2,3,5,4''-Tetrahydroxystilbene-2-O-beta-D-glucoside

Details

• Internal ID: f32d4bb1-67f5-4faa-8691-eb8f4c6ae28d
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• InChI: InChI=1S/C20H22O9/c21-9-15-16(25)17(26)18(27)20(28-15)29-19-11(7-13(23)8-14(19)24)4-1-10-2-5-12(22)6-3-10/h1-8,15-18,20-27H,9H2/b4-1+/t15-,16-,17+,18-,20+/m1/s1
• InChI Key: JAYVHSBYKLLDJC-DSNJPTTOSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₉
• Molecular Weight: 406.40 g/mol
• Exact Mass: 406.12638228 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• 54QRI6OKJ5
• 2,3,4',5-Tetrahydroxystilbene 2-o-D-glucoside
• 2,3,5,4'-Tetrahydroxystilbene-2-O-beta-D-glucoside
• DTXSID801242061
• (E)-2,3,5,4'-Tetrahydroxy stilbene-2-O-glucoside
• 2,4-Dihydroxy-6-((1E)-2-(4-hydroxyphenyl)ethenyl)phenyl beta-D-glucopyranoside
• beta-D-Glucopyranoside, 2,4-dihydroxy-6-((1E)-2-(4-hydroxyphenyl)ethenyl)phenyl
• beta-D-Glucopyranoside, 2,4-dihydroxy-6-(2-(4-hydroxyphenyl)ethenyl)phenyl, (E)-
• 2,3,5,4'-tetrahydroxystilbene 2-O-beta-D-glucoside
• RefChem:25885
• DTXCID601672945
• 2-(2,4-dihydroxy-6-(2-(4-hydroxyphenyl)ethenyl)phenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• 2,3,4',5-tetrahydroxystilbene-2-O-beta-D-glucoside
• 2,3,5,4'-tetrahydroxystilbene-2-O-D-glucoside
• 2,3,5,4'-Tetrahydroxystilbene 2-O-glucoside
• 55327-45-2
• 2,3,5,4-tetrahydroxyl diphenylethylene-2-o-glucoside
• 2,3,5,4'-Tetrahydroxystilbene-2-O-b-D-glucopyranoside
• (2S,3R,4S,5S,6R)-2-(2,4-dihydroxy-6-((E)-4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• EH-201
• MFCD00238694
• CHEMBL460860
• 2,3,5,4'-Tetrahydroxyl diphenylethylene-2-O-glucoside
• 2,3,4',5-Tetrahydroxystilbene 2-O-Glucoside
• 2,3,4',5-Tetrahydroxystilbene 2-O-|A-D-glucoside
• 2,3,5,4'-Tetrahydroxyl-diphenylethylene-2-O-beta-D-glucoside
• 2,3,5,4'-tetrahydroxystilbene-2-o-beta-d-glucopyranoside
• (2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
• tetrahydroxyl diphenylethylene-2-o-glucoside
• 2,3,5,4'-Tetrahydroxy stilbene-2-O-beta-D-glucoside
• THSG
• tetrahydroxyldiphenylethylene-2-o-glucoside
• UNII-54QRI6OKJ5
• tetrahydroxystilbene glucoside
• orb1304795
• SCHEMBL17507729
• HY-N0652R
• CHEBI:140850
• GLXC-02856
• HY-N0403
• BDBM50020713
• s3906
• AKOS030530177
• AKOS040758637
• beta-D-Glucopyranoside, 2,4-dihydroxy-6-(2-(4-hydroxyphenyl)ethenyl)phenyl
• CCG-268716
• MT08982
• NCGC00482790-01
• Tetrahydroxystilbene-2-O-??-D-glucoside
• 4CN-2816
• AC-33974
• AS-76404
• DA-69632
• Tetrahydroxystilbene-2-O-beta-D-glucoside
• TS-09048
• CS-0008935
• T3513
• F16062
• 2,3,5,4'-Tetrahydroxy stilbene-2---D-glucoside
• 2,3,5,4'-Tetrahydroxystilbene 2-O--D-glucoside
• 373T942
• 2,3,5,4'-Tetrahydroxystilbene 2-O-fA-D-Glucoside
• 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside
• 2,3,5,4'-Tetrahydroxystilbene-2-O-|A-D-glucoside
• 2,3,5,4'-Tetrahydroxystilbene-2-O-ss-D-glucoside
• 2,3,5,4-tetrahydroxyl-diphenylethylene-2-o-glucoside
• (E)-2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside
• 2,3,5,4-Tetrahydroxy stilbene-2-Omicron-beta-D-glucoside
• 2,3,5,4-Tetrahydroxystilbene-2-O-beta-D-glucopyranoside
• 2,3,5,4a(2)-Tetrahydroxystilbene 2-O-I(2)-D-glucoside
• trans-2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside
• 2,3,5,4'-Tetrahydroxystilbene 2-O-|A-D-glucoside (Standard)
• 2,3,5,4'-TETRAHYDROXYSTILBENE-2-O-.BETA.-D-GLUCOSIDE
• 2,3,5,4'-TETRAHYDROXYSTILBENE-2-O-BETA-D-GLUCOSIDE [USP-RS]
• .BETA.-D-GLUCOPYRANOSIDE, 2,4-DIHYDROXY-6-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)PHENYL
• .BETA.-D-GLUCOPYRANOSIDE, 2,4-DIHYDROXY-6-(2-(4-HYDROXYPHENYL)ETHENYL)PHENYL, (E)-
• 2,4-DIHYDROXY-6-((1E)-2-(4-HYDROXYPHENYL)ETHENYL)PHENYL .BETA.-D-GLUCOPYRANOSIDE
• 2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenyl beta-D-glucopyranoside
• b-D-Glucopyranoside,2,4-dihydroxy-6-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl
• B-D-GLUCOPYRANOSIDE,2,4-DIHYDROXY-6-[2-(4-HYDROXYPHENYL)ETHENYL]PHENYL
• 2,3,5,4'-Tetrahydroxystilbene 2-O-AfAE'A centa' notA inverted exclamation markAfasA'A|AfAE'Adaggeratrade markAfA centA centasA notA em leaderA inverted exclamation mark-D-glucoside
• TSG

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7283	72.83%
Caco-2	-	0.9137	91.37%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5553	55.53%
OATP2B1 inhibitior	+	0.5746	57.46%
OATP1B1 inhibitior	+	0.8712	87.12%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6298	62.98%
P-glycoprotein inhibitior	-	0.7297	72.97%
P-glycoprotein substrate	-	0.9247	92.47%
CYP3A4 substrate	+	0.5216	52.16%
CYP2C9 substrate	+	0.5811	58.11%
CYP2D6 substrate	-	0.8191	81.91%
CYP3A4 inhibition	-	0.8471	84.71%
CYP2C9 inhibition	-	0.8424	84.24%
CYP2C19 inhibition	-	0.8155	81.55%
CYP2D6 inhibition	-	0.9002	90.02%
CYP1A2 inhibition	-	0.9137	91.37%
CYP2C8 inhibition	+	0.6836	68.36%
CYP inhibitory promiscuity	-	0.5561	55.61%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6854	68.54%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.7416	74.16%
Skin irritation	-	0.8338	83.38%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3897	38.97%
Micronuclear	+	0.5359	53.59%
Hepatotoxicity	-	0.8675	86.75%
skin sensitisation	-	0.7594	75.94%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.7208	72.08%
Acute Oral Toxicity (c)	III	0.6964	69.64%
Estrogen receptor binding	-	0.4789	47.89%
Androgen receptor binding	+	0.6454	64.54%
Thyroid receptor binding	+	0.6397	63.97%
Glucocorticoid receptor binding	-	0.5433	54.33%
Aromatase binding	+	0.5573	55.73%
PPAR gamma	+	0.7488	74.88%
Honey bee toxicity	-	0.7750	77.50%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8707	87.07%

Targets

Proven Targets:

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	99.51%	91.11%
CHEMBL3194	P02766	Transthyretin	96.57%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.08%	96.00%
CHEMBL242	Q92731	Estrogen receptor beta	91.32%	98.35%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.80%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.56%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.96%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	88.85%	94.73%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	88.56%	89.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.99%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	86.99%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.86%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.70%	94.45%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	85.27%	88.00%
CHEMBL4208	P20618	Proteasome component C5	82.56%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.87%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.30%	99.15%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.39%	91.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.25%	95.64%
CHEMBL226	P30542	Adenosine A1 receptor	80.18%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.05%	95.56%

Plants that contains it

• Aconitum seravschanicum
• Adansonia grandidieri
• Alkekengi officinarum
• Aphyllocladus denticulatus
• Bassia muricata
• Dianthera secunda
• Dodonaea viscosa
• Enceliopsis argophylla
• Epicharis cumingiana
• Euphorbia smirnovii
• Flacourtia jangomas
• Galatella sedifolia subsp. sedifolia
• Hopea reticulata
• Lavandula angustifolia subsp. pyrenaica
• Miliusa velutina
• Neobalanocarpus heimii
• Onobrychis arenaria
• Psychotria stachyoides
• Reynoutria japonica
• Reynoutria multiflora
• Sanguisorba menendezii
• Senecio subdentatus
• Teucrium yemense
• Trichotosia mollis

Cross-Links

• PubChem: 5321884
• NPASS: NPC252169
• LOTUS: LTS0082519
• wikiData: Q76303607