[(2R,3R)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl] acetate

Details

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Internal ID fc3d4523-4780-4d2b-9ed0-94bd05c55675
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
IUPAC Name [(2R,3R)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl] acetate
SMILES (Canonical) CC(=CCC1=C(C2=C(C=C1O)OC(C(C2=O)OC(=O)C)C3=CC=CC=C3)O)C
SMILES (Isomeric) CC(=CCC1=C(C2=C(C=C1O)O[C@@H]([C@H](C2=O)OC(=O)C)C3=CC=CC=C3)O)C
InChI InChI=1S/C22H22O6/c1-12(2)9-10-15-16(24)11-17-18(19(15)25)20(26)22(27-13(3)23)21(28-17)14-7-5-4-6-8-14/h4-9,11,21-22,24-25H,10H2,1-3H3/t21-,22+/m1/s1
InChI Key PBDWJKUJWZPHNK-YADHBBJMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H22O6
Molecular Weight 382.40 g/mol
Exact Mass 382.14163842 g/mol
Topological Polar Surface Area (TPSA) 93.10 Ų
XlogP 4.70
Atomic LogP (AlogP) 3.85
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3R)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9698 96.98%
Caco-2 - 0.6539 65.39%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.6200 62.00%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8199 81.99%
OATP1B3 inhibitior - 0.2802 28.02%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8203 82.03%
P-glycoprotein inhibitior + 0.7101 71.01%
P-glycoprotein substrate - 0.8547 85.47%
CYP3A4 substrate + 0.5543 55.43%
CYP2C9 substrate - 0.5800 58.00%
CYP2D6 substrate - 0.8474 84.74%
CYP3A4 inhibition - 0.8893 88.93%
CYP2C9 inhibition + 0.7969 79.69%
CYP2C19 inhibition + 0.7063 70.63%
CYP2D6 inhibition - 0.7755 77.55%
CYP1A2 inhibition - 0.5000 50.00%
CYP2C8 inhibition + 0.5257 52.57%
CYP inhibitory promiscuity + 0.7567 75.67%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6190 61.90%
Eye corrosion - 0.9905 99.05%
Eye irritation - 0.7305 73.05%
Skin irritation - 0.7563 75.63%
Skin corrosion - 0.9453 94.53%
Ames mutagenesis + 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3633 36.33%
Micronuclear + 0.5500 55.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.8177 81.77%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.7750 77.50%
Nephrotoxicity - 0.6688 66.88%
Acute Oral Toxicity (c) III 0.6317 63.17%
Estrogen receptor binding + 0.8873 88.73%
Androgen receptor binding + 0.6869 68.69%
Thyroid receptor binding - 0.5170 51.70%
Glucocorticoid receptor binding + 0.8267 82.67%
Aromatase binding - 0.5754 57.54%
PPAR gamma + 0.8283 82.83%
Honey bee toxicity - 0.8589 85.89%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 0.9973 99.73%

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 99.61% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 96.41% 91.49%
CHEMBL2581 P07339 Cathepsin D 95.19% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.26% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.47% 94.45%
CHEMBL3401 O75469 Pregnane X receptor 91.32% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.94% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.02% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.61% 96.09%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 87.08% 94.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.07% 89.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.07% 99.17%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 83.98% 95.64%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.50% 85.14%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 80.37% 96.95%

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.
Helichrysum thapsus

Cross-Links

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PubChem 162937917
LOTUS LTS0053767
wikiData Q105205105