(2S,3S)-3-hydroxy-2,4-dimethoxy-2-[(E)-2-phenylethenyl]-3H-pyran-6-one

Details

• Internal ID: 9a5f5457-7e00-4f6b-9185-32c1a4113ee0
• Taxonomy: Phenylpropanoids and polyketides > Kavalactones
• IUPAC Name: (2S,3S)-3-hydroxy-2,4-dimethoxy-2-[(E)-2-phenylethenyl]-3H-pyran-6-one
• SMILES (Canonical): COC1=CC(=O)OC(C1O)(C=CC2=CC=CC=C2)OC
• SMILES (Isomeric): COC1=CC(=O)O[C@]([C@H]1O)(/C=C/C2=CC=CC=C2)OC
• InChI: InChI=1S/C15H16O5/c1-18-12-10-13(16)20-15(19-2,14(12)17)9-8-11-6-4-3-5-7-11/h3-10,14,17H,1-2H3/b9-8+/t14-,15-/m0/s1
• InChI Key: MHYAXKUAGKFFHV-JJGIJDNGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.09977361 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9014	90.14%
Caco-2	+	0.8159	81.59%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7864	78.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9022	90.22%
OATP1B3 inhibitior	+	0.9644	96.44%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5270	52.70%
P-glycoprotein inhibitior	-	0.7373	73.73%
P-glycoprotein substrate	-	0.9290	92.90%
CYP3A4 substrate	+	0.5151	51.51%
CYP2C9 substrate	-	0.8245	82.45%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	-	0.7707	77.07%
CYP2C9 inhibition	-	0.9721	97.21%
CYP2C19 inhibition	-	0.5545	55.45%
CYP2D6 inhibition	-	0.9404	94.04%
CYP1A2 inhibition	-	0.8785	87.85%
CYP2C8 inhibition	-	0.5949	59.49%
CYP inhibitory promiscuity	-	0.5784	57.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8356	83.56%
Carcinogenicity (trinary)	Danger	0.4459	44.59%
Eye corrosion	-	0.9488	94.88%
Eye irritation	-	0.6070	60.70%
Skin irritation	-	0.6104	61.04%
Skin corrosion	-	0.9815	98.15%
Ames mutagenesis	+	0.5592	55.92%
Human Ether-a-go-go-Related Gene inhibition	-	0.6826	68.26%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.5929	59.29%
skin sensitisation	-	0.8135	81.35%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	+	0.6278	62.78%
Acute Oral Toxicity (c)	III	0.4583	45.83%
Estrogen receptor binding	+	0.8313	83.13%
Androgen receptor binding	+	0.6698	66.98%
Thyroid receptor binding	-	0.5929	59.29%
Glucocorticoid receptor binding	+	0.5459	54.59%
Aromatase binding	+	0.5687	56.87%
PPAR gamma	+	0.5173	51.73%
Honey bee toxicity	-	0.8564	85.64%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.8638	86.38%

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	96.81%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.32%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.00%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.97%	96.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.42%	94.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.44%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.39%	94.62%
CHEMBL221	P23219	Cyclooxygenase-1	85.62%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.63%	99.23%
CHEMBL2581	P07339	Cathepsin D	83.57%	98.95%

Plants that contains it

• Piper auritum

Cross-Links

• PubChem: 163188510
• LOTUS: LTS0068509
• wikiData: Q105164400