(E)-1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

Details

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Internal ID 972e95c9-7a86-4486-a0a1-eaea6cbebef9
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
IUPAC Name (E)-1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
SMILES (Canonical) COC1=C(C=CC(=C1)C=CC(=O)C2=C(C=C(C=C2OC3C(C(C(C(O3)CO)O)O)O)O)O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)/C=C/C(=O)C2=C(C=C(C=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O)O)O)O
InChI InChI=1S/C22H24O11/c1-31-15-6-10(2-4-12(15)25)3-5-13(26)18-14(27)7-11(24)8-16(18)32-22-21(30)20(29)19(28)17(9-23)33-22/h2-8,17,19-25,27-30H,9H2,1H3/b5-3+/t17-,19+,20-,21+,22+/m0/s1
InChI Key WYBQXABYXWDZIL-UIVZHQRXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C22H24O11
Molecular Weight 464.40 g/mol
Exact Mass 464.13186158 g/mol
Topological Polar Surface Area (TPSA) 186.00 Ų
XlogP 1.00
Atomic LogP (AlogP) -0.11
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (E)-1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)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 - 0.6070 60.70%
Caco-2 - 0.9030 90.30%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.6113 61.13%
OATP2B1 inhibitior + 0.5810 58.10%
OATP1B1 inhibitior + 0.9164 91.64%
OATP1B3 inhibitior + 0.9735 97.35%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior - 0.5300 53.00%
P-glycoprotein inhibitior - 0.6195 61.95%
P-glycoprotein substrate - 0.8083 80.83%
CYP3A4 substrate + 0.5745 57.45%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8578 85.78%
CYP3A4 inhibition - 0.8029 80.29%
CYP2C9 inhibition - 0.8622 86.22%
CYP2C19 inhibition - 0.8645 86.45%
CYP2D6 inhibition - 0.9104 91.04%
CYP1A2 inhibition - 0.8780 87.80%
CYP2C8 inhibition + 0.7732 77.32%
CYP inhibitory promiscuity - 0.5991 59.91%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.7362 73.62%
Eye corrosion - 0.9903 99.03%
Eye irritation - 0.8591 85.91%
Skin irritation - 0.8263 82.63%
Skin corrosion - 0.9545 95.45%
Ames mutagenesis - 0.6900 69.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6585 65.85%
Micronuclear + 0.5933 59.33%
Hepatotoxicity - 0.8875 88.75%
skin sensitisation - 0.8536 85.36%
Respiratory toxicity - 0.7000 70.00%
Reproductive toxicity + 0.6111 61.11%
Mitochondrial toxicity - 0.6125 61.25%
Nephrotoxicity - 0.7668 76.68%
Acute Oral Toxicity (c) III 0.7589 75.89%
Estrogen receptor binding + 0.7645 76.45%
Androgen receptor binding + 0.5539 55.39%
Thyroid receptor binding + 0.5164 51.64%
Glucocorticoid receptor binding - 0.4859 48.59%
Aromatase binding + 0.5651 56.51%
PPAR gamma + 0.6763 67.63%
Honey bee toxicity - 0.8277 82.77%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5455 54.55%
Fish aquatic toxicity + 0.8307 83.07%

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 99.43% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.64% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 95.97% 96.00%
CHEMBL3194 P02766 Transthyretin 95.81% 90.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.76% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.34% 89.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 93.81% 99.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.07% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 89.42% 94.73%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 88.86% 89.62%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 87.80% 95.50%
CHEMBL4208 P20618 Proteasome component C5 86.91% 90.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.77% 97.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 81.62% 92.94%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.57% 94.45%

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.
Acacia dealbata

Cross-Links

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PubChem 163037370
LOTUS LTS0088210
wikiData Q105322040