1-[2,4-Dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Details

Top
Internal ID d6c44d1a-8514-4c82-8def-d4cb60e5edc6
Taxonomy Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 3-prenylated chalcones
IUPAC Name 1-[2,4-dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
SMILES (Canonical) CC(=CCC1=C(C(=C(C(=C1O)C(=O)C=CC2=CC=C(C=C2)O)OC)CC=C(C)C)O)C
SMILES (Isomeric) CC(=CCC1=C(C(=C(C(=C1O)C(=O)C=CC2=CC=C(C=C2)O)OC)CC=C(C)C)O)C
InChI InChI=1S/C26H30O5/c1-16(2)6-13-20-24(29)21(14-7-17(3)4)26(31-5)23(25(20)30)22(28)15-10-18-8-11-19(27)12-9-18/h6-12,15,27,29-30H,13-14H2,1-5H3
InChI Key HOTYOZVURUOVTK-UHFFFAOYSA-N
Popularity 2 references in papers

Physical and Chemical Properties

Top
Molecular Formula C26H30O5
Molecular Weight 422.50 g/mol
Exact Mass 422.20932405 g/mol
Topological Polar Surface Area (TPSA) 87.00 Ų
XlogP 7.00
Atomic LogP (AlogP) 5.73
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 8

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of 1-[2,4-Dihydroxy-6-methoxy-3,5-bis(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 + 0.9937 99.37%
Caco-2 + 0.6009 60.09%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.8120 81.20%
OATP2B1 inhibitior - 0.5711 57.11%
OATP1B1 inhibitior + 0.8275 82.75%
OATP1B3 inhibitior + 0.8776 87.76%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.9087 90.87%
P-glycoprotein inhibitior + 0.8105 81.05%
P-glycoprotein substrate - 0.7415 74.15%
CYP3A4 substrate + 0.5202 52.02%
CYP2C9 substrate - 0.7875 78.75%
CYP2D6 substrate - 0.8322 83.22%
CYP3A4 inhibition - 0.6712 67.12%
CYP2C9 inhibition + 0.8238 82.38%
CYP2C19 inhibition + 0.9049 90.49%
CYP2D6 inhibition - 0.7020 70.20%
CYP1A2 inhibition + 0.7755 77.55%
CYP2C8 inhibition + 0.6744 67.44%
CYP inhibitory promiscuity + 0.8631 86.31%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.7916 79.16%
Carcinogenicity (trinary) Non-required 0.7686 76.86%
Eye corrosion - 0.9897 98.97%
Eye irritation + 0.6159 61.59%
Skin irritation - 0.8160 81.60%
Skin corrosion - 0.9557 95.57%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8111 81.11%
Micronuclear - 0.5700 57.00%
Hepatotoxicity - 0.6343 63.43%
skin sensitisation - 0.6648 66.48%
Respiratory toxicity - 0.6778 67.78%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.7440 74.40%
Acute Oral Toxicity (c) III 0.6824 68.24%
Estrogen receptor binding + 0.9328 93.28%
Androgen receptor binding + 0.8002 80.02%
Thyroid receptor binding + 0.6695 66.95%
Glucocorticoid receptor binding + 0.8768 87.68%
Aromatase binding + 0.7488 74.88%
PPAR gamma + 0.9034 90.34%
Honey bee toxicity - 0.8891 88.91%
Biodegradation - 0.9500 95.00%
Crustacea aquatic toxicity - 0.7055 70.55%
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 97.47% 91.11%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 93.06% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.40% 86.33%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.89% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.61% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.27% 99.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.53% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 86.13% 94.73%
CHEMBL2581 P07339 Cathepsin D 85.84% 98.95%
CHEMBL3194 P02766 Transthyretin 83.68% 90.71%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.10% 95.50%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 82.49% 91.71%

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 25201207
LOTUS LTS0002181
wikiData Q105031534