xanthohumol E

Details

• Internal ID: df9703a1-b29c-4c31-b5c5-3ac4779d7040
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 3-prenylated chalcones
• IUPAC Name: (E)-1-[5,7-dihydroxy-2,2-dimethyl-6-(3-methylbut-2-enyl)chromen-8-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): CC(=CCC1=C(C(=C2C(=C1O)C=CC(O2)(C)C)C(=O)C=CC3=CC=C(C=C3)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=C2C(=C1O)C=CC(O2)(C)C)C(=O)/C=C/C3=CC=C(C=C3)O)O)C
• InChI: InChI=1S/C25H26O5/c1-15(2)5-11-18-22(28)19-13-14-25(3,4)30-24(19)21(23(18)29)20(27)12-8-16-6-9-17(26)10-7-16/h5-10,12-14,26,28-29H,11H2,1-4H3/b12-8+
• InChI Key: KRZGSPKDWYNTHE-XYOKQWHBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₅
• Molecular Weight: 406.50 g/mol
• Exact Mass: 406.17802393 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 5.39
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 3'-Prenyl-6'',6''-dimethylpyrano[2'',3'':6',5']-4,2',4'-trihydroxychalcone
• SCHEMBL15704298
• CHEBI:175258
• LMPK12120263
• (E)-1-[5,7-dihydroxy-2,2-dimethyl-6-(3-methylbut-2-enyl)chromen-8-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	-	0.5911	59.11%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6754	67.54%
OATP2B1 inhibitior	-	0.5737	57.37%
OATP1B1 inhibitior	+	0.7767	77.67%
OATP1B3 inhibitior	+	0.9394	93.94%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9649	96.49%
P-glycoprotein inhibitior	+	0.7475	74.75%
P-glycoprotein substrate	-	0.5766	57.66%
CYP3A4 substrate	+	0.5975	59.75%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8304	83.04%
CYP3A4 inhibition	-	0.7581	75.81%
CYP2C9 inhibition	+	0.8468	84.68%
CYP2C19 inhibition	+	0.8691	86.91%
CYP2D6 inhibition	-	0.8013	80.13%
CYP1A2 inhibition	+	0.8795	87.95%
CYP2C8 inhibition	+	0.6742	67.42%
CYP inhibitory promiscuity	+	0.8729	87.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7003	70.03%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.5547	55.47%
Skin irritation	-	0.7033	70.33%
Skin corrosion	-	0.9187	91.87%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8217	82.17%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.6843	68.43%
skin sensitisation	-	0.6463	64.63%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6725	67.25%
Acute Oral Toxicity (c)	III	0.6869	68.69%
Estrogen receptor binding	+	0.9611	96.11%
Androgen receptor binding	+	0.8299	82.99%
Thyroid receptor binding	+	0.7642	76.42%
Glucocorticoid receptor binding	+	0.9016	90.16%
Aromatase binding	+	0.7494	74.94%
PPAR gamma	+	0.8870	88.70%
Honey bee toxicity	-	0.8495	84.95%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9929	99.29%

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	99.01%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.47%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.79%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.79%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.26%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.50%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	89.35%	93.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.01%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.77%	85.14%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	87.76%	89.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.72%	96.00%
CHEMBL4208	P20618	Proteasome component C5	84.38%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.77%	99.17%

Plants that contains it

• Alkanna cappadocica
• Artemisia rupestris subsp. rupestris
• Atalantia racemosa
• Buddleja cordata
• Crambe tatarica
• Diospyros eriantha
• Fritillaria monantha
• Hoffmannia strigillosa
• Humulus lupulus
• Millettia erythrocalyx
• Myrsine lancifolia
• Ononis vaginalis
• Pteris semipinnata
• Salvia hispanica
• Scorzonera pseudodivaricata
• Stenocereus griseus
• Syncarpia hillii

Cross-Links

• PubChem: 25245324
• NPASS: NPC91494
• LOTUS: LTS0133231
• wikiData: Q105145313