(2S)-2-[3-(cyanomethyl)-4-methoxy-1H-indol-7-yl]-2-(4-methoxy-1H-indol-3-yl)acetonitrile

Details

• Internal ID: 4ef83a19-e99f-4001-8ac1-cfd1769f7e37
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
• IUPAC Name: (2S)-2-[3-(cyanomethyl)-4-methoxy-1H-indol-7-yl]-2-(4-methoxy-1H-indol-3-yl)acetonitrile
• SMILES (Canonical): COC1=C2C(=CNC2=C(C=C1)C(C#N)C3=CNC4=C3C(=CC=C4)OC)CC#N
• SMILES (Isomeric): COC1=C2C(=CNC2=C(C=C1)[C@@H](C#N)C3=CNC4=C3C(=CC=C4)OC)CC#N
• InChI: InChI=1S/C22H18N4O2/c1-27-18-5-3-4-17-21(18)16(12-25-17)15(10-24)14-6-7-19(28-2)20-13(8-9-23)11-26-22(14)20/h3-7,11-12,15,25-26H,8H2,1-2H3/t15-/m1/s1
• InChI Key: PDIDHZDRZQKFOX-OAHLLOKOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₈N₄O₂
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.14297583 g/mol
• Topological Polar Surface Area (TPSA): 97.60 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.5751	57.51%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8341	83.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9004	90.04%
OATP1B3 inhibitior	+	0.9383	93.83%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.8194	81.94%
P-glycoprotein inhibitior	+	0.8115	81.15%
P-glycoprotein substrate	+	0.5670	56.70%
CYP3A4 substrate	+	0.6392	63.92%
CYP2C9 substrate	-	0.8100	81.00%
CYP2D6 substrate	+	0.4580	45.80%
CYP3A4 inhibition	+	0.8514	85.14%
CYP2C9 inhibition	-	0.5278	52.78%
CYP2C19 inhibition	+	0.6116	61.16%
CYP2D6 inhibition	+	0.7470	74.70%
CYP1A2 inhibition	+	0.8426	84.26%
CYP2C8 inhibition	+	0.6123	61.23%
CYP inhibitory promiscuity	+	0.9204	92.04%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.4857	48.57%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.8705	87.05%
Skin irritation	-	0.8586	85.86%
Skin corrosion	-	0.9560	95.60%
Ames mutagenesis	+	0.5463	54.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.8828	88.28%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9078	90.78%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5784	57.84%
Acute Oral Toxicity (c)	III	0.5953	59.53%
Estrogen receptor binding	+	0.9070	90.70%
Androgen receptor binding	+	0.7371	73.71%
Thyroid receptor binding	+	0.8607	86.07%
Glucocorticoid receptor binding	+	0.8827	88.27%
Aromatase binding	+	0.7366	73.66%
PPAR gamma	+	0.6731	67.31%
Honey bee toxicity	-	0.6339	63.39%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	-	0.6085	60.85%

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	98.27%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.33%	98.95%
CHEMBL213	P08588	Beta-1 adrenergic receptor	95.71%	95.56%
CHEMBL2535	P11166	Glucose transporter	95.32%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	95.07%	90.20%
CHEMBL4179	P45984	c-Jun N-terminal kinase 2	94.01%	90.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.59%	89.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.38%	93.99%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.17%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.44%	86.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.41%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.26%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.63%	95.56%
CHEMBL1907	P15144	Aminopeptidase N	86.84%	93.31%
CHEMBL1937	Q92769	Histone deacetylase 2	85.97%	94.75%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.65%	85.30%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.55%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.34%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.07%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.04%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.01%	94.45%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 70690688
• NPASS: NPC170114
• ChEMBL: CHEMBL2063174
• LOTUS: LTS0157124
• wikiData: Q105206517