(2R,3S)-8-[(2R,3S,4S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-chromen-4-yl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

Details

• Internal ID: e9aee9e7-da2d-44ea-b4cd-913bcdac6cc3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (2R,3S)-8-[(2R,3S,4S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-chromen-4-yl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC=C(C=C5)O)OC6C(C(C(C(O6)CO)O)O)O)O)O)C7=CC(=C(C=C7)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@H]3[C@@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC=C(C=C5)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)C7=CC(=C(C=C7)O)O)O
• InChI: InChI=1S/C36H36O16/c37-12-25-29(46)30(47)31(48)36(50-25)52-35-28(26-21(43)8-16(39)9-24(26)49-33(35)13-1-4-15(38)5-2-13)27-22(44)11-19(41)17-10-23(45)32(51-34(17)27)14-3-6-18(40)20(42)7-14/h1-9,11,23,25,28-33,35-48H,10,12H2/t23-,25+,28-,29+,30-,31+,32+,33+,35-,36-/m0/s1
• InChI Key: RXAUKFAEOYCJSH-LHGZWCACSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₆O₁₆
• Molecular Weight: 724.70 g/mol
• Exact Mass: 724.20033506 g/mol
• Topological Polar Surface Area (TPSA): 280.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.11
• H-Bond Acceptor: 16
• H-Bond Donor: 12
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5547	55.47%
Caco-2	-	0.9114	91.14%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.4774	47.74%
OATP2B1 inhibitior	-	0.8450	84.50%
OATP1B1 inhibitior	+	0.8212	82.12%
OATP1B3 inhibitior	+	0.9229	92.29%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8556	85.56%
P-glycoprotein inhibitior	+	0.6311	63.11%
P-glycoprotein substrate	-	0.6382	63.82%
CYP3A4 substrate	+	0.6653	66.53%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.7645	76.45%
CYP3A4 inhibition	-	0.9445	94.45%
CYP2C9 inhibition	-	0.9517	95.17%
CYP2C19 inhibition	-	0.9182	91.82%
CYP2D6 inhibition	-	0.9153	91.53%
CYP1A2 inhibition	-	0.9314	93.14%
CYP2C8 inhibition	+	0.7518	75.18%
CYP inhibitory promiscuity	-	0.8598	85.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6637	66.37%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.8891	88.91%
Skin irritation	-	0.8035	80.35%
Skin corrosion	-	0.9654	96.54%
Ames mutagenesis	+	0.5663	56.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.9088	90.88%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.9177	91.77%
skin sensitisation	-	0.9033	90.33%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6682	66.82%
Acute Oral Toxicity (c)	III	0.4873	48.73%
Estrogen receptor binding	+	0.7950	79.50%
Androgen receptor binding	+	0.6935	69.35%
Thyroid receptor binding	+	0.6033	60.33%
Glucocorticoid receptor binding	-	0.5796	57.96%
Aromatase binding	+	0.5367	53.67%
PPAR gamma	+	0.7369	73.69%
Honey bee toxicity	-	0.6717	67.17%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.6895	68.95%

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	99.79%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.83%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.45%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	93.62%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	90.63%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.18%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.90%	95.93%
CHEMBL4208	P20618	Proteasome component C5	88.52%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.20%	99.15%
CHEMBL233	P35372	Mu opioid receptor	87.64%	97.93%
CHEMBL2581	P07339	Cathepsin D	86.85%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.81%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.58%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.38%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.26%	86.33%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.47%	97.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.02%	95.89%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.50%	96.37%
CHEMBL3194	P02766	Transthyretin	80.98%	90.71%
CHEMBL236	P41143	Delta opioid receptor	80.21%	99.35%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.18%	97.36%

Plants that contains it

• Quercus ilex

Cross-Links

• PubChem: 102286039
• LOTUS: LTS0240554
• wikiData: Q105246884