Xanthohumol I

Details

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Internal ID 12b4cfb0-da9c-4468-9047-1904ad02957c
Taxonomy Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
IUPAC Name (E)-1-[4-hydroxy-2-(2-hydroxypropan-2-yl)-6-methoxy-2,3-dihydro-1-benzofuran-7-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one
SMILES (Canonical) CC(C)(C1CC2=C(O1)C(=C(C=C2O)OC)C(=O)C=CC3=CC=C(C=C3)O)O
SMILES (Isomeric) CC(C)(C1CC2=C(O1)C(=C(C=C2O)OC)C(=O)/C=C/C3=CC=C(C=C3)O)O
InChI InChI=1S/C21H22O6/c1-21(2,25)18-10-14-16(24)11-17(26-3)19(20(14)27-18)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 PUJSPQKGZNTZCR-RMKNXTFCSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H22O6
Molecular Weight 370.40 g/mol
Exact Mass 370.14163842 g/mol
Topological Polar Surface Area (TPSA) 96.20 Ų
XlogP 3.00
Atomic LogP (AlogP) 3.08
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 5

Synonyms

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688360-06-7
HY-N10917
AKOS040734513
CS-0637566

2D Structure

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2D Structure of Xanthohumol I

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9965 99.65%
Caco-2 + 0.6647 66.47%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.7118 71.18%
OATP2B1 inhibitior - 0.7190 71.90%
OATP1B1 inhibitior + 0.8854 88.54%
OATP1B3 inhibitior + 0.9236 92.36%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8223 82.23%
P-glycoprotein inhibitior - 0.4853 48.53%
P-glycoprotein substrate - 0.6695 66.95%
CYP3A4 substrate + 0.6077 60.77%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8043 80.43%
CYP3A4 inhibition - 0.6021 60.21%
CYP2C9 inhibition - 0.6756 67.56%
CYP2C19 inhibition + 0.5453 54.53%
CYP2D6 inhibition - 0.7634 76.34%
CYP1A2 inhibition + 0.7033 70.33%
CYP2C8 inhibition + 0.8387 83.87%
CYP inhibitory promiscuity + 0.6203 62.03%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4232 42.32%
Eye corrosion - 0.9910 99.10%
Eye irritation - 0.5558 55.58%
Skin irritation - 0.7666 76.66%
Skin corrosion - 0.9389 93.89%
Ames mutagenesis - 0.6454 64.54%
Human Ether-a-go-go-Related Gene inhibition - 0.3829 38.29%
Micronuclear + 0.5259 52.59%
Hepatotoxicity - 0.6343 63.43%
skin sensitisation - 0.7755 77.55%
Respiratory toxicity - 0.5222 52.22%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity - 0.6774 67.74%
Acute Oral Toxicity (c) III 0.5311 53.11%
Estrogen receptor binding + 0.8963 89.63%
Androgen receptor binding + 0.6878 68.78%
Thyroid receptor binding + 0.7487 74.87%
Glucocorticoid receptor binding + 0.8244 82.44%
Aromatase binding + 0.7557 75.57%
PPAR gamma + 0.8551 85.51%
Honey bee toxicity - 0.8399 83.99%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9850 98.50%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 98.78% 91.11%
CHEMBL3194 P02766 Transthyretin 96.36% 90.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.07% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.89% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.92% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.22% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.13% 99.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.49% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.77% 97.09%
CHEMBL2535 P11166 Glucose transporter 86.69% 98.75%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 86.47% 96.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 85.08% 89.62%
CHEMBL3401 O75469 Pregnane X receptor 84.86% 94.73%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.09% 92.94%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.40% 89.50%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 82.34% 90.93%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 82.20% 95.78%
CHEMBL340 P08684 Cytochrome P450 3A4 81.82% 91.19%
CHEMBL4208 P20618 Proteasome component C5 80.83% 90.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 80.82% 93.99%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.80% 95.89%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Humulus lupulus

Cross-Links

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PubChem 12986068
LOTUS LTS0062666
wikiData Q105215136