(2S,3R,4S,5S,6R)-2-[4-[(E)-2-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-[2-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 91ea8734-e3eb-482f-9cd5-71b80b408fef
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(E)-2-[(2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-[2-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2,3-dihydro-1-benzofuran-4-yl]ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)O)C4=C(C=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)O)C6=CC(=CC(=C6)O)O)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=C3[C@@H]([C@H](OC3=CC(=C2)O)C4=C(C=C(C=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[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C40H42O17/c41-15-28-32(47)34(49)36(51)39(56-28)53-23-5-2-17(3-6-23)1-4-18-9-22(45)13-27-30(18)31(19-10-20(43)12-21(44)11-19)38(55-27)25-8-7-24(14-26(25)46)54-40-37(52)35(50)33(48)29(16-42)57-40/h1-14,28-29,31-52H,15-16H2/b4-1+/t28-,29-,31+,32-,33-,34+,35+,36-,37-,38-,39-,40-/m1/s1
• InChI Key: OWLXXVWIIHKHMS-DLSZBKKWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₂O₁₇
• Molecular Weight: 794.70 g/mol
• Exact Mass: 794.24219987 g/mol
• Topological Polar Surface Area (TPSA): 289.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 17
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5892	58.92%
Caco-2	-	0.8870	88.70%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6106	61.06%
OATP2B1 inhibitior	-	0.7098	70.98%
OATP1B1 inhibitior	+	0.8801	88.01%
OATP1B3 inhibitior	+	0.9649	96.49%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8059	80.59%
P-glycoprotein inhibitior	+	0.6626	66.26%
P-glycoprotein substrate	-	0.7382	73.82%
CYP3A4 substrate	+	0.6458	64.58%
CYP2C9 substrate	-	0.8137	81.37%
CYP2D6 substrate	-	0.8014	80.14%
CYP3A4 inhibition	-	0.8884	88.84%
CYP2C9 inhibition	-	0.8675	86.75%
CYP2C19 inhibition	-	0.7045	70.45%
CYP2D6 inhibition	-	0.8053	80.53%
CYP1A2 inhibition	-	0.8621	86.21%
CYP2C8 inhibition	+	0.7341	73.41%
CYP inhibitory promiscuity	+	0.6287	62.87%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5320	53.20%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.8935	89.35%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	-	0.5037	50.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.8379	83.79%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.7925	79.25%
skin sensitisation	-	0.8530	85.30%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7071	70.71%
Acute Oral Toxicity (c)	III	0.5369	53.69%
Estrogen receptor binding	+	0.7204	72.04%
Androgen receptor binding	+	0.6166	61.66%
Thyroid receptor binding	+	0.5772	57.72%
Glucocorticoid receptor binding	-	0.5452	54.52%
Aromatase binding	+	0.5292	52.92%
PPAR gamma	+	0.7200	72.00%
Honey bee toxicity	-	0.7501	75.01%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9041	90.41%

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	99.39%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.65%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.61%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.16%	95.93%
CHEMBL3194	P02766	Transthyretin	93.67%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.61%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.93%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.98%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.87%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.72%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.05%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.23%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.75%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	87.40%	91.49%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.38%	91.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.69%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.61%	95.78%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.64%	89.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.29%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.96%	97.36%
CHEMBL4208	P20618	Proteasome component C5	81.60%	90.00%

Plants that contains it

• Gnetum africanum

Cross-Links

• PubChem: 101197168
• LOTUS: LTS0105051
• wikiData: Q104667148