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

Details

• Internal ID: 7fd67591-7091-45b7-8b5f-193e7c90dfa1
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[3-(3,5-dihydroxyphenyl)-6-[(E)-2-(4-hydroxyphenyl)ethenyl]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-benzofuran-2-yl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=CC3=C(C(=C2)OC4C(C(C(C(O4)CO)O)O)O)C(=C(O3)C5=CC=C(C=C5)OC6C(C(C(C(O6)CO)O)O)O)C7=CC(=CC(=C7)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=CC3=C(C(=C2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C(=C(O3)C5=CC=C(C=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C7=CC(=CC(=C7)O)O)O
• InChI: InChI=1S/C40H40O16/c41-16-28-32(46)34(48)36(50)39(55-28)52-25-9-5-20(6-10-25)38-30(21-13-23(44)15-24(45)14-21)31-26(53-38)11-19(2-1-18-3-7-22(43)8-4-18)12-27(31)54-40-37(51)35(49)33(47)29(17-42)56-40/h1-15,28-29,32-37,39-51H,16-17H2/b2-1+/t28-,29-,32-,33-,34+,35+,36-,37-,39-,40-/m1/s1
• InChI Key: VKWMXDFMNSNJER-HEZIKDLRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₀O₁₆
• Molecular Weight: 776.70 g/mol
• Exact Mass: 776.23163518 g/mol
• Topological Polar Surface Area (TPSA): 273.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.41
• H-Bond Acceptor: 16
• H-Bond Donor: 11
• 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	-	0.9000	90.00%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6106	61.06%
OATP2B1 inhibitior	-	0.5684	56.84%
OATP1B1 inhibitior	+	0.9144	91.44%
OATP1B3 inhibitior	+	0.9649	96.49%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8306	83.06%
P-glycoprotein inhibitior	+	0.6789	67.89%
P-glycoprotein substrate	-	0.7060	70.60%
CYP3A4 substrate	+	0.6412	64.12%
CYP2C9 substrate	+	0.5537	55.37%
CYP2D6 substrate	-	0.8194	81.94%
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	+	0.8845	88.45%
CYP inhibitory promiscuity	+	0.6287	62.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5320	53.20%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.8928	89.28%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8454	84.54%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.7697	76.97%
skin sensitisation	-	0.8530	85.30%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7816	78.16%
Acute Oral Toxicity (c)	III	0.5369	53.69%
Estrogen receptor binding	+	0.8141	81.41%
Androgen receptor binding	+	0.7031	70.31%
Thyroid receptor binding	+	0.5607	56.07%
Glucocorticoid receptor binding	-	0.5092	50.92%
Aromatase binding	+	0.5712	57.12%
PPAR gamma	+	0.7565	75.65%
Honey bee toxicity	-	0.6802	68.02%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
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	99.21%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	97.19%	98.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.69%	89.00%
CHEMBL3194	P02766	Transthyretin	96.01%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.76%	96.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	93.77%	91.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.40%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	92.98%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.97%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.59%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.21%	94.73%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	89.64%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.46%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.37%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.24%	94.00%
CHEMBL2581	P07339	Cathepsin D	87.87%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.36%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.20%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.14%	95.56%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.78%	97.53%
CHEMBL226	P30542	Adenosine A1 receptor	85.22%	95.93%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.89%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.81%	96.09%

Plants that contains it

• Anigozanthos preissii
• Millettia erythrocalyx

Cross-Links

• PubChem: 162906048
• LOTUS: LTS0272283
• wikiData: Q104908804