
• Phalaris coerulescens
• Sanguisorba officinalis

Cross-Links

• PubChem: 121896
• NPASS: NPC198988
• ChEMBL: CHEMBL69618
• LOTUS: LTS0032864
• wikiData: Q83024951