1-[4,6-Dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Details

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Internal ID 0a569ce8-9e90-4184-af77-39d4ce6ca7cc
Taxonomy Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Furanochalcones
IUPAC Name 1-[4,6-dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one
SMILES (Canonical) CC(C)(C1CC2=C(O1)C=C(C(=C2O)C(=O)C=CC3=CC=C(C=C3)O)O)O
SMILES (Isomeric) CC(C)(C1CC2=C(O1)C=C(C(=C2O)C(=O)C=CC3=CC=C(C=C3)O)O)O
InChI InChI=1S/C20H20O6/c1-20(2,25)17-9-13-16(26-17)10-15(23)18(19(13)24)14(22)8-5-11-3-6-12(21)7-4-11/h3-8,10,17,21,23-25H,9H2,1-2H3
InChI Key CVUMBCAEYKOWBS-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H20O6
Molecular Weight 356.40 g/mol
Exact Mass 356.12598835 g/mol
Topological Polar Surface Area (TPSA) 107.00 Ų
XlogP 3.20
Atomic LogP (AlogP) 2.77
H-Bond Acceptor 6
H-Bond Donor 4
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 1-[4,6-Dihydroxy-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-yl]-3-(4-hydroxyphenyl)prop-2-en-1-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9941 99.41%
Caco-2 - 0.6255 62.55%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.6816 68.16%
OATP2B1 inhibitior + 0.5641 56.41%
OATP1B1 inhibitior + 0.8685 86.85%
OATP1B3 inhibitior + 0.9406 94.06%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.7195 71.95%
P-glycoprotein inhibitior - 0.5765 57.65%
P-glycoprotein substrate - 0.7477 74.77%
CYP3A4 substrate + 0.5528 55.28%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8430 84.30%
CYP3A4 inhibition - 0.5797 57.97%
CYP2C9 inhibition + 0.5000 50.00%
CYP2C19 inhibition - 0.5876 58.76%
CYP2D6 inhibition - 0.7827 78.27%
CYP1A2 inhibition + 0.7869 78.69%
CYP2C8 inhibition + 0.7180 71.80%
CYP inhibitory promiscuity + 0.6983 69.83%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4895 48.95%
Eye corrosion - 0.9907 99.07%
Eye irritation + 0.5251 52.51%
Skin irritation - 0.6775 67.75%
Skin corrosion - 0.8483 84.83%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5086 50.86%
Micronuclear + 0.5659 56.59%
Hepatotoxicity - 0.6903 69.03%
skin sensitisation - 0.6322 63.22%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity - 0.7830 78.30%
Acute Oral Toxicity (c) III 0.6120 61.20%
Estrogen receptor binding + 0.8949 89.49%
Androgen receptor binding + 0.7193 71.93%
Thyroid receptor binding + 0.7077 70.77%
Glucocorticoid receptor binding + 0.7415 74.15%
Aromatase binding + 0.7943 79.43%
PPAR gamma + 0.8750 87.50%
Honey bee toxicity - 0.9026 90.26%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5600 56.00%
Fish aquatic toxicity + 0.9885 98.85%

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 99.24% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.48% 86.33%
CHEMBL3194 P02766 Transthyretin 93.43% 90.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.21% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.89% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 90.13% 94.73%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.76% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.73% 97.09%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 86.83% 90.93%
CHEMBL242 Q92731 Estrogen receptor beta 85.81% 98.35%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 85.57% 85.00%
CHEMBL2581 P07339 Cathepsin D 84.52% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.01% 99.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 82.47% 96.09%
CHEMBL206 P03372 Estrogen receptor alpha 81.47% 97.64%
CHEMBL1951 P21397 Monoamine oxidase A 80.58% 91.49%

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 72816330
LOTUS LTS0104400
wikiData Q104971023