3-Indoleacetonitrile

Details

• Internal ID: 5837ce30-fab3-421a-aef9-ac06142de081
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
• IUPAC Name: 2-(1H-indol-3-yl)acetonitrile
• SMILES (Canonical): C1=CC=C2C(=C1)C(=CN2)CC#N
• SMILES (Isomeric): C1=CC=C2C(=C1)C(=CN2)CC#N
• InChI: InChI=1S/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
• InChI Key: DMCPFOBLJMLSNX-UHFFFAOYSA-N
• Popularity: 708 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₈N₂
• Molecular Weight: 156.18 g/mol
• Exact Mass: 156.068748264 g/mol
• Topological Polar Surface Area (TPSA): 39.60 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.23
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 771-51-7
• Indole-3-acetonitrile
• 2-(1H-indol-3-yl)acetonitrile
• 3-Indolylacetonitrile
• 1H-Indole-3-acetonitrile
• 3-(Cyanomethyl)indole
• Indolylacetonitrile
• Indoleacetonitrile
• Indolylacetonitril
• 3-Indolacetonitrile
• Acetonitrile, 3-indolyl-
• 1H-Indol-3-ylacetonitrile
• Indol-3-ylacetonitrile
• (3-Indolyl)acetonitrile
• USAF CB-29
• (indol-3-yl)acetonitrile
• 3-Cyanomethyl-1H-indole
• (1H-indol-3-yl)-acetonitrile
• NSC 523272
• CCRIS 5807
• Indolyl-3-acetonitrile
• EINECS 212-232-1
• AG97OFW8JW
• (Indole-3-yl)acetonitrile
• BRN 0125488
• (1H-Indol-3-yl)acetonitrile
• AI3-50105
• CHEMBL1812654
• CHEBI:17566
• NSC-523272
• 5-22-03-00074 (Beilstein Handbook Reference)
• IAN
• 3-cyanomethylindole
• b-Indoleacetonitrile
• MFCD00005628
• beta-Indoleacetonitrile
• 3-indolyl-Acetonitrile
• indole-3-ylacetonitrile
• .beta.-Indoleacetonitrile
• UNII-AG97OFW8JW
• beta-indole-3-acetonitrile
• bmse000488
• 1H-indole-3-ylacetonitrile
• 3-Indoleacetonitrile, 98%
• 1H-Indol-3-ylacetonitrile #
• BIDD:GT0196
• SCHEMBL149254
• WLN: T56 BMJ D1CN
• 2(1H-indol-3-yl)acetonitrile
• AMY871
• DTXSID5061118
• DMCPFOBLJMLSNX-UHFFFAOYSA-
• 2-(1H-indol-3-yl)ethanenitrile
• 2-(1H-indol-3-yl)-acetonitrile
• GLXC-26570
• HY-Y0136
• BDBM50350241
• NSC523272
• s6043
• STK802120
• AKOS000120379
• CS-W008768
• MB00159
• PS-3276
• AC-10572
• PD124092
• I0024
• EN300-20368
• 3-Indoleacetonitrile, purum, >=96.0% (GC)
• C02938
• I-5650
• A838975
• BRD-K65452854-001-01-5
• Q27102461
• Z104477894
• 71C17B3A-CA19-4822-A4E7-D424F7074B4C
• InChI=1/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2
• 3BO

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9971	99.71%
Caco-2	+	0.8124	81.24%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Lysosomes	0.4750	47.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9421	94.21%
OATP1B3 inhibitior	+	0.9535	95.35%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7825	78.25%
P-glycoprotein inhibitior	-	0.9847	98.47%
P-glycoprotein substrate	-	0.9386	93.86%
CYP3A4 substrate	-	0.5633	56.33%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	+	0.4183	41.83%
CYP3A4 inhibition	-	0.6385	63.85%
CYP2C9 inhibition	+	0.5787	57.87%
CYP2C19 inhibition	+	0.6862	68.62%
CYP2D6 inhibition	+	0.6579	65.79%
CYP1A2 inhibition	+	0.8200	82.00%
CYP2C8 inhibition	-	0.8259	82.59%
CYP inhibitory promiscuity	+	0.6515	65.15%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.7156	71.56%
Eye corrosion	-	0.9638	96.38%
Eye irritation	+	0.9818	98.18%
Skin irritation	-	0.5509	55.09%
Skin corrosion	-	0.8919	89.19%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4620	46.20%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.7770	77.70%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5611	56.11%
Acute Oral Toxicity (c)	III	0.7291	72.91%
Estrogen receptor binding	-	0.7184	71.84%
Androgen receptor binding	-	0.8439	84.39%
Thyroid receptor binding	-	0.7842	78.42%
Glucocorticoid receptor binding	-	0.6813	68.13%
Aromatase binding	-	0.5052	50.52%
PPAR gamma	-	0.5575	55.75%
Honey bee toxicity	-	0.6798	67.98%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	-	0.4341	43.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.98%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.01%	94.62%
CHEMBL2581	P07339	Cathepsin D	89.10%	98.95%
CHEMBL2535	P11166	Glucose transporter	88.13%	98.75%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	86.73%	83.10%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.52%	93.99%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	86.48%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.06%	95.56%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.87%	88.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.53%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.55%	89.62%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.81%	94.23%
CHEMBL2996	Q05655	Protein kinase C delta	81.98%	97.79%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	81.75%	96.42%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.66%	92.62%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.84%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.18%	91.71%
CHEMBL255	P29275	Adenosine A2b receptor	80.06%	98.59%

Plants that contains it

• Arabidopsis thaliana
• Brassica juncea
• Brassica oleracea
• Eutrema halophilum
• Impatiens balsamina
• Isatis tinctoria
• Rorippa indica

Cross-Links

• PubChem: 351795
• NPASS: NPC279081
• LOTUS: LTS0100514
• wikiData: Q27102461