Xanthohumol B

Details

• Internal ID: 1929764c-02de-4584-84b3-eb1a6ebaa0f5
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: (E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): CC1(C(CC2=C(C(=C(C=C2O1)OC)C(=O)C=CC3=CC=C(C=C3)O)O)O)C
• SMILES (Isomeric): CC1(C(CC2=C(C(=C(C=C2O1)OC)C(=O)/C=C/C3=CC=C(C=C3)O)O)O)C
• InChI: InChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+
• InChI Key: GUQGMEWOCKDLDE-RMKNXTFCSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.14163842 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.08
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• Dehydrocycloxanthohumol hydrate
• 189308-10-9
• CHEBI:66334
• (E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• 6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalcone
• 2-Propen-1-one, 1-(3,4-dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-3-(4-hydroxyphenyl)-, (2E)-
• CHEMBL520430
• SCHEMBL12961703
• DTXSID301317586
• LMPK12120299
• AKOS040735479
• Q27134882
• (2E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• rac-(E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• rac-6'',6''-Dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalcone
• rac-6-[3,4-dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-benzo[b]pyrano]-3-(4-hydroxyphenyl)-2-propen-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9931	99.31%
Caco-2	+	0.6546	65.46%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5876	58.76%
OATP2B1 inhibitior	-	0.5774	57.74%
OATP1B1 inhibitior	+	0.8742	87.42%
OATP1B3 inhibitior	+	0.9603	96.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9011	90.11%
P-glycoprotein inhibitior	+	0.5729	57.29%
P-glycoprotein substrate	-	0.6366	63.66%
CYP3A4 substrate	+	0.6342	63.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8224	82.24%
CYP3A4 inhibition	-	0.7103	71.03%
CYP2C9 inhibition	-	0.9038	90.38%
CYP2C19 inhibition	-	0.6020	60.20%
CYP2D6 inhibition	-	0.7052	70.52%
CYP1A2 inhibition	+	0.7291	72.91%
CYP2C8 inhibition	+	0.8643	86.43%
CYP inhibitory promiscuity	-	0.7812	78.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5887	58.87%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.6500	65.00%
Skin irritation	-	0.7502	75.02%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4058	40.58%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	-	0.6966	69.66%
skin sensitisation	-	0.8101	81.01%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5606	56.06%
Acute Oral Toxicity (c)	III	0.6125	61.25%
Estrogen receptor binding	+	0.9035	90.35%
Androgen receptor binding	+	0.7183	71.83%
Thyroid receptor binding	+	0.7152	71.52%
Glucocorticoid receptor binding	+	0.8340	83.40%
Aromatase binding	+	0.7185	71.85%
PPAR gamma	+	0.8048	80.48%
Honey bee toxicity	-	0.7961	79.61%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.9451	94.51%

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	99.52%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.27%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.01%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.60%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.40%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.18%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	91.64%	89.67%
CHEMBL3194	P02766	Transthyretin	91.57%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.36%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.24%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.94%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.56%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.52%	92.94%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	86.07%	89.44%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.17%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.48%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.46%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.34%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.32%	85.14%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.81%	89.50%
CHEMBL4208	P20618	Proteasome component C5	82.15%	90.00%
CHEMBL2535	P11166	Glucose transporter	81.69%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.61%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	81.23%	91.19%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 9799506
• NPASS: NPC263384
• ChEMBL: CHEMBL520430
• LOTUS: LTS0026879
• wikiData: Q27134882