(2S,3R,4R,5R,6R)-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-[(E)-2-(4-hydroxyphenyl)ethenyl]-5-methoxyphenoxy]oxan-2-yl]methoxy]oxane-3,4,5-triol

Details

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Internal ID dfe4a54c-55df-4f5b-8973-5218062026b1
Taxonomy Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
IUPAC Name (2S,3R,4R,5R,6R)-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-[(E)-2-(4-hydroxyphenyl)ethenyl]-5-methoxyphenoxy]oxan-2-yl]methoxy]oxane-3,4,5-triol
SMILES (Canonical) CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=CC(=C3)OC)C=CC4=CC=C(C=C4)O)O)O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=CC(=C3)OC)/C=C/C4=CC=C(C=C4)O)O)O)O)O)O)O
InChI InChI=1S/C27H34O12/c1-13-20(29)22(31)24(33)26(37-13)36-12-19-21(30)23(32)25(34)27(39-19)38-18-10-15(9-17(11-18)35-2)4-3-14-5-7-16(28)8-6-14/h3-11,13,19-34H,12H2,1-2H3/b4-3+/t13-,19+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
InChI Key XKRQDCRMDCIEEB-MQKVEOCDSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C27H34O12
Molecular Weight 550.60 g/mol
Exact Mass 550.20502652 g/mol
Topological Polar Surface Area (TPSA) 188.00 Ų
XlogP 0.00
Atomic LogP (AlogP) -0.40
H-Bond Acceptor 12
H-Bond Donor 7
Rotatable Bonds 8

Synonyms

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BDBM50259882
trans-4'',5-dihydroxy-3-methoxystilbene-5-O-[alpha-L-rhamnopyranosyl-(1->6)]-beta-D-glucopyranoside

2D Structure

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2D Structure of (2S,3R,4R,5R,6R)-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-[(E)-2-(4-hydroxyphenyl)ethenyl]-5-methoxyphenoxy]oxan-2-yl]methoxy]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 - 0.7899 78.99%
Caco-2 - 0.8868 88.68%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.6394 63.94%
OATP2B1 inhibitior - 0.8558 85.58%
OATP1B1 inhibitior + 0.8965 89.65%
OATP1B3 inhibitior + 0.9592 95.92%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior - 0.4883 48.83%
P-glycoprotein inhibitior - 0.6811 68.11%
P-glycoprotein substrate - 0.7114 71.14%
CYP3A4 substrate + 0.5537 55.37%
CYP2C9 substrate - 0.6287 62.87%
CYP2D6 substrate - 0.8098 80.98%
CYP3A4 inhibition - 0.8476 84.76%
CYP2C9 inhibition - 0.9029 90.29%
CYP2C19 inhibition - 0.8494 84.94%
CYP2D6 inhibition - 0.8648 86.48%
CYP1A2 inhibition - 0.9236 92.36%
CYP2C8 inhibition + 0.6462 64.62%
CYP inhibitory promiscuity - 0.6141 61.41%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6015 60.15%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9386 93.86%
Skin irritation - 0.8475 84.75%
Skin corrosion - 0.9576 95.76%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3981 39.81%
Micronuclear + 0.5992 59.92%
Hepatotoxicity - 0.8373 83.73%
skin sensitisation - 0.8634 86.34%
Respiratory toxicity - 0.8111 81.11%
Reproductive toxicity + 0.5778 57.78%
Mitochondrial toxicity - 0.8000 80.00%
Nephrotoxicity - 0.8647 86.47%
Acute Oral Toxicity (c) III 0.7768 77.68%
Estrogen receptor binding + 0.6855 68.55%
Androgen receptor binding - 0.5928 59.28%
Thyroid receptor binding + 0.5878 58.78%
Glucocorticoid receptor binding - 0.5000 50.00%
Aromatase binding + 0.6229 62.29%
PPAR gamma + 0.6922 69.22%
Honey bee toxicity - 0.8168 81.68%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.8226 82.26%

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 99.17% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 96.15% 95.93%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 95.33% 96.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.02% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.54% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 92.83% 94.73%
CHEMBL3714130 P46095 G-protein coupled receptor 6 92.09% 97.36%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 90.89% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.11% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.82% 89.00%
CHEMBL2581 P07339 Cathepsin D 86.06% 98.95%
CHEMBL3194 P02766 Transthyretin 85.94% 90.71%
CHEMBL242 Q92731 Estrogen receptor beta 85.75% 98.35%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 84.72% 91.71%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.47% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.44% 99.17%
CHEMBL4208 P20618 Proteasome component C5 82.85% 90.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 81.76% 89.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.00% 97.09%

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.
Boswellia papyrifera
Elephantorrhiza goetzei

Cross-Links

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PubChem 11168830
NPASS NPC3293
LOTUS LTS0214539
wikiData Q104888826