1H-Indole-3-acetic acid, 2,3-dihydro-3-hydroxy-2-oxo-

Details

• Internal ID: 6bf63a15-a78b-4ca3-93d5-b90679ef1cea
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolyl carboxylic acids and derivatives
• IUPAC Name: 2-(3-hydroxy-2-oxo-1H-indol-3-yl)acetic acid
• SMILES (Canonical): C1=CC=C2C(=C1)C(C(=O)N2)(CC(=O)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C(C(=O)N2)(CC(=O)O)O
• InChI: InChI=1S/C10H9NO4/c12-8(13)5-10(15)6-3-1-2-4-7(6)11-9(10)14/h1-4,15H,5H2,(H,11,14)(H,12,13)
• InChI Key: MHLHEINWUCSPTL-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₉NO₄
• Molecular Weight: 207.18 g/mol
• Exact Mass: 207.05315777 g/mol
• Topological Polar Surface Area (TPSA): 86.60 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 57061-17-3
• 2-(3-Hydroxy-2-oxoindolin-3-yl)-acetic acid
• 2-(3-hydroxy-2-oxo-1H-indol-3-yl)acetic Acid
• SCHEMBL1460831
• DTXSID50440735
• CHEBI:181565
• 3-hydroxy-2-oxindole-3-acetic acid
• HY-N10668
• NCGC00385842-01
• CS-0634291
• NCGC00385842-01_C10H9NO4_(3-Hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6704	67.04%
Caco-2	+	0.4903	49.03%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5822	58.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9303	93.03%
OATP1B3 inhibitior	+	0.9433	94.33%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9409	94.09%
P-glycoprotein inhibitior	-	0.9908	99.08%
P-glycoprotein substrate	-	0.9406	94.06%
CYP3A4 substrate	-	0.6154	61.54%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.7970	79.70%
CYP3A4 inhibition	-	0.9724	97.24%
CYP2C9 inhibition	-	0.9577	95.77%
CYP2C19 inhibition	-	0.9527	95.27%
CYP2D6 inhibition	-	0.9561	95.61%
CYP1A2 inhibition	-	0.9126	91.26%
CYP2C8 inhibition	-	0.9176	91.76%
CYP inhibitory promiscuity	-	0.9585	95.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6290	62.90%
Eye corrosion	-	0.9926	99.26%
Eye irritation	+	0.7443	74.43%
Skin irritation	-	0.7852	78.52%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9387	93.87%
Micronuclear	+	0.8459	84.59%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8573	85.73%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.4599	45.99%
Acute Oral Toxicity (c)	III	0.5603	56.03%
Estrogen receptor binding	-	0.8318	83.18%
Androgen receptor binding	-	0.5075	50.75%
Thyroid receptor binding	-	0.6196	61.96%
Glucocorticoid receptor binding	-	0.5179	51.79%
Aromatase binding	-	0.6211	62.11%
PPAR gamma	+	0.7668	76.68%
Honey bee toxicity	-	0.9892	98.92%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	-	0.6160	61.60%

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	94.48%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.93%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.79%	98.95%
CHEMBL4208	P20618	Proteasome component C5	93.66%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.39%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	89.18%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.60%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.47%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.12%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.81%	99.23%

Plants that contains it

• Prunus cerasus

Cross-Links

• PubChem: 10488522
• LOTUS: LTS0116658
• wikiData: Q82257119