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

Details

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Internal ID 3fb9f23c-f91b-4e12-b2f4-1550102e00db
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
IUPAC Name 2-(3,4-dihydroxyphenyl)-5,8-dihydroxy-7-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical) COC1=C(C2=C(C(=C1)O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
SMILES (Isomeric) COC1=C(C2=C(C(=C1)O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
InChI InChI=1S/C22H22O13/c1-32-11-5-10(26)13-16(29)21(35-22-18(31)17(30)14(27)12(6-23)33-22)19(34-20(13)15(11)28)7-2-3-8(24)9(25)4-7/h2-5,12,14,17-18,22-28,30-31H,6H2,1H3/t12-,14-,17+,18-,22+/m1/s1
InChI Key XHJUTGOKRFRRGS-OOVDEOTFSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H22O13
Molecular Weight 494.40 g/mol
Exact Mass 494.10604075 g/mol
Topological Polar Surface Area (TPSA) 216.00 Ų
XlogP 0.30
Atomic LogP (AlogP) -0.53
H-Bond Acceptor 13
H-Bond Donor 8
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 2-(3,4-dihydroxyphenyl)-5,8-dihydroxy-7-methoxy-3-[(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 - 0.4855 48.55%
Caco-2 - 0.8732 87.32%
Blood Brain Barrier - 0.8500 85.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.6190 61.90%
OATP2B1 inhibitior + 0.5877 58.77%
OATP1B1 inhibitior + 0.9197 91.97%
OATP1B3 inhibitior + 0.9740 97.40%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior - 0.7132 71.32%
P-glycoprotein inhibitior - 0.5651 56.51%
P-glycoprotein substrate - 0.6809 68.09%
CYP3A4 substrate + 0.6153 61.53%
CYP2C9 substrate - 0.8415 84.15%
CYP2D6 substrate - 0.8515 85.15%
CYP3A4 inhibition - 0.9108 91.08%
CYP2C9 inhibition - 0.9071 90.71%
CYP2C19 inhibition - 0.9173 91.73%
CYP2D6 inhibition - 0.9514 95.14%
CYP1A2 inhibition - 0.9045 90.45%
CYP2C8 inhibition + 0.7418 74.18%
CYP inhibitory promiscuity - 0.7292 72.92%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6890 68.90%
Eye corrosion - 0.9896 98.96%
Eye irritation - 0.8274 82.74%
Skin irritation - 0.8153 81.53%
Skin corrosion - 0.9600 96.00%
Ames mutagenesis + 0.6363 63.63%
Human Ether-a-go-go-Related Gene inhibition - 0.4553 45.53%
Micronuclear + 0.6633 66.33%
Hepatotoxicity - 0.6073 60.73%
skin sensitisation - 0.9373 93.73%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity - 0.5250 52.50%
Nephrotoxicity - 0.8377 83.77%
Acute Oral Toxicity (c) III 0.6624 66.24%
Estrogen receptor binding + 0.7543 75.43%
Androgen receptor binding + 0.6652 66.52%
Thyroid receptor binding - 0.5346 53.46%
Glucocorticoid receptor binding + 0.6936 69.36%
Aromatase binding + 0.5542 55.42%
PPAR gamma + 0.6194 61.94%
Honey bee toxicity - 0.7613 76.13%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6349 63.49%
Fish aquatic toxicity + 0.7079 70.79%

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 99.77% 91.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 96.18% 94.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.17% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.25% 89.00%
CHEMBL2581 P07339 Cathepsin D 94.77% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.63% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.30% 86.33%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 91.79% 99.15%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.01% 99.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.02% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.24% 94.45%
CHEMBL3401 O75469 Pregnane X receptor 86.07% 94.73%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 84.94% 96.21%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.96% 96.00%
CHEMBL220 P22303 Acetylcholinesterase 82.16% 94.45%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.15% 92.62%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 81.64% 86.92%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.08% 95.89%

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.
Philotheca rhomboidea

Cross-Links

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PubChem 100997936
LOTUS LTS0218218
wikiData Q105328138