[2,4-dimethoxy-6-oxo-2-(2-phenylethenyl)-3H-pyran-3-yl] acetate

Details

• Internal ID: 1bbbf6d2-0891-4b6d-9552-cfbe68c69c10
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: [2,4-dimethoxy-6-oxo-2-(2-phenylethenyl)-3H-pyran-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(=CC(=O)OC1(C=CC2=CC=CC=C2)OC)OC
• SMILES (Isomeric): CC(=O)OC1C(=CC(=O)OC1(C=CC2=CC=CC=C2)OC)OC
• InChI: InChI=1S/C17H18O6/c1-12(18)22-16-14(20-2)11-15(19)23-17(16,21-3)10-9-13-7-5-4-6-8-13/h4-11,16H,1-3H3
• InChI Key: REYHFHICSRTQSJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.32 g/mol
• Exact Mass: 318.11033829 g/mol
• Topological Polar Surface Area (TPSA): 71.10 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.06
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9276	92.76%
Caco-2	+	0.7411	74.11%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7589	75.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8964	89.64%
OATP1B3 inhibitior	+	0.9637	96.37%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5055	50.55%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8804	88.04%
CYP3A4 substrate	+	0.5658	56.58%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.8879	88.79%
CYP3A4 inhibition	-	0.6634	66.34%
CYP2C9 inhibition	-	0.9797	97.97%
CYP2C19 inhibition	-	0.6682	66.82%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.6516	65.16%
CYP2C8 inhibition	+	0.4569	45.69%
CYP inhibitory promiscuity	+	0.5077	50.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8446	84.46%
Carcinogenicity (trinary)	Danger	0.4540	45.40%
Eye corrosion	-	0.9479	94.79%
Eye irritation	-	0.6333	63.33%
Skin irritation	-	0.7521	75.21%
Skin corrosion	-	0.9829	98.29%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6540	65.40%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.6584	65.84%
skin sensitisation	-	0.8436	84.36%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	+	0.6002	60.02%
Acute Oral Toxicity (c)	III	0.3956	39.56%
Estrogen receptor binding	+	0.8752	87.52%
Androgen receptor binding	+	0.7421	74.21%
Thyroid receptor binding	-	0.5171	51.71%
Glucocorticoid receptor binding	-	0.5501	55.01%
Aromatase binding	+	0.6192	61.92%
PPAR gamma	+	0.5307	53.07%
Honey bee toxicity	-	0.7630	76.30%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9370	93.70%

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	97.93%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.29%	86.33%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	93.66%	94.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.49%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.72%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.82%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.64%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.81%	85.14%
CHEMBL5028	O14672	ADAM10	86.34%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.52%	99.23%
CHEMBL2581	P07339	Cathepsin D	83.49%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.55%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.54%	89.00%

Plants that contains it

• Piper sanctum

Cross-Links

• PubChem: 71438811
• LOTUS: LTS0269622
• wikiData: Q105235185