(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol

Details

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Internal ID a39d1ea8-27f2-4ae3-ba35-be9c9b691524
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
IUPAC Name (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol
SMILES (Canonical) COC1=C(C=CC(=C1)OC2C(C(C(C(O2)CO)O)O)O)OC3C(C(C(C(O3)CO)O)O)O
SMILES (Isomeric) COC1=C(C=CC(=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChI InChI=1S/C19H28O13/c1-28-9-4-7(29-18-16(26)14(24)12(22)10(5-20)31-18)2-3-8(9)30-19-17(27)15(25)13(23)11(6-21)32-19/h2-4,10-27H,5-6H2,1H3/t10-,11-,12-,13-,14+,15+,16-,17-,18-,19-/m1/s1
InChI Key XYTIVPVWLLNVKO-SKYGPZSASA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C19H28O13
Molecular Weight 464.40 g/mol
Exact Mass 464.15299094 g/mol
Topological Polar Surface Area (TPSA) 208.00 Ų
XlogP -3.20
Atomic LogP (AlogP) -3.95
H-Bond Acceptor 13
H-Bond Donor 8
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]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 - 0.8844 88.44%
Caco-2 - 0.8742 87.42%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.5974 59.74%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9298 92.98%
OATP1B3 inhibitior + 0.9721 97.21%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.6709 67.09%
P-glycoprotein inhibitior - 0.7446 74.46%
P-glycoprotein substrate - 0.9306 93.06%
CYP3A4 substrate - 0.5264 52.64%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7928 79.28%
CYP3A4 inhibition - 0.9407 94.07%
CYP2C9 inhibition - 0.8946 89.46%
CYP2C19 inhibition - 0.8842 88.42%
CYP2D6 inhibition - 0.9251 92.51%
CYP1A2 inhibition - 0.9271 92.71%
CYP2C8 inhibition - 0.6670 66.70%
CYP inhibitory promiscuity - 0.7395 73.95%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6280 62.80%
Eye corrosion - 0.9903 99.03%
Eye irritation - 0.9178 91.78%
Skin irritation - 0.8437 84.37%
Skin corrosion - 0.9603 96.03%
Ames mutagenesis - 0.7700 77.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7754 77.54%
Micronuclear - 0.5941 59.41%
Hepatotoxicity - 0.8250 82.50%
skin sensitisation - 0.8785 87.85%
Respiratory toxicity - 0.8111 81.11%
Reproductive toxicity - 0.5333 53.33%
Mitochondrial toxicity - 0.8125 81.25%
Nephrotoxicity - 0.7358 73.58%
Acute Oral Toxicity (c) III 0.7399 73.99%
Estrogen receptor binding - 0.5490 54.90%
Androgen receptor binding - 0.7286 72.86%
Thyroid receptor binding - 0.5091 50.91%
Glucocorticoid receptor binding + 0.5674 56.74%
Aromatase binding + 0.5384 53.84%
PPAR gamma - 0.5378 53.78%
Honey bee toxicity - 0.9031 90.31%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6649 66.49%
Fish aquatic toxicity - 0.7099 70.99%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.25% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.76% 91.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.02% 94.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.79% 99.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.75% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.37% 86.33%
CHEMBL4208 P20618 Proteasome component C5 89.10% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.55% 95.89%
CHEMBL241 Q14432 Phosphodiesterase 3A 84.78% 92.94%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 83.94% 86.92%
CHEMBL3401 O75469 Pregnane X receptor 82.70% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.96% 97.09%
CHEMBL2581 P07339 Cathepsin D 80.63% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.45% 92.62%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.06% 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.
Fraxinus sieboldiana

Cross-Links

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PubChem 16681195
LOTUS LTS0226230
wikiData Q105344653