(2s,3s)-3-(3,5-Dihydroxyphenyl)-2-(4-Hydroxyphenyl)-4-[(E)-2-(4-Hydroxyphenyl)ethenyl]-2,3-Dihydro-1-Benzofuran-6-Yl Beta-D-Glucopyranoside

Details

• Internal ID: bb39f2a7-6d72-42e6-87ce-69c7f43791a2
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(2S,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)OC4C(C(C(C(O4)CO)O)O)O)C5=CC=C(C=C5)O)C6=CC(=CC(=C6)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=C3[C@@H]([C@H](OC3=CC(=C2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=CC=C(C=C5)O)C6=CC(=CC(=C6)O)O)O
• InChI: InChI=1S/C34H32O11/c35-16-27-30(40)31(41)32(42)34(45-27)43-25-13-19(4-1-17-2-7-21(36)8-3-17)28-26(15-25)44-33(18-5-9-22(37)10-6-18)29(28)20-11-23(38)14-24(39)12-20/h1-15,27,29-42H,16H2/b4-1+/t27-,29+,30-,31+,32-,33-,34-/m1/s1
• InChI Key: NHYFNLFVNSLRES-YNVKLIFMSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₃₂O₁₁
• Molecular Weight: 616.60 g/mol
• Exact Mass: 616.19446183 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.12
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• 23Y
• Epsilon-Viniferin Glucoside
• CHEMBL1082598
• Q27452689
• ;(2S,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-6-yl
• 2alpha-(4-Hydroxyphenyl)-3beta-(3,5-dihydroxyphenyl)-4-[(E)-4-hydroxystyryl]-6-(beta-D-glucopyranosyloxy)-2,3-dihydrobenzofuran

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6558	65.58%
Caco-2	-	0.9212	92.12%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6186	61.86%
OATP2B1 inhibitior	-	0.5679	56.79%
OATP1B1 inhibitior	+	0.8343	83.43%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8396	83.96%
P-glycoprotein inhibitior	+	0.6535	65.35%
P-glycoprotein substrate	-	0.7902	79.02%
CYP3A4 substrate	+	0.6179	61.79%
CYP2C9 substrate	-	0.8137	81.37%
CYP2D6 substrate	-	0.8014	80.14%
CYP3A4 inhibition	-	0.8599	85.99%
CYP2C9 inhibition	-	0.8470	84.70%
CYP2C19 inhibition	-	0.7403	74.03%
CYP2D6 inhibition	-	0.8204	82.04%
CYP1A2 inhibition	-	0.8388	83.88%
CYP2C8 inhibition	+	0.7575	75.75%
CYP inhibitory promiscuity	+	0.6217	62.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5484	54.84%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8502	85.02%
Skin irritation	-	0.7987	79.87%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.5537	55.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8206	82.06%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.8550	85.50%
skin sensitisation	-	0.8497	84.97%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5654	56.54%
Acute Oral Toxicity (c)	III	0.5167	51.67%
Estrogen receptor binding	+	0.7241	72.41%
Androgen receptor binding	+	0.7057	70.57%
Thyroid receptor binding	+	0.6681	66.81%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.4826	48.26%
PPAR gamma	+	0.7764	77.64%
Honey bee toxicity	-	0.7161	71.61%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9174	91.74%

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%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.80%	96.00%
CHEMBL3194	P02766	Transthyretin	94.12%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.42%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.78%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.36%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.19%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.68%	86.33%
CHEMBL242	Q92731	Estrogen receptor beta	85.89%	98.35%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.81%	86.92%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.05%	89.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.64%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.42%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.80%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.59%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.43%	95.78%
CHEMBL2581	P07339	Cathepsin D	82.20%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.36%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.35%	91.71%
CHEMBL226	P30542	Adenosine A1 receptor	81.25%	95.93%
CHEMBL4208	P20618	Proteasome component C5	81.04%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.07%	99.15%

Plants that contains it

• Acacia adunca
• Adiantum philippense
• Aldama incana
• Annona cornifolia
• Artemisia pedemontana subsp. assoana
• Astragalus sempervirens
• Calostephane divaricata
• Caragana aurantiaca
• Chaenomeles sinensis
• Dumortiera hirsuta
• Echeveria secunda
• Eucalyptus melliodora
• Gnetum latifolium
• Goniothalamus malayanus
• Hedysarum inundatum
• Hypericum laricifolium
• Ipomoea digitata
• Lepisorus ussuriensis
• Lysimachia mauritiana
• Marrubium anisodon
• Naucleopsis ternstroemiiflora
• Ocotea pittieri
• Pastinaca sativa
• Peltostigma guatemalense
• Premna odorata
• Rauvolfia vomitoria
• Rhodanthe chlorocephala subsp. rosea
• Rumex maritimus
• Salvia syriaca
• Scutellaria amoena
• Solanum laxum
• Swertia franchetiana
• Upuna borneensis
• Vaccinium oxycoccos
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 46890010
• NPASS: NPC233467
• ChEMBL: CHEMBL1082598
• LOTUS: LTS0153391
• wikiData: Q27452689