1-(3,4-Dihydroxyphenyl)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one

Details

• Internal ID: b589876c-f5d8-4bce-bed2-ff3b90d657c4
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retrochalcones
• IUPAC Name: 1-(3,4-dihydroxyphenyl)-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-en-1-one
• InChI: InChI=1S/C21H22O5/c1-13(2)4-8-16-18(23)10-6-14(21(16)26-3)5-9-17(22)15-7-11-19(24)20(25)12-15/h4-7,9-12,23-25H,8H2,1-3H3
• InChI Key: RDYZHQQZLIBKBP-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.14672380 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.22
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9920	99.20%
Caco-2	+	0.6871	68.71%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7717	77.17%
OATP2B1 inhibitior	+	0.5671	56.71%
OATP1B1 inhibitior	+	0.8903	89.03%
OATP1B3 inhibitior	+	0.9017	90.17%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7551	75.51%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8215	82.15%
CYP3A4 substrate	+	0.5128	51.28%
CYP2C9 substrate	-	0.5904	59.04%
CYP2D6 substrate	-	0.7908	79.08%
CYP3A4 inhibition	-	0.8095	80.95%
CYP2C9 inhibition	+	0.6811	68.11%
CYP2C19 inhibition	+	0.7665	76.65%
CYP2D6 inhibition	-	0.7008	70.08%
CYP1A2 inhibition	+	0.7315	73.15%
CYP2C8 inhibition	+	0.6910	69.10%
CYP inhibitory promiscuity	+	0.6652	66.52%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.8386	83.86%
Carcinogenicity (trinary)	Non-required	0.7057	70.57%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.6042	60.42%
Skin irritation	-	0.8006	80.06%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4202	42.02%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	-	0.6325	63.25%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6710	67.10%
Acute Oral Toxicity (c)	III	0.7246	72.46%
Estrogen receptor binding	+	0.9513	95.13%
Androgen receptor binding	+	0.7420	74.20%
Thyroid receptor binding	+	0.6495	64.95%
Glucocorticoid receptor binding	+	0.9138	91.38%
Aromatase binding	+	0.7079	70.79%
PPAR gamma	+	0.8671	86.71%
Honey bee toxicity	-	0.8857	88.57%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.9972	99.72%

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	99.29%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.90%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.36%	99.17%
CHEMBL3194	P02766	Transthyretin	91.96%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.72%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.46%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.10%	98.95%
CHEMBL4208	P20618	Proteasome component C5	86.79%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	86.37%	94.73%
CHEMBL2535	P11166	Glucose transporter	84.75%	98.75%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.42%	97.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.25%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.91%	93.99%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.62%	96.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.61%	80.78%
CHEMBL340	P08684	Cytochrome P450 3A4	80.01%	91.19%

Plants that contains it

• Glycyrrhiza glabra

Cross-Links

• PubChem: 66751828
• LOTUS: LTS0208644
• wikiData: Q105234563