1-[2-Hydroxy-4,6-dimethoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Details

Top
Internal ID 6ac8e804-54b4-4066-8eb1-9fef22b47bd8
Taxonomy Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 3-prenylated chalcones
IUPAC Name 1-[2-hydroxy-4,6-dimethoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
SMILES (Canonical) CC(=CCC1=C(C(=C(C=C1OC)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C
SMILES (Isomeric) CC(=CCC1=C(C(=C(C=C1OC)OC)C(=O)C=CC2=CC=C(C=C2)O)O)C
InChI InChI=1S/C22H24O5/c1-14(2)5-11-17-19(26-3)13-20(27-4)21(22(17)25)18(24)12-8-15-6-9-16(23)10-7-15/h5-10,12-13,23,25H,11H2,1-4H3
InChI Key UVBDKJHYMQEAQV-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C22H24O5
Molecular Weight 368.40 g/mol
Exact Mass 368.16237386 g/mol
Topological Polar Surface Area (TPSA) 76.00 Ų
XlogP 5.40
Atomic LogP (AlogP) 4.52
H-Bond Acceptor 5
H-Bond Donor 2
Rotatable Bonds 7

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of 1-[2-Hydroxy-4,6-dimethoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9966 99.66%
Caco-2 + 0.8220 82.20%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.8411 84.11%
OATP2B1 inhibitior - 0.8628 86.28%
OATP1B1 inhibitior + 0.8349 83.49%
OATP1B3 inhibitior + 0.8765 87.65%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.9013 90.13%
P-glycoprotein inhibitior + 0.8620 86.20%
P-glycoprotein substrate - 0.6663 66.63%
CYP3A4 substrate + 0.5341 53.41%
CYP2C9 substrate - 0.7875 78.75%
CYP2D6 substrate - 0.8322 83.22%
CYP3A4 inhibition - 0.7696 76.96%
CYP2C9 inhibition + 0.7745 77.45%
CYP2C19 inhibition + 0.9187 91.87%
CYP2D6 inhibition - 0.6910 69.10%
CYP1A2 inhibition + 0.7982 79.82%
CYP2C8 inhibition + 0.8240 82.40%
CYP inhibitory promiscuity + 0.8717 87.17%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.7249 72.49%
Carcinogenicity (trinary) Non-required 0.7202 72.02%
Eye corrosion - 0.9913 99.13%
Eye irritation + 0.6068 60.68%
Skin irritation - 0.8239 82.39%
Skin corrosion - 0.9732 97.32%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4073 40.73%
Micronuclear - 0.5700 57.00%
Hepatotoxicity - 0.6468 64.68%
skin sensitisation - 0.6723 67.23%
Respiratory toxicity - 0.7222 72.22%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity - 0.6125 61.25%
Nephrotoxicity - 0.7096 70.96%
Acute Oral Toxicity (c) III 0.7103 71.03%
Estrogen receptor binding + 0.9214 92.14%
Androgen receptor binding + 0.8062 80.62%
Thyroid receptor binding + 0.7051 70.51%
Glucocorticoid receptor binding + 0.8483 84.83%
Aromatase binding + 0.7403 74.03%
PPAR gamma + 0.8838 88.38%
Honey bee toxicity - 0.8522 85.22%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6355 63.55%
Fish aquatic toxicity + 1.0000 100.00%

Targets

Top

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 97.65% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.06% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 94.89% 96.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.21% 96.09%
CHEMBL3194 P02766 Transthyretin 92.13% 90.71%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.83% 99.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.47% 94.45%
CHEMBL2581 P07339 Cathepsin D 88.37% 98.95%
CHEMBL4208 P20618 Proteasome component C5 87.14% 90.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 86.28% 89.62%
CHEMBL3401 O75469 Pregnane X receptor 85.39% 94.73%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.94% 95.50%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 84.28% 95.56%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 84.01% 93.10%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.58% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.71% 89.00%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 82.37% 91.71%
CHEMBL3192 Q9BY41 Histone deacetylase 8 82.18% 93.99%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.51% 97.21%
CHEMBL2535 P11166 Glucose transporter 80.44% 98.75%
CHEMBL2413 P32246 C-C chemokine receptor type 1 80.34% 89.50%

Plants that contains it

Top
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

Top
PubChem 25201031
LOTUS LTS0060268
wikiData Q105279720