2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one

Details

• Internal ID: e848d753-ea09-45dd-9f40-aaab4c8f619b
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: 2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one
• SMILES (Canonical): COC1=CC(=O)OC(C1)C=CC2=CC(=C(C=C2)OC)OC
• SMILES (Isomeric): COC1=CC(=O)OC(C1)/C=C/C2=CC(=C(C=C2)OC)OC
• InChI: InChI=1S/C16H18O5/c1-18-13-9-12(21-16(17)10-13)6-4-11-5-7-14(19-2)15(8-11)20-3/h4-8,10,12H,9H2,1-3H3/b6-4+
• InChI Key: FISBBPCLKKQWQA-GQCTYLIASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.31 g/mol
• Exact Mass: 290.11542367 g/mol
• Topological Polar Surface Area (TPSA): 54.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 5
• 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	+	0.9881	98.81%
Caco-2	+	0.9237	92.37%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6785	67.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9347	93.47%
OATP1B3 inhibitior	+	0.9681	96.81%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.6904	69.04%
P-glycoprotein inhibitior	-	0.4767	47.67%
P-glycoprotein substrate	-	0.8018	80.18%
CYP3A4 substrate	+	0.5309	53.09%
CYP2C9 substrate	-	0.8031	80.31%
CYP2D6 substrate	-	0.8498	84.98%
CYP3A4 inhibition	-	0.7799	77.99%
CYP2C9 inhibition	-	0.9816	98.16%
CYP2C19 inhibition	+	0.7328	73.28%
CYP2D6 inhibition	-	0.9089	90.89%
CYP1A2 inhibition	+	0.6560	65.60%
CYP2C8 inhibition	-	0.6362	63.62%
CYP inhibitory promiscuity	+	0.7442	74.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9046	90.46%
Carcinogenicity (trinary)	Non-required	0.5938	59.38%
Eye corrosion	-	0.9597	95.97%
Eye irritation	+	0.5284	52.84%
Skin irritation	-	0.7272	72.72%
Skin corrosion	-	0.9843	98.43%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6994	69.94%
Micronuclear	+	0.5518	55.18%
Hepatotoxicity	+	0.8875	88.75%
skin sensitisation	-	0.8597	85.97%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	-	0.5914	59.14%
Acute Oral Toxicity (c)	III	0.4049	40.49%
Estrogen receptor binding	+	0.7987	79.87%
Androgen receptor binding	+	0.7172	71.72%
Thyroid receptor binding	+	0.5659	56.59%
Glucocorticoid receptor binding	+	0.5689	56.89%
Aromatase binding	+	0.6626	66.26%
PPAR gamma	-	0.6338	63.38%
Honey bee toxicity	-	0.8129	81.29%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9513	95.13%

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	94.38%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.92%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.89%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.90%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	90.99%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.37%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.76%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.60%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.29%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.32%	97.09%
CHEMBL2535	P11166	Glucose transporter	83.10%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.90%	96.09%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.85%	92.38%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.49%	97.14%

Plants that contains it

• Piper methysticum

Cross-Links

• PubChem: 11572851
• NPASS: NPC303671