2-[(3S)-3-hydroxy-4-methoxy-2-oxo-1H-indol-3-yl]acetonitrile

Details

• Internal ID: 5e4d4b57-e375-4e9e-b0f1-180576276237
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolines
• IUPAC Name: 2-[(3S)-3-hydroxy-4-methoxy-2-oxo-1H-indol-3-yl]acetonitrile
• SMILES (Canonical): COC1=CC=CC2=C1C(C(=O)N2)(CC#N)O
• SMILES (Isomeric): COC1=CC=CC2=C1[C@](C(=O)N2)(CC#N)O
• InChI: InChI=1S/C11H10N2O3/c1-16-8-4-2-3-7-9(8)11(15,5-6-12)10(14)13-7/h2-4,15H,5H2,1H3,(H,13,14)/t11-/m0/s1
• InChI Key: OYAAGDGYYVYWQP-NSHDSACASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀N₂O₃
• Molecular Weight: 218.21 g/mol
• Exact Mass: 218.06914219 g/mol
• Topological Polar Surface Area (TPSA): 82.40 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.75
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9607	96.07%
Caco-2	+	0.5253	52.53%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7014	70.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9617	96.17%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8150	81.50%
P-glycoprotein inhibitior	-	0.9729	97.29%
P-glycoprotein substrate	-	0.8409	84.09%
CYP3A4 substrate	+	0.5261	52.61%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.7111	71.11%
CYP3A4 inhibition	-	0.8563	85.63%
CYP2C9 inhibition	-	0.8341	83.41%
CYP2C19 inhibition	-	0.8304	83.04%
CYP2D6 inhibition	-	0.9157	91.57%
CYP1A2 inhibition	-	0.8145	81.45%
CYP2C8 inhibition	-	0.6501	65.01%
CYP inhibitory promiscuity	-	0.6852	68.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6173	61.73%
Eye corrosion	-	0.9903	99.03%
Eye irritation	+	0.5880	58.80%
Skin irritation	-	0.7998	79.98%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.6328	63.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.6377	63.77%
Micronuclear	+	0.8491	84.91%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.8676	86.76%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.7161	71.61%
Acute Oral Toxicity (c)	III	0.6182	61.82%
Estrogen receptor binding	+	0.6481	64.81%
Androgen receptor binding	+	0.5777	57.77%
Thyroid receptor binding	+	0.6347	63.47%
Glucocorticoid receptor binding	-	0.5630	56.30%
Aromatase binding	-	0.7342	73.42%
PPAR gamma	-	0.6612	66.12%
Honey bee toxicity	-	0.8763	87.63%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	-	0.8521	85.21%

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	97.79%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.04%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.39%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.74%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.31%	86.33%
CHEMBL2535	P11166	Glucose transporter	91.19%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.15%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.93%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.44%	94.00%
CHEMBL4208	P20618	Proteasome component C5	83.68%	90.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	83.45%	90.24%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.24%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	80.53%	90.17%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 60156060
• NPASS: NPC219383
• LOTUS: LTS0084241
• wikiData: Q105203081