(2R)-4-methoxy-5-methyl-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one

Details

• Internal ID: d0ce38c5-92da-43d3-86ee-65477c4bcc78
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: (2R)-4-methoxy-5-methyl-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(CC(OC1=O)C=CC2=CC=CC=C2)OC
• SMILES (Isomeric): CC1=C(C[C@@H](OC1=O)/C=C/C2=CC=CC=C2)OC
• InChI: InChI=1S/C15H16O3/c1-11-14(17-2)10-13(18-15(11)16)9-8-12-6-4-3-5-7-12/h3-9,13H,10H2,1-2H3/b9-8+/t13-/m0/s1
• InChI Key: CSMBYJHAWMUEKM-XEHSLEBBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.28 g/mol
• Exact Mass: 244.109944368 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.94
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.8789	87.89%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7831	78.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9210	92.10%
OATP1B3 inhibitior	+	0.9691	96.91%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.4776	47.76%
P-glycoprotein inhibitior	-	0.7994	79.94%
P-glycoprotein substrate	-	0.9470	94.70%
CYP3A4 substrate	-	0.5504	55.04%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8655	86.55%
CYP3A4 inhibition	-	0.8077	80.77%
CYP2C9 inhibition	-	0.9342	93.42%
CYP2C19 inhibition	+	0.8046	80.46%
CYP2D6 inhibition	-	0.9234	92.34%
CYP1A2 inhibition	+	0.7162	71.62%
CYP2C8 inhibition	-	0.7774	77.74%
CYP inhibitory promiscuity	+	0.7339	73.39%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8058	80.58%
Carcinogenicity (trinary)	Non-required	0.6379	63.79%
Eye corrosion	-	0.9369	93.69%
Eye irritation	-	0.7496	74.96%
Skin irritation	-	0.5817	58.17%
Skin corrosion	-	0.9869	98.69%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7145	71.45%
Micronuclear	-	0.5256	52.56%
Hepatotoxicity	+	0.7193	71.93%
skin sensitisation	-	0.7319	73.19%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	+	0.4725	47.25%
Acute Oral Toxicity (c)	III	0.5448	54.48%
Estrogen receptor binding	-	0.6713	67.13%
Androgen receptor binding	+	0.5859	58.59%
Thyroid receptor binding	-	0.7344	73.44%
Glucocorticoid receptor binding	-	0.8303	83.03%
Aromatase binding	-	0.4885	48.85%
PPAR gamma	-	0.7452	74.52%
Honey bee toxicity	-	0.7996	79.96%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.9098	90.98%

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	96.74%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.62%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.97%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.10%	93.99%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.89%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.35%	85.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.12%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.01%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.75%	94.62%
CHEMBL2581	P07339	Cathepsin D	81.94%	98.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163190912
• LOTUS: LTS0255732
• wikiData: Q104969432