5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-methoxy-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 fa3d4aa4-a27e-4b91-9641-93903ec6fb72
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
IUPAC Name 5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical) COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)OC)O
SMILES (Isomeric) COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)OC)O
InChI InChI=1S/C23H24O13/c1-32-10-5-8(3-4-9(10)25)21-22(33-2)18(29)14-11(34-21)6-12(15(26)17(14)28)35-23-20(31)19(30)16(27)13(7-24)36-23/h3-6,13,16,19-20,23-28,30-31H,7H2,1-2H3/t13-,16-,19+,20-,23-/m1/s1
InChI Key RCEFANLBVZSGRB-ZZZLWRASSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H24O13
Molecular Weight 508.40 g/mol
Exact Mass 508.12169082 g/mol
Topological Polar Surface Area (TPSA) 205.00 Ų
XlogP 0.70
Atomic LogP (AlogP) -0.23
H-Bond Acceptor 13
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 5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-methoxy-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 - 0.5074 50.74%
Caco-2 - 0.9094 90.94%
Blood Brain Barrier - 0.9000 90.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.6238 62.38%
OATP2B1 inhibitior - 0.5512 55.12%
OATP1B1 inhibitior + 0.9186 91.86%
OATP1B3 inhibitior + 0.9678 96.78%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.4670 46.70%
P-glycoprotein inhibitior - 0.5894 58.94%
P-glycoprotein substrate - 0.6706 67.06%
CYP3A4 substrate + 0.6175 61.75%
CYP2C9 substrate - 0.8415 84.15%
CYP2D6 substrate - 0.8515 85.15%
CYP3A4 inhibition - 0.8862 88.62%
CYP2C9 inhibition - 0.9258 92.58%
CYP2C19 inhibition - 0.9329 93.29%
CYP2D6 inhibition - 0.9457 94.57%
CYP1A2 inhibition - 0.9089 90.89%
CYP2C8 inhibition + 0.8146 81.46%
CYP inhibitory promiscuity - 0.7195 71.95%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7238 72.38%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9082 90.82%
Skin irritation - 0.8305 83.05%
Skin corrosion - 0.9609 96.09%
Ames mutagenesis - 0.5492 54.92%
Human Ether-a-go-go-Related Gene inhibition - 0.4032 40.32%
Micronuclear + 0.6733 67.33%
Hepatotoxicity - 0.7000 70.00%
skin sensitisation - 0.9389 93.89%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.9323 93.23%
Acute Oral Toxicity (c) III 0.6799 67.99%
Estrogen receptor binding + 0.8507 85.07%
Androgen receptor binding + 0.6310 63.10%
Thyroid receptor binding + 0.5421 54.21%
Glucocorticoid receptor binding + 0.6860 68.60%
Aromatase binding + 0.6100 61.00%
PPAR gamma + 0.7077 70.77%
Honey bee toxicity - 0.7645 76.45%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5849 58.49%
Fish aquatic toxicity + 0.7522 75.22%

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 99.10% 91.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 97.75% 94.00%
CHEMBL2581 P07339 Cathepsin D 96.32% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.84% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.82% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.17% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.12% 85.14%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.64% 99.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.97% 94.45%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 88.23% 99.15%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 88.15% 86.92%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 87.37% 95.64%
CHEMBL3401 O75469 Pregnane X receptor 86.77% 94.73%
CHEMBL220 P22303 Acetylcholinesterase 86.51% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.29% 95.56%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 84.98% 96.21%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.38% 95.89%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.01% 96.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.07% 90.71%

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.
Clibadium terebinthinaceum

Cross-Links

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PubChem 163045427
LOTUS LTS0244884
wikiData Q105233569