(3E)-4-[3-(2-hydroxyethyl)-1H-indol-5-yl]but-3-en-2-one

Details

• Internal ID: 95b371a2-fad7-4732-9f4e-20be7cdf5f42
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives
• IUPAC Name: (E)-4-[3-(2-hydroxyethyl)-1H-indol-5-yl]but-3-en-2-one
• SMILES (Canonical): CC(=O)C=CC1=CC2=C(C=C1)NC=C2CCO
• SMILES (Isomeric): CC(=O)/C=C/C1=CC2=C(C=C1)NC=C2CCO
• InChI: InChI=1S/C14H15NO2/c1-10(17)2-3-11-4-5-14-13(8-11)12(6-7-16)9-15-14/h2-5,8-9,15-16H,6-7H2,1H3/b3-2+
• InChI Key: WVZBZDMTKRSQSU-NSCUHMNNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₅NO₂
• Molecular Weight: 229.27 g/mol
• Exact Mass: 229.110278721 g/mol
• Topological Polar Surface Area (TPSA): 53.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.30
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• (3E)-4-[3-(2-hydroxyethyl)-1H-indol-5-yl]but-3-en-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.6617	66.17%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5799	57.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9219	92.19%
OATP1B3 inhibitior	+	0.9548	95.48%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6983	69.83%
P-glycoprotein inhibitior	-	0.9803	98.03%
P-glycoprotein substrate	-	0.7498	74.98%
CYP3A4 substrate	-	0.5360	53.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8169	81.69%
CYP3A4 inhibition	-	0.7720	77.20%
CYP2C9 inhibition	-	0.6231	62.31%
CYP2C19 inhibition	-	0.5908	59.08%
CYP2D6 inhibition	-	0.8640	86.40%
CYP1A2 inhibition	+	0.6090	60.90%
CYP2C8 inhibition	-	0.7086	70.86%
CYP inhibitory promiscuity	-	0.5892	58.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6392	63.92%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8084	80.84%
Skin irritation	-	0.7692	76.92%
Skin corrosion	-	0.9196	91.96%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7880	78.80%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.6917	69.17%
skin sensitisation	-	0.8164	81.64%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7652	76.52%
Acute Oral Toxicity (c)	III	0.7259	72.59%
Estrogen receptor binding	-	0.5437	54.37%
Androgen receptor binding	-	0.6979	69.79%
Thyroid receptor binding	-	0.5849	58.49%
Glucocorticoid receptor binding	+	0.5415	54.15%
Aromatase binding	+	0.5736	57.36%
PPAR gamma	+	0.6505	65.05%
Honey bee toxicity	-	0.9401	94.01%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.8748	87.48%

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	98.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.41%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.69%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.61%	96.00%
CHEMBL2581	P07339	Cathepsin D	90.08%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.90%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.23%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.56%	89.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.84%	91.71%
CHEMBL255	P29275	Adenosine A2b receptor	84.99%	98.59%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	83.36%	90.71%
CHEMBL1937	Q92769	Histone deacetylase 2	81.47%	94.75%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 90675403
• LOTUS: LTS0026979
• wikiData: Q77492568