methyl 4-(1H-indol-3-yl)-2-methyl-4-oxobut-2-enoate

Details

• Internal ID: 2e6e9b9b-bb50-4fb0-8ab1-e0f877bcb16c
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles
• IUPAC Name: methyl 4-(1H-indol-3-yl)-2-methyl-4-oxobut-2-enoate
• SMILES (Canonical): CC(=CC(=O)C1=CNC2=CC=CC=C21)C(=O)OC
• SMILES (Isomeric): CC(=CC(=O)C1=CNC2=CC=CC=C21)C(=O)OC
• InChI: InChI=1S/C14H13NO3/c1-9(14(17)18-2)7-13(16)11-8-15-12-6-4-3-5-10(11)12/h3-8,15H,1-2H3
• InChI Key: DOTJZAALWJYBRD-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₃NO₃
• Molecular Weight: 243.26 g/mol
• Exact Mass: 243.08954328 g/mol
• Topological Polar Surface Area (TPSA): 59.20 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8928	89.28%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6863	68.63%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.9252	92.52%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6033	60.33%
P-glycoprotein inhibitior	-	0.8341	83.41%
P-glycoprotein substrate	-	0.8281	82.81%
CYP3A4 substrate	+	0.5455	54.55%
CYP2C9 substrate	+	0.8000	80.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.7215	72.15%
CYP2C9 inhibition	-	0.5940	59.40%
CYP2C19 inhibition	-	0.6211	62.11%
CYP2D6 inhibition	-	0.9091	90.91%
CYP1A2 inhibition	+	0.8532	85.32%
CYP2C8 inhibition	-	0.6873	68.73%
CYP inhibitory promiscuity	+	0.6650	66.50%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8353	83.53%
Carcinogenicity (trinary)	Non-required	0.5845	58.45%
Eye corrosion	-	0.9818	98.18%
Eye irritation	-	0.6396	63.96%
Skin irritation	-	0.8051	80.51%
Skin corrosion	-	0.9772	97.72%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7327	73.27%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8259	82.59%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5210	52.10%
Acute Oral Toxicity (c)	III	0.6253	62.53%
Estrogen receptor binding	+	0.8869	88.69%
Androgen receptor binding	-	0.5469	54.69%
Thyroid receptor binding	+	0.5837	58.37%
Glucocorticoid receptor binding	+	0.7948	79.48%
Aromatase binding	+	0.8247	82.47%
PPAR gamma	-	0.5456	54.56%
Honey bee toxicity	-	0.8689	86.89%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8795	87.95%

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	98.08%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.72%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.40%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.51%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.24%	98.95%
CHEMBL2535	P11166	Glucose transporter	89.22%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	84.11%	94.73%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	83.42%	96.47%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.17%	95.50%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	82.07%	83.10%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.42%	94.62%

Plants that contains it

• Murraya paniculata

Cross-Links

• PubChem: 73159299
• LOTUS: LTS0255752
• wikiData: Q104986181