1H-Indole-3-acetic acid, 2,3-dihydro-2-oxo-, methyl ester

Details

• Internal ID: e385c9b5-9c8d-4b86-b7f1-653f2d297073
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolyl carboxylic acids and derivatives
• IUPAC Name: methyl 2-(2-oxo-1,3-dihydroindol-3-yl)acetate
• SMILES (Canonical): COC(=O)CC1C2=CC=CC=C2NC1=O
• SMILES (Isomeric): COC(=O)CC1C2=CC=CC=C2NC1=O
• InChI: InChI=1S/C11H11NO3/c1-15-10(13)6-8-7-4-2-3-5-9(7)12-11(8)14/h2-5,8H,6H2,1H3,(H,12,14)
• InChI Key: OEGSDTIXVSKASM-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21 g/mol
• Exact Mass: 205.07389321 g/mol
• Topological Polar Surface Area (TPSA): 55.40 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 1H-Indole-3-acetic acid, 2,3-dihydro-2-oxo-, methyl ester
• Methyl 2-(2-oxo-1,3-dihydroindol-3-yl)acetate
• DTXSID10461229
• RefChem:239033
• DTXCID00412048
• methyl oxindole-3-acetate
• Methyl 2-(2-oxoindolin-3-yl)acetate
• methyl 2-(2-oxo-2,3-dihydro-1H-indol-3-yl)acetate
• starbld0035723
• SCHEMBL1750987
• SCHEMBL8998987
• CHEMBL3904125
• MFCD18459240
• AKOS005264222
• Methyl (2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.5648	56.48%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6523	65.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8629	86.29%
OATP1B3 inhibitior	+	0.9536	95.36%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8482	84.82%
P-glycoprotein inhibitior	-	0.9835	98.35%
P-glycoprotein substrate	-	0.7435	74.35%
CYP3A4 substrate	+	0.5676	56.76%
CYP2C9 substrate	-	0.5855	58.55%
CYP2D6 substrate	-	0.7598	75.98%
CYP3A4 inhibition	-	0.7925	79.25%
CYP2C9 inhibition	-	0.8019	80.19%
CYP2C19 inhibition	-	0.8261	82.61%
CYP2D6 inhibition	-	0.9497	94.97%
CYP1A2 inhibition	+	0.7760	77.60%
CYP2C8 inhibition	-	0.5971	59.71%
CYP inhibitory promiscuity	-	0.7919	79.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6423	64.23%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.5525	55.25%
Skin irritation	-	0.8354	83.54%
Skin corrosion	-	0.9628	96.28%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5543	55.43%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.5296	52.96%
skin sensitisation	-	0.9141	91.41%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.5624	56.24%
Acute Oral Toxicity (c)	III	0.6682	66.82%
Estrogen receptor binding	-	0.7599	75.99%
Androgen receptor binding	+	0.6478	64.78%
Thyroid receptor binding	-	0.7052	70.52%
Glucocorticoid receptor binding	-	0.5296	52.96%
Aromatase binding	-	0.6183	61.83%
PPAR gamma	+	0.5247	52.47%
Honey bee toxicity	-	0.9286	92.86%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8202	82.02%

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	97.47%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.74%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.14%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.09%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.22%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.10%	94.45%
CHEMBL4208	P20618	Proteasome component C5	83.81%	90.00%
CHEMBL5028	O14672	ADAM10	81.65%	97.50%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.74%	89.67%

Plants that contains it

• Oenothera speciosa

Cross-Links

• PubChem: 11287197
• LOTUS: LTS0003578
• wikiData: Q82285502