(E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone

Details

• Internal ID: da617a4a-f2c3-4886-bbaf-bf21e93c4bbd
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: (E)-1-(2,4-dihydroxy-6-methoxy-3,5-dimethylphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• InChI: InChI=1S/C18H18O5/c1-10-16(21)11(2)18(23-3)15(17(10)22)14(20)9-6-12-4-7-13(19)8-5-12/h4-9,19,21-22H,1-3H3/b9-6+
• InChI Key: HTDSMOBGCNRBHQ-RMKNXTFCSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₅
• Molecular Weight: 314.30 g/mol
• Exact Mass: 314.11542367 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.32
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• CHEMBL1271157
• (E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone
• SCHEMBL662283
• BDBM50482872
• Q27138987
• (2E)-1-(2,4-dihydroxy-6-methoxy-3,5-dimethylphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• (e)-1-(2,4-dihydroxy-6-methoxy-3,5-dimethylphenyl)-3-(4-hydroxy-phenyl)prop-2-en-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9854	98.54%
Caco-2	+	0.7067	70.67%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7916	79.16%
OATP2B1 inhibitior	+	0.5600	56.00%
OATP1B1 inhibitior	+	0.8536	85.36%
OATP1B3 inhibitior	+	0.9184	91.84%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5981	59.81%
P-glycoprotein inhibitior	-	0.7351	73.51%
P-glycoprotein substrate	-	0.8984	89.84%
CYP3A4 substrate	-	0.5139	51.39%
CYP2C9 substrate	-	0.7931	79.31%
CYP2D6 substrate	-	0.8493	84.93%
CYP3A4 inhibition	+	0.7808	78.08%
CYP2C9 inhibition	+	0.5171	51.71%
CYP2C19 inhibition	+	0.7990	79.90%
CYP2D6 inhibition	-	0.8763	87.63%
CYP1A2 inhibition	+	0.8942	89.42%
CYP2C8 inhibition	+	0.6488	64.88%
CYP inhibitory promiscuity	+	0.8579	85.79%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7527	75.27%
Carcinogenicity (trinary)	Non-required	0.6629	66.29%
Eye corrosion	-	0.9757	97.57%
Eye irritation	+	0.8053	80.53%
Skin irritation	-	0.7638	76.38%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7210	72.10%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	-	0.7312	73.12%
skin sensitisation	-	0.8231	82.31%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.8045	80.45%
Acute Oral Toxicity (c)	III	0.6631	66.31%
Estrogen receptor binding	+	0.8295	82.95%
Androgen receptor binding	+	0.7195	71.95%
Thyroid receptor binding	+	0.7218	72.18%
Glucocorticoid receptor binding	+	0.8390	83.90%
Aromatase binding	+	0.7183	71.83%
PPAR gamma	+	0.8240	82.40%
Honey bee toxicity	-	0.9389	93.89%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6355	63.55%
Fish aquatic toxicity	+	0.9874	98.74%

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	93.18%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.30%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.94%	96.00%
CHEMBL3194	P02766	Transthyretin	88.71%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.92%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.57%	91.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.54%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.58%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.43%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.67%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.30%	95.50%

Plants that contains it

• Syzygium nervosum

Cross-Links

• PubChem: 49831446
• LOTUS: LTS0020997
• wikiData: Q27138987