5-Hydroxy-4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one

Details

• Internal ID: 89c18f4c-e4ce-4d69-96d2-9b54b2a0bb61
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: 3-hydroxy-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
• SMILES (Canonical): COC1=CC(=O)OC(C1O)CCC2=CC=CC=C2
• SMILES (Isomeric): COC1=CC(=O)OC(C1O)CCC2=CC=CC=C2
• InChI: InChI=1S/C14H16O4/c1-17-12-9-13(15)18-11(14(12)16)8-7-10-5-3-2-4-6-10/h2-6,9,11,14,16H,7-8H2,1H3
• InChI Key: VJCNEDVMYQCMBK-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.27 g/mol
• Exact Mass: 248.10485899 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 5-Hydroxy-4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one
• 3-hydroxy-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
• (+)-cis-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one
• 52247-81-1
• SCHEMBL9016220
• CHEBI:174280
• VJCNEDVMYQCMBK-UHFFFAOYSA-N
• 5-Hydroxy-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one
• 2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8640	86.40%
Caco-2	+	0.7828	78.28%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8135	81.35%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.8835	88.35%
OATP1B3 inhibitior	+	0.9534	95.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.7871	78.71%
P-glycoprotein inhibitior	-	0.7559	75.59%
P-glycoprotein substrate	-	0.8492	84.92%
CYP3A4 substrate	-	0.5088	50.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8567	85.67%
CYP3A4 inhibition	-	0.8857	88.57%
CYP2C9 inhibition	-	0.8605	86.05%
CYP2C19 inhibition	-	0.5080	50.80%
CYP2D6 inhibition	-	0.9046	90.46%
CYP1A2 inhibition	-	0.7695	76.95%
CYP2C8 inhibition	-	0.6822	68.22%
CYP inhibitory promiscuity	-	0.5697	56.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.5403	54.03%
Eye corrosion	-	0.9690	96.90%
Eye irritation	-	0.7056	70.56%
Skin irritation	-	0.6839	68.39%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5288	52.88%
Micronuclear	-	0.6782	67.82%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8656	86.56%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7489	74.89%
Acute Oral Toxicity (c)	III	0.5305	53.05%
Estrogen receptor binding	+	0.6068	60.68%
Androgen receptor binding	+	0.6168	61.68%
Thyroid receptor binding	-	0.7371	73.71%
Glucocorticoid receptor binding	-	0.6630	66.30%
Aromatase binding	-	0.7559	75.59%
PPAR gamma	-	0.8319	83.19%
Honey bee toxicity	-	0.8938	89.38%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	-	0.3632	36.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.24%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.03%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.65%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.79%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.65%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.49%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	84.41%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.86%	95.50%

Plants that contains it

• Piper methysticum

Cross-Links

• PubChem: 575067
• LOTUS: LTS0043963
• wikiData: Q105287159