2-Propen-1-one, 1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(2,4-dihydroxyphenyl)-, (E)-; (2E)-1-[2,4-Dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(2,4-dihydroxyphenyl)-2-propen-1-one

Details

• Internal ID: 6e97ffb6-1030-4632-9a88-3ac9482b6050
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 3-prenylated chalcones
• IUPAC Name: 1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-(2,4-dihydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=C(C=C(C=C2)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=C(C=C(C=C2)O)O)O)C
• InChI: InChI=1S/C20H20O5/c1-12(2)3-7-15-18(23)10-8-16(20(15)25)17(22)9-5-13-4-6-14(21)11-19(13)24/h3-6,8-11,21,23-25H,7H2,1-2H3
• InChI Key: NXBYIJSAISXPKJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.13107373 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 3.91
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 2-Propen-1-one, 1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(2,4-dihydroxyphenyl)-, (E)-; (2E)-1-[2,4-Dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-3-(2,4-dihydroxyphenyl)-2-propen-1-one
• AKOS032962443
• 2,4,2',4'-tetrahydroxy-3'-prenylchalcone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.6757	67.57%
Blood Brain Barrier	-	0.5379	53.79%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8210	82.10%
OATP2B1 inhibitior	+	0.5727	57.27%
OATP1B1 inhibitior	+	0.8368	83.68%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9588	95.88%
BSEP inhibitior	+	0.8727	87.27%
P-glycoprotein inhibitior	-	0.6321	63.21%
P-glycoprotein substrate	-	0.7488	74.88%
CYP3A4 substrate	-	0.5084	50.84%
CYP2C9 substrate	-	0.7861	78.61%
CYP2D6 substrate	-	0.8509	85.09%
CYP3A4 inhibition	+	0.5800	58.00%
CYP2C9 inhibition	+	0.9411	94.11%
CYP2C19 inhibition	+	0.9399	93.99%
CYP2D6 inhibition	-	0.6694	66.94%
CYP1A2 inhibition	+	0.9454	94.54%
CYP2C8 inhibition	+	0.6017	60.17%
CYP inhibitory promiscuity	+	0.9305	93.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7972	79.72%
Carcinogenicity (trinary)	Non-required	0.7738	77.38%
Eye corrosion	-	0.9868	98.68%
Eye irritation	+	0.6317	63.17%
Skin irritation	-	0.7357	73.57%
Skin corrosion	-	0.8191	81.91%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5685	56.85%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.5322	53.22%
skin sensitisation	+	0.6932	69.32%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7029	70.29%
Acute Oral Toxicity (c)	III	0.7270	72.70%
Estrogen receptor binding	+	0.9743	97.43%
Androgen receptor binding	+	0.7992	79.92%
Thyroid receptor binding	+	0.7235	72.35%
Glucocorticoid receptor binding	+	0.9309	93.09%
Aromatase binding	+	0.7921	79.21%
PPAR gamma	+	0.9276	92.76%
Honey bee toxicity	-	0.9005	90.05%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1973	P14679	Tyrosinase	80 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.10%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.12%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.24%	94.73%
CHEMBL3194	P02766	Transthyretin	92.12%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.38%	86.33%
CHEMBL4208	P20618	Proteasome component C5	88.20%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.12%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.57%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.32%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.98%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.47%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.08%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.00%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.71%	95.50%

Plants that contains it

• Artocarpus integer
• Broussonetia papyrifera
• Glycyrrhiza glabra
• Maclura pomifera
• Morus alba
• Morus mesozygia
• Morus nigra

Cross-Links

• PubChem: 69906284
• LOTUS: LTS0041150
• wikiData: Q105186931