(3R,4S,5S,6R)-2-[3-hydroxy-5-[(2S,3S)-8-hydroxy-2-(4-hydroxyphenyl)-10-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydronaphtho[2,1-e][1]benzofuran-3-yl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: f76dc460-013c-4084-8cfb-01b6f869faa4
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (3R,4S,5S,6R)-2-[3-hydroxy-5-[(2S,3S)-8-hydroxy-2-(4-hydroxyphenyl)-10-[(3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydronaphtho[2,1-e][1]benzofuran-3-yl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC2=C1C=CC3=C4C(C(OC4=CC(=C32)OC5C(C(C(C(O5)CO)O)O)O)C6=CC=C(C=C6)O)C7=CC(=CC(=C7)OC8C(C(C(C(O8)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC2=C1C=CC3=C4[C@@H]([C@H](OC4=CC(=C32)OC5[C@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O)C6=CC=C(C=C6)O)C7=CC(=CC(=C7)OC8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O
• InChI: InChI=1S/C40H40O16/c41-14-27-32(46)34(48)36(50)39(55-27)52-22-10-18(9-21(45)11-22)29-31-23-8-4-16-1-7-20(44)12-24(16)30(23)25(54-40-37(51)35(49)33(47)28(15-42)56-40)13-26(31)53-38(29)17-2-5-19(43)6-3-17/h1-13,27-29,32-51H,14-15H2/t27-,28+,29+,32-,33+,34+,35-,36-,37+,38-,39?,40?/m1/s1
• InChI Key: RXVROCWTMVACDR-SOUOMJQJSA-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): 269.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 0.73
• H-Bond Acceptor: 16
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5322	53.22%
Caco-2	-	0.9078	90.78%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6355	63.55%
OATP2B1 inhibitior	-	0.8471	84.71%
OATP1B1 inhibitior	+	0.8322	83.22%
OATP1B3 inhibitior	+	0.9551	95.51%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8309	83.09%
P-glycoprotein inhibitior	+	0.6239	62.39%
P-glycoprotein substrate	-	0.6096	60.96%
CYP3A4 substrate	+	0.6446	64.46%
CYP2C9 substrate	-	0.8050	80.50%
CYP2D6 substrate	-	0.7781	77.81%
CYP3A4 inhibition	-	0.8947	89.47%
CYP2C9 inhibition	-	0.8581	85.81%
CYP2C19 inhibition	-	0.7341	73.41%
CYP2D6 inhibition	-	0.8633	86.33%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	+	0.7712	77.12%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5436	54.36%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.8908	89.08%
Skin irritation	-	0.8220	82.20%
Skin corrosion	-	0.9604	96.04%
Ames mutagenesis	+	0.6363	63.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.8759	87.59%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8941	89.41%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.6768	67.68%
Acute Oral Toxicity (c)	III	0.5444	54.44%
Estrogen receptor binding	+	0.8151	81.51%
Androgen receptor binding	+	0.6157	61.57%
Thyroid receptor binding	+	0.6002	60.02%
Glucocorticoid receptor binding	-	0.6700	67.00%
Aromatase binding	+	0.5687	56.87%
PPAR gamma	+	0.7911	79.11%
Honey bee toxicity	-	0.6900	69.00%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5349	53.49%
Fish aquatic toxicity	+	0.7930	79.30%

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	99.54%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.10%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.69%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.64%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.54%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.29%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.64%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.47%	89.62%
CHEMBL3401	O75469	Pregnane X receptor	87.32%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.59%	95.78%
CHEMBL242	Q92731	Estrogen receptor beta	85.56%	98.35%
CHEMBL2581	P07339	Cathepsin D	84.99%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.41%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	83.89%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.75%	94.45%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	82.91%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.56%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.86%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.39%	99.15%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.47%	95.83%

Plants that contains it

• Iris tingitana

Cross-Links

• PubChem: 163070407
• LOTUS: LTS0157626
• wikiData: Q105247315