(1S)-2-methyl-1-(2-methylprop-1-enyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole

Details

• Internal ID: ebbd022c-d68c-4fb6-96fa-c91823e668aa
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (1S)-2-methyl-1-(2-methylprop-1-enyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole
• SMILES (Canonical): CC(=CC1C2=C(CCN1C)C3=CC=CC=C3N2)C
• SMILES (Isomeric): CC(=C[C@H]1C2=C(CCN1C)C3=CC=CC=C3N2)C
• InChI: InChI=1S/C16H20N2/c1-11(2)10-15-16-13(8-9-18(15)3)12-6-4-5-7-14(12)17-16/h4-7,10,15,17H,8-9H2,1-3H3/t15-/m0/s1
• InChI Key: RCNFEGDNDAQFRX-HNNXBMFYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₀N₂
• Molecular Weight: 240.34 g/mol
• Exact Mass: 240.162648646 g/mol
• Topological Polar Surface Area (TPSA): 19.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.66
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9882	98.82%
Caco-2	+	0.9427	94.27%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4926	49.26%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.9204	92.04%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	-	0.4723	47.23%
P-glycoprotein inhibitior	-	0.9479	94.79%
P-glycoprotein substrate	-	0.6026	60.26%
CYP3A4 substrate	+	0.5881	58.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6742	67.42%
CYP3A4 inhibition	+	0.5346	53.46%
CYP2C9 inhibition	-	0.7639	76.39%
CYP2C19 inhibition	-	0.7456	74.56%
CYP2D6 inhibition	+	0.6383	63.83%
CYP1A2 inhibition	+	0.7419	74.19%
CYP2C8 inhibition	-	0.9017	90.17%
CYP inhibitory promiscuity	+	0.5341	53.41%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7230	72.30%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9361	93.61%
Skin irritation	-	0.6793	67.93%
Skin corrosion	-	0.8777	87.77%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9042	90.42%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.5824	58.24%
skin sensitisation	-	0.8453	84.53%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8553	85.53%
Acute Oral Toxicity (c)	III	0.5834	58.34%
Estrogen receptor binding	+	0.5945	59.45%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6146	61.46%
Glucocorticoid receptor binding	+	0.6218	62.18%
Aromatase binding	+	0.5753	57.53%
PPAR gamma	-	0.5183	51.83%
Honey bee toxicity	-	0.8868	88.68%
Biodegradation	-	1.0000	100.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9500	95.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.52%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.39%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.92%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.18%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	91.93%	91.49%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.30%	93.40%
CHEMBL3310	Q96DB2	Histone deacetylase 11	85.85%	88.56%
CHEMBL255	P29275	Adenosine A2b receptor	84.93%	98.59%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.86%	89.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.40%	96.39%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.34%	93.99%
CHEMBL2535	P11166	Glucose transporter	80.67%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.14%	95.89%

Plants that contains it

• Flindersia fournieri
• Spermacoce verticillata

Cross-Links

• PubChem: 134860448
• LOTUS: LTS0172333
• wikiData: Q105233818