(2S,3R,4S,5R,6R)-2-[(3S,4R,5S,6S)-6-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-3,4-dihydro-2H-chromen-3-yl]oxy]-4,5-dihydroxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

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Internal ID f086db66-f152-4528-9f6f-2670f10ca216
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
IUPAC Name (2S,3R,4S,5R,6R)-2-[(3S,4R,5S,6S)-6-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-3,4-dihydro-2H-chromen-3-yl]oxy]-4,5-dihydroxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) COC1=C(C2=C(C=C1O)OC(C(C2)OC3C(C(C(CO3)OC4C(C(C(C(O4)CO)O)O)O)O)O)C5=CC(=C(C=C5)O)O)O
SMILES (Isomeric) COC1=C(C2=C(C=C1O)O[C@@H]([C@H](C2)O[C@H]3[C@H]([C@H]([C@H](CO3)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)O)C5=CC(=C(C=C5)O)O)O
InChI InChI=1S/C27H34O16/c1-38-25-13(31)6-14-10(18(25)32)5-15(24(40-14)9-2-3-11(29)12(30)4-9)41-26-22(36)20(34)17(8-39-26)43-27-23(37)21(35)19(33)16(7-28)42-27/h2-4,6,15-17,19-24,26-37H,5,7-8H2,1H3/t15-,16+,17-,19-,20-,21-,22-,23+,24+,26-,27-/m0/s1
InChI Key UATBGOUAROWWQR-OXKGSLHXSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H34O16
Molecular Weight 614.50 g/mol
Exact Mass 614.18468499 g/mol
Topological Polar Surface Area (TPSA) 258.00 Ų
XlogP -1.70
Atomic LogP (AlogP) -2.16
H-Bond Acceptor 16
H-Bond Donor 10
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4S,5R,6R)-2-[(3S,4R,5S,6S)-6-[[(2R,3S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-3,4-dihydro-2H-chromen-3-yl]oxy]-4,5-dihydroxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6412 64.12%
Caco-2 - 0.9054 90.54%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.5420 54.20%
OATP2B1 inhibitior - 0.8581 85.81%
OATP1B1 inhibitior + 0.8299 82.99%
OATP1B3 inhibitior + 0.9815 98.15%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.4913 49.13%
P-glycoprotein inhibitior - 0.6475 64.75%
P-glycoprotein substrate - 0.6896 68.96%
CYP3A4 substrate + 0.6531 65.31%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7608 76.08%
CYP3A4 inhibition - 0.9531 95.31%
CYP2C9 inhibition - 0.8805 88.05%
CYP2C19 inhibition - 0.8251 82.51%
CYP2D6 inhibition - 0.9300 93.00%
CYP1A2 inhibition - 0.9016 90.16%
CYP2C8 inhibition + 0.6171 61.71%
CYP inhibitory promiscuity - 0.6657 66.57%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6152 61.52%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9182 91.82%
Skin irritation - 0.8330 83.30%
Skin corrosion - 0.9587 95.87%
Ames mutagenesis + 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7839 78.39%
Micronuclear + 0.6359 63.59%
Hepatotoxicity - 0.8177 81.77%
skin sensitisation - 0.9290 92.90%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.6556 65.56%
Mitochondrial toxicity - 0.5375 53.75%
Nephrotoxicity - 0.9443 94.43%
Acute Oral Toxicity (c) III 0.6564 65.64%
Estrogen receptor binding + 0.7784 77.84%
Androgen receptor binding + 0.5199 51.99%
Thyroid receptor binding + 0.5666 56.66%
Glucocorticoid receptor binding - 0.5460 54.60%
Aromatase binding + 0.5721 57.21%
PPAR gamma + 0.6939 69.39%
Honey bee toxicity - 0.7354 73.54%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity - 0.4153 41.53%

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 99.89% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 99.62% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.90% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.93% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.03% 86.33%
CHEMBL2581 P07339 Cathepsin D 90.73% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.76% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.67% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.40% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.24% 94.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.80% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.36% 95.89%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 83.21% 95.83%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.06% 96.00%
CHEMBL4208 P20618 Proteasome component C5 82.57% 90.00%
CHEMBL215 P09917 Arachidonate 5-lipoxygenase 81.82% 92.68%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 81.71% 96.37%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.69% 95.56%

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.
Bombax ceiba

Cross-Links

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PubChem 163040205
LOTUS LTS0254707
wikiData Q105269064