3-(4-Methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one

Details

• Internal ID: dc2b5bd7-43b6-47f7-9fe8-8a587033f165
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: 3-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): COC1=CC=C(C=C1)C=CC(=O)C2=C(C=C(C=C2O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C=CC(=O)C2=C(C=C(C=C2O)O)O
• InChI: InChI=1S/C16H14O5/c1-21-12-5-2-10(3-6-12)4-7-13(18)16-14(19)8-11(17)9-15(16)20/h2-9,17,19-20H,1H3
• InChI Key: DGUBZDXYXXUHTJ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.71
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9869	98.69%
Caco-2	+	0.9263	92.63%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8037	80.37%
OATP2B1 inhibitior	-	0.7017	70.17%
OATP1B1 inhibitior	+	0.9491	94.91%
OATP1B3 inhibitior	+	0.9790	97.90%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9838	98.38%
BSEP inhibitior	-	0.5335	53.35%
P-glycoprotein inhibitior	-	0.8525	85.25%
P-glycoprotein substrate	-	0.9562	95.62%
CYP3A4 substrate	-	0.5655	56.55%
CYP2C9 substrate	-	0.8053	80.53%
CYP2D6 substrate	-	0.8356	83.56%
CYP3A4 inhibition	+	0.6964	69.64%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	+	0.9352	93.52%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9657	96.57%
CYP2C8 inhibition	+	0.6274	62.74%
CYP inhibitory promiscuity	+	0.8838	88.38%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7527	75.27%
Carcinogenicity (trinary)	Non-required	0.6543	65.43%
Eye corrosion	-	0.9650	96.50%
Eye irritation	+	0.9493	94.93%
Skin irritation	-	0.5765	57.65%
Skin corrosion	-	0.8424	84.24%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6170	61.70%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.6092	60.92%
skin sensitisation	-	0.7282	72.82%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.6065	60.65%
Acute Oral Toxicity (c)	III	0.6317	63.17%
Estrogen receptor binding	+	0.9239	92.39%
Androgen receptor binding	+	0.8761	87.61%
Thyroid receptor binding	+	0.7553	75.53%
Glucocorticoid receptor binding	+	0.8427	84.27%
Aromatase binding	+	0.9203	92.03%
PPAR gamma	+	0.8909	89.09%
Honey bee toxicity	-	0.9403	94.03%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9829	98.29%

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	97.87%	91.11%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.67%	96.12%
CHEMBL4208	P20618	Proteasome component C5	95.31%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.95%	95.56%
CHEMBL3194	P02766	Transthyretin	93.07%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.81%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.50%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.21%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.61%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.77%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.70%	95.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.65%	93.99%
CHEMBL2535	P11166	Glucose transporter	80.14%	98.75%

Plants that contains it

• Wyethia glabra

Cross-Links

• PubChem: 53759355
• LOTUS: LTS0242666
• wikiData: Q104979288