3-Hydroxy-5-[2-[2,3-dihydro-2alpha-(4-hydroxyphenyl)-3beta-(3,5-dihydroxyphenyl)benzofuran-5-yl]ethenyl]phenyl beta-D-glucopyranoside

Details

• Internal ID: 1e0d7f96-754c-4b49-83a6-bebad98b670e
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[3-[(E)-2-[(2S,3S)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C2C(C3=C(O2)C=CC(=C3)C=CC4=CC(=CC(=C4)OC5C(C(C(C(O5)CO)O)O)O)O)C6=CC(=CC(=C6)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H](C3=C(O2)C=CC(=C3)/C=C/C4=CC(=CC(=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)C6=CC(=CC(=C6)O)O)O
• InChI: InChI=1S/C34H32O11/c35-16-28-30(40)31(41)32(42)34(45-28)43-25-10-18(9-22(37)15-25)2-1-17-3-8-27-26(11-17)29(20-12-23(38)14-24(39)13-20)33(44-27)19-4-6-21(36)7-5-19/h1-15,28-42H,16H2/b2-1+/t28-,29+,30-,31+,32-,33-,34-/m1/s1
• InChI Key: FICNVOULKMUCLH-REZQOROLSA-N
• Popularity: 0 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

• DTXSID101101969
• 3-[(1E)-2-[(2S,3S)-3-(3,5-Dihydroxyphenyl)-2,3-dihydro-2-(4-hydroxyphenyl)-5-benzofuranyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside
• 3-Hydroxy-5-[2-[2,3-dihydro-2alpha-(4-hydroxyphenyl)-3beta-(3,5-dihydroxyphenyl)benzofuran-5-yl]ethenyl]phenyl beta-D-glucopyranoside
• 328090-94-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6558	65.58%
Caco-2	-	0.9063	90.63%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6186	61.86%
OATP2B1 inhibitior	-	0.5654	56.54%
OATP1B1 inhibitior	+	0.8533	85.33%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6877	68.77%
P-glycoprotein inhibitior	+	0.6147	61.47%
P-glycoprotein substrate	-	0.8262	82.62%
CYP3A4 substrate	+	0.6192	61.92%
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	+	0.7720	77.20%
CYP inhibitory promiscuity	+	0.6217	62.17%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5484	54.84%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8688	86.88%
Skin irritation	-	0.7987	79.87%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8026	80.26%
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	+	0.5176	51.76%
Acute Oral Toxicity (c)	III	0.5167	51.67%
Estrogen receptor binding	+	0.6782	67.82%
Androgen receptor binding	+	0.6479	64.79%
Thyroid receptor binding	+	0.6000	60.00%
Glucocorticoid receptor binding	-	0.4766	47.66%
Aromatase binding	-	0.5221	52.21%
PPAR gamma	+	0.7157	71.57%
Honey bee toxicity	-	0.6618	66.18%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
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	99.52%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	93.91%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.24%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.42%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	91.64%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.24%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.77%	86.33%
CHEMBL3194	P02766	Transthyretin	89.69%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.51%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.83%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.58%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.19%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.34%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.98%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.06%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.19%	86.92%
CHEMBL242	Q92731	Estrogen receptor beta	82.06%	98.35%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.67%	95.89%

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
• Vaccinium oxycoccos
• Vitis vinifera
• Wikstroemia retusa
• Zanthoxylum tetraspermum

Cross-Links

• PubChem: 10555800
• NPASS: NPC180144
• LOTUS: LTS0021502
• wikiData: Q104995621