(E)-1-[3-[(2R)-2,3-dihydroxy-3-methylbutyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Details

• Internal ID: eda76b97-623c-44bd-9a78-3863fd3b9f7b
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 3-prenylated chalcones
• IUPAC Name: (E)-1-[3-[(2R)-2,3-dihydroxy-3-methylbutyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): CC(C)(C(CC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)O)O)O
• SMILES (Isomeric): CC(C)([C@@H](CC1=C(C=CC(=C1O)C(=O)/C=C/C2=CC=C(C=C2)O)O)O)O
• InChI: InChI=1S/C20H22O6/c1-20(2,26)18(24)11-15-17(23)10-8-14(19(15)25)16(22)9-5-12-3-6-13(21)7-4-12/h3-10,18,21,23-26H,11H2,1-2H3/b9-5+/t18-/m1/s1
• InChI Key: QZJFVTLIVWFNNF-QKYXPGDISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.14163842 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9879	98.79%
Caco-2	-	0.5574	55.74%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7665	76.65%
OATP2B1 inhibitior	+	0.5694	56.94%
OATP1B1 inhibitior	+	0.8662	86.62%
OATP1B3 inhibitior	+	0.9630	96.30%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8838	88.38%
BSEP inhibitior	+	0.7970	79.70%
P-glycoprotein inhibitior	-	0.6900	69.00%
P-glycoprotein substrate	-	0.7999	79.99%
CYP3A4 substrate	-	0.5158	51.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8554	85.54%
CYP3A4 inhibition	-	0.6116	61.16%
CYP2C9 inhibition	-	0.6849	68.49%
CYP2C19 inhibition	-	0.7553	75.53%
CYP2D6 inhibition	-	0.8589	85.89%
CYP1A2 inhibition	+	0.5169	51.69%
CYP2C8 inhibition	+	0.6265	62.65%
CYP inhibitory promiscuity	-	0.7539	75.39%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6845	68.45%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.6961	69.61%
Skin irritation	-	0.7032	70.32%
Skin corrosion	-	0.7138	71.38%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4889	48.89%
Micronuclear	-	0.5782	57.82%
Hepatotoxicity	-	0.6801	68.01%
skin sensitisation	+	0.6380	63.80%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7558	75.58%
Acute Oral Toxicity (c)	III	0.7977	79.77%
Estrogen receptor binding	+	0.9069	90.69%
Androgen receptor binding	+	0.7489	74.89%
Thyroid receptor binding	+	0.7299	72.99%
Glucocorticoid receptor binding	+	0.8787	87.87%
Aromatase binding	+	0.7191	71.91%
PPAR gamma	+	0.8707	87.07%
Honey bee toxicity	-	0.8757	87.57%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9906	99.06%

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%
CHEMBL2581	P07339	Cathepsin D	95.74%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.64%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.54%	94.73%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	89.26%	90.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.20%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.46%	96.09%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	86.34%	100.00%
CHEMBL3194	P02766	Transthyretin	85.99%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.55%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.50%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.60%	94.45%

Plants that contains it

• Brosimum acutifolium

Cross-Links

• PubChem: 163188343
• LOTUS: LTS0111373
• wikiData: Q105232100