3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

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Internal ID e8cbaa0a-c006-492e-aa00-681661385458
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
IUPAC Name 3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical) CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O)C
SMILES (Isomeric) CC(=CCC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C
InChI InChI=1S/C26H28O11/c1-11(2)3-8-14-16(35-26-23(34)21(32)19(30)17(10-27)36-26)9-15(29)18-20(31)22(33)24(37-25(14)18)12-4-6-13(28)7-5-12/h3-7,9,17,19,21,23,26-30,32-34H,8,10H2,1-2H3/t17-,19-,21+,23-,26-/m1/s1
InChI Key FJSOHLNMRNSYFR-RGLOOMPQSA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C26H28O11
Molecular Weight 516.50 g/mol
Exact Mass 516.16316171 g/mol
Topological Polar Surface Area (TPSA) 186.00 Ų
XlogP 2.60
Atomic LogP (AlogP) 1.26
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8617 86.17%
Caco-2 - 0.9069 90.69%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.7385 73.85%
OATP2B1 inhibitior - 0.5522 55.22%
OATP1B1 inhibitior + 0.8738 87.38%
OATP1B3 inhibitior + 0.9560 95.60%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.9012 90.12%
P-glycoprotein inhibitior - 0.4419 44.19%
P-glycoprotein substrate - 0.6269 62.69%
CYP3A4 substrate + 0.6338 63.38%
CYP2C9 substrate - 0.6532 65.32%
CYP2D6 substrate - 0.8528 85.28%
CYP3A4 inhibition - 0.9110 91.10%
CYP2C9 inhibition - 0.7009 70.09%
CYP2C19 inhibition - 0.6690 66.90%
CYP2D6 inhibition - 0.8119 81.19%
CYP1A2 inhibition - 0.6196 61.96%
CYP2C8 inhibition + 0.7466 74.66%
CYP inhibitory promiscuity + 0.5495 54.95%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7563 75.63%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9001 90.01%
Skin irritation - 0.7961 79.61%
Skin corrosion - 0.9458 94.58%
Ames mutagenesis + 0.5809 58.09%
Human Ether-a-go-go-Related Gene inhibition - 0.3717 37.17%
Micronuclear - 0.5267 52.67%
Hepatotoxicity - 0.6038 60.38%
skin sensitisation - 0.8585 85.85%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity - 0.5375 53.75%
Nephrotoxicity - 0.6604 66.04%
Acute Oral Toxicity (c) III 0.5863 58.63%
Estrogen receptor binding + 0.7914 79.14%
Androgen receptor binding + 0.7073 70.73%
Thyroid receptor binding - 0.4890 48.90%
Glucocorticoid receptor binding + 0.6307 63.07%
Aromatase binding + 0.6289 62.89%
PPAR gamma + 0.7593 75.93%
Honey bee toxicity - 0.7109 71.09%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9824 98.24%

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 99.73% 91.11%
CHEMBL2581 P07339 Cathepsin D 97.35% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.07% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 95.49% 94.73%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.39% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.18% 94.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.42% 99.17%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 91.48% 95.64%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.93% 86.33%
CHEMBL1951 P21397 Monoamine oxidase A 89.47% 91.49%
CHEMBL3194 P02766 Transthyretin 87.06% 90.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.03% 95.56%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.80% 99.15%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 85.35% 91.71%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 85.25% 95.78%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.70% 95.89%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 84.10% 86.92%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 82.53% 96.95%
CHEMBL2107 P61073 C-X-C chemokine receptor type 4 81.35% 93.10%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.10% 99.23%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.03% 96.00%

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.
Epimedium brevicornu
Epimedium grandiflorum
Epimedium koreanum
Epimedium pubescens
Epimedium sagittatum
Epimedium sempervirens
Epimedium wushanense
Phellodendron amurense
Phellodendron chinense var. glabriusculum
Tetradium ruticarpum

Cross-Links

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PubChem 14756216
NPASS NPC103264
LOTUS LTS0189240
wikiData Q104996305