4-Methoxy-6-(2-phenylethenyl)-2h-pyran-2-one

Details

• Internal ID: ae62f0ba-1f42-462b-991b-5cc19b2507bd
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: 4-methoxy-6-(2-phenylethenyl)pyran-2-one
• SMILES (Canonical): COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2
• SMILES (Isomeric): COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2
• InChI: InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3
• InChI Key: DKKJNZYHGRUXBS-UHFFFAOYSA-N
• Popularity: 25 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24 g/mol
• Exact Mass: 228.078644241 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.82
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 4-methoxy-6-styryl-pyran-2-one
• DTXSID70860158
• FT-0637217

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.9236	92.36%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7699	76.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9310	93.10%
OATP1B3 inhibitior	+	0.9885	98.85%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.5604	56.04%
P-glycoprotein inhibitior	-	0.5563	55.63%
P-glycoprotein substrate	-	0.9730	97.30%
CYP3A4 substrate	-	0.6222	62.22%
CYP2C9 substrate	-	0.8019	80.19%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.7925	79.25%
CYP2C9 inhibition	-	0.6256	62.56%
CYP2C19 inhibition	+	0.9179	91.79%
CYP2D6 inhibition	-	0.9132	91.32%
CYP1A2 inhibition	+	0.9460	94.60%
CYP2C8 inhibition	-	0.6267	62.67%
CYP inhibitory promiscuity	+	0.7846	78.46%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8341	83.41%
Carcinogenicity (trinary)	Non-required	0.4000	40.00%
Eye corrosion	-	0.6804	68.04%
Eye irritation	+	0.8419	84.19%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9753	97.53%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5307	53.07%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5658	56.58%
skin sensitisation	-	0.8517	85.17%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.5251	52.51%
Acute Oral Toxicity (c)	III	0.6806	68.06%
Estrogen receptor binding	+	0.9403	94.03%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	-	0.5614	56.14%
Glucocorticoid receptor binding	-	0.4888	48.88%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.6813	68.13%
Honey bee toxicity	-	0.9254	92.54%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.9209	92.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.81%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.15%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.10%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.96%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.95%	95.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.25%	93.99%
CHEMBL2581	P07339	Cathepsin D	87.55%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	84.95%	94.73%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.31%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.90%	94.62%
CHEMBL1907	P15144	Aminopeptidase N	80.84%	93.31%

Plants that contains it

• Alpinia mutica
• Alpinia roxburghii
• Alpinia zerumbet
• Aniba firmula
• Aniba permollis
• Boesenbergia rotunda
• Lindera umbellata
• Piper methysticum
• Piper sanctum
• Piper sarmentosum

Cross-Links

• PubChem: 164901
• LOTUS: LTS0009498
• wikiData: Q104983396