Chalcone, 4-hydroxy-2',4'-dimethoxy-

Details

• Internal ID: aa8722af-cfe8-4a59-b33d-2386b5c5ff24
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Cinnamylphenols
• IUPAC Name: (E)-1-(2,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): COC1=CC(=C(C=C1)C(=O)C=CC2=CC=C(C=C2)O)OC
• SMILES (Isomeric): COC1=CC(=C(C=C1)C(=O)/C=C/C2=CC=C(C=C2)O)OC
• InChI: InChI=1S/C17H16O4/c1-20-14-8-9-15(17(11-14)21-2)16(19)10-5-12-3-6-13(18)7-4-12/h3-11,18H,1-2H3/b10-5+
• InChI Key: ATHWOBRNXTYZEM-BJMVGYQFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31 g/mol
• Exact Mass: 284.10485899 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.31
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 23423-35-0
• CHEMBL1774612
• SCHEMBL21527708
• (E)-1-(2,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• 2',4'-dimethoxy 4-hydroxy chalcone
• AKOS002719829

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	+	0.9137	91.37%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8978	89.78%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.9342	93.42%
OATP1B3 inhibitior	+	0.9897	98.97%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.5575	55.75%
P-glycoprotein inhibitior	-	0.5902	59.02%
P-glycoprotein substrate	-	0.9117	91.17%
CYP3A4 substrate	-	0.5369	53.69%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.7972	79.72%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.9037	90.37%
CYP2C19 inhibition	+	0.8684	86.84%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.8968	89.68%
CYP2C8 inhibition	+	0.7863	78.63%
CYP inhibitory promiscuity	+	0.7605	76.05%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6960	69.60%
Carcinogenicity (trinary)	Non-required	0.6565	65.65%
Eye corrosion	-	0.9569	95.69%
Eye irritation	+	0.8567	85.67%
Skin irritation	-	0.6490	64.90%
Skin corrosion	-	0.9851	98.51%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6338	63.38%
Micronuclear	+	0.6233	62.33%
Hepatotoxicity	-	0.7151	71.51%
skin sensitisation	-	0.8735	87.35%
Respiratory toxicity	-	0.9444	94.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	+	0.5130	51.30%
Acute Oral Toxicity (c)	III	0.6034	60.34%
Estrogen receptor binding	+	0.9459	94.59%
Androgen receptor binding	+	0.9114	91.14%
Thyroid receptor binding	+	0.7000	70.00%
Glucocorticoid receptor binding	+	0.7693	76.93%
Aromatase binding	+	0.8458	84.58%
PPAR gamma	+	0.8497	84.97%
Honey bee toxicity	-	0.9187	91.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9891	98.91%

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	96.23%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.16%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.98%	86.33%
CHEMBL4208	P20618	Proteasome component C5	92.79%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.61%	96.09%
CHEMBL2535	P11166	Glucose transporter	90.48%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.48%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.07%	96.00%
CHEMBL3194	P02766	Transthyretin	89.96%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.14%	95.50%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.49%	91.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.62%	91.07%

Plants that contains it

• Koompassia malaccensis

Cross-Links

• PubChem: 6171845
• LOTUS: LTS0150974
• wikiData: Q76323670