2-Oxo-2H-indole-3-acetic acid

Details

• Internal ID: 8326828b-e9ec-43ce-90e5-a6a6ad257dd9
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolyl carboxylic acids and derivatives
• IUPAC Name: 2-(2-oxoindol-3-yl)acetic acid
• SMILES (Canonical): C1=CC2=C(C(=O)N=C2C=C1)CC(=O)O
• SMILES (Isomeric): C1=CC2=C(C(=O)N=C2C=C1)CC(=O)O
• InChI: InChI=1S/C10H7NO3/c12-9(13)5-7-6-3-1-2-4-8(6)11-10(7)14/h1-4H,5H2,(H,12,13)
• InChI Key: OINWOHIZFCLCPY-UHFFFAOYSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₇NO₃
• Molecular Weight: 189.17 g/mol
• Exact Mass: 189.042593085 g/mol
• Topological Polar Surface Area (TPSA): 66.70 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -0.53
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	-	0.6240	62.40%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5144	51.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9336	93.36%
OATP1B3 inhibitior	+	0.9436	94.36%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8928	89.28%
P-glycoprotein inhibitior	-	0.9930	99.30%
P-glycoprotein substrate	-	0.9748	97.48%
CYP3A4 substrate	-	0.6932	69.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8630	86.30%
CYP3A4 inhibition	-	0.8109	81.09%
CYP2C9 inhibition	-	0.7399	73.99%
CYP2C19 inhibition	-	0.8277	82.77%
CYP2D6 inhibition	-	0.8100	81.00%
CYP1A2 inhibition	+	0.5317	53.17%
CYP2C8 inhibition	-	0.8381	83.81%
CYP inhibitory promiscuity	-	0.8741	87.41%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7100	71.00%
Carcinogenicity (trinary)	Non-required	0.5944	59.44%
Eye corrosion	-	0.9638	96.38%
Eye irritation	+	0.8051	80.51%
Skin irritation	-	0.6978	69.78%
Skin corrosion	-	0.9325	93.25%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8188	81.88%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.7254	72.54%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6933	69.33%
Acute Oral Toxicity (c)	III	0.5272	52.72%
Estrogen receptor binding	-	0.8271	82.71%
Androgen receptor binding	-	0.6660	66.60%
Thyroid receptor binding	-	0.7621	76.21%
Glucocorticoid receptor binding	+	0.6451	64.51%
Aromatase binding	-	0.4834	48.34%
PPAR gamma	+	0.8374	83.74%
Honey bee toxicity	-	0.9759	97.59%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8765	87.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.38%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	91.26%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.56%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.86%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.63%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	88.23%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.48%	91.11%

Plants that contains it

• Arabidopsis thaliana
• Pinus sylvestris
• Solanum lycopersicum
• Zea mays

Cross-Links

• PubChem: 11788737
• LOTUS: LTS0048565
• wikiData: Q105192629