(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

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Internal ID 91e568e3-fbfd-4fc4-b3f9-abbac45f5bc7
Taxonomy Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
IUPAC Name (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) C1=CC(=CC=C1C=CC2=CC(=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O
SMILES (Isomeric) C1=CC(=CC=C1C=CC2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
InChI InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/t16-,17-,18+,19-,20-/m1/s1
InChI Key HSTZMXCBWJGKHG-OUUBHVDSSA-N
Popularity 195 references in papers

Physical and Chemical Properties

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Molecular Formula C20H22O8
Molecular Weight 390.40 g/mol
Exact Mass 390.13146766 g/mol
Topological Polar Surface Area (TPSA) 140.00 Ų
XlogP 1.70
Atomic LogP (AlogP) 0.45
H-Bond Acceptor 8
H-Bond Donor 6
Rotatable Bonds 5

Synonyms

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(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
resveratrol-3-O-beta-d-glucopyranoside
PD057190
Q27166434
3-Hydroxy-5-(2-(4-hydroxyphenyl)ethenyl)phenyl-beta-D-glucopyranoside

2D Structure

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2D Structure of (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy]-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 - 0.7754 77.54%
Caco-2 - 0.9112 91.12%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.6082 60.82%
OATP2B1 inhibitior - 0.5646 56.46%
OATP1B1 inhibitior + 0.9321 93.21%
OATP1B3 inhibitior + 0.9608 96.08%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior - 0.7386 73.86%
P-glycoprotein inhibitior - 0.8421 84.21%
P-glycoprotein substrate - 0.9564 95.64%
CYP3A4 substrate - 0.5106 51.06%
CYP2C9 substrate + 0.5811 58.11%
CYP2D6 substrate - 0.8191 81.91%
CYP3A4 inhibition - 0.8716 87.16%
CYP2C9 inhibition - 0.8927 89.27%
CYP2C19 inhibition - 0.8555 85.55%
CYP2D6 inhibition - 0.9183 91.83%
CYP1A2 inhibition - 0.9329 93.29%
CYP2C8 inhibition + 0.5543 55.43%
CYP inhibitory promiscuity - 0.5977 59.77%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6352 63.52%
Eye corrosion - 0.9939 99.39%
Eye irritation - 0.8273 82.73%
Skin irritation - 0.8444 84.44%
Skin corrosion - 0.9676 96.76%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5167 51.67%
Micronuclear - 0.5141 51.41%
Hepatotoxicity - 0.9498 94.98%
skin sensitisation - 0.8099 80.99%
Respiratory toxicity - 0.7667 76.67%
Reproductive toxicity + 0.5556 55.56%
Mitochondrial toxicity - 0.7625 76.25%
Nephrotoxicity - 0.6328 63.28%
Acute Oral Toxicity (c) III 0.6904 69.04%
Estrogen receptor binding + 0.5728 57.28%
Androgen receptor binding + 0.5778 57.78%
Thyroid receptor binding + 0.6521 65.21%
Glucocorticoid receptor binding - 0.5505 55.05%
Aromatase binding + 0.7383 73.83%
PPAR gamma + 0.7857 78.57%
Honey bee toxicity - 0.7190 71.90%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.8347 83.47%

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 99.04% 91.11%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 92.84% 96.00%
CHEMBL226 P30542 Adenosine A1 receptor 92.79% 95.93%
CHEMBL3194 P02766 Transthyretin 92.41% 90.71%
CHEMBL3401 O75469 Pregnane X receptor 92.04% 94.73%
CHEMBL242 Q92731 Estrogen receptor beta 89.95% 98.35%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.29% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.07% 86.33%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 87.54% 86.92%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.78% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.76% 95.56%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 85.48% 91.71%
CHEMBL2581 P07339 Cathepsin D 85.39% 98.95%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.11% 95.89%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.90% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.88% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.68% 95.89%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 82.36% 89.67%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 80.52% 85.00%

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.
Acacia adunca
Aconitum seravschanicum
Adansonia grandidieri
Adiantum philippense
Aldama incana
Alkekengi officinarum
Annona cornifolia
Aphyllocladus denticulatus
Aristeguietia glutinosa
Artemisia pedemontana subsp. assoana
Astragalus sempervirens
Bassia muricata
Calostephane divaricata
Caragana aurantiaca
Chaenomeles sinensis
Cinnamosma macrocarpa
Dendriopoterium menendezii
Dianthera secunda
Dodonaea viscosa
Dumortiera hirsuta
Dysoxylum cumingianum
Echeveria secunda
Enceliopsis argophylla
Eucalyptus melliodora
Flacourtia jangomas
Galatella sedifolia subsp. sedifolia
Gnetum latifolium
Goniothalamus malayanus
Hedysarum inundatum
Hypericum laricifolium
Ipomoea digitata
Lavandula angustifolia subsp. pyrenaica
Lepisorus ussuriensis
Leptinella filicula
Leucosceptrum canum
Lysimachia mauritiana
Marrubium anisodon
Maytenus imbricata
Miliusa velutina
Naucleopsis ternstroemiiflora
Neobalanocarpus heimii
Ocotea pittieri
Onobrychis arenaria
Packera toluccana
Pastinaca sativa
Peltostigma guatemalense
Piper caninum
Polyalthia evecta
Premna odorata
Psychotria stachyoides
Rauvolfia vomitoria
Reynoutria japonica
Rhodanthe chlorocephala subsp. rosea
Rumex maritimus
Salvia syriaca
Scutellaria amoena
Senecio subdentatus
Sideritis chamaedryfolia
Solanum laxum
Swertia franchetiana
Teucrium yemense
Trichotosia mollis
Vaccinium oxycoccos
Vatica rassak
Vitis vinifera
Wikstroemia retusa
Zanthoxylum tetraspermum

Cross-Links

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PubChem 73642
NPASS NPC142153