(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(2R,3R)-6-hydroxy-4-[(2S,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 40080398-abe9-436d-8b17-5bbae1dcd72b
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(2R,3R)-6-hydroxy-4-[(2S,3S)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=C6C(C(OC6=CC(=C5)O)C7=CC=C(C=C7)O)C8=CC(=CC(=C8)OC9C(C(C(C(O9)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C\C2=C3[C@@H]([C@H](OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=C6[C@H]([C@@H](OC6=CC(=C5)O)C7=CC=C(C=C7)O)C8=CC(=CC(=C8)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O
• InChI: InChI=1S/C48H42O14/c49-22-38-43(56)44(57)45(58)48(62-38)59-34-17-27(16-31(53)18-34)40-41-35(19-33(55)21-37(41)61-46(40)24-5-11-29(51)12-6-24)42-39-26(4-1-23-2-9-28(50)10-3-23)15-32(54)20-36(39)60-47(42)25-7-13-30(52)14-8-25/h1-21,38,40,42-58H,22H2/b4-1-/t38-,40-,42+,43-,44+,45-,46+,47-,48-/m1/s1
• InChI Key: SZKVNSODIJRAET-AFLNQHFFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₄₂O₁₄
• Molecular Weight: 842.80 g/mol
• Exact Mass: 842.25745601 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.80
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6558	65.58%
Caco-2	-	0.8974	89.74%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6186	61.86%
OATP2B1 inhibitior	-	0.7085	70.85%
OATP1B1 inhibitior	+	0.8272	82.72%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7906	79.06%
P-glycoprotein inhibitior	+	0.6664	66.64%
P-glycoprotein substrate	-	0.7172	71.72%
CYP3A4 substrate	+	0.6482	64.82%
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	+	0.7925	79.25%
CYP inhibitory promiscuity	+	0.6217	62.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5484	54.84%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8886	88.86%
Skin irritation	-	0.7987	79.87%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8605	86.05%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.7894	78.94%
skin sensitisation	-	0.8497	84.97%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6914	69.14%
Acute Oral Toxicity (c)	III	0.5167	51.67%
Estrogen receptor binding	+	0.7648	76.48%
Androgen receptor binding	+	0.7244	72.44%
Thyroid receptor binding	+	0.5892	58.92%
Glucocorticoid receptor binding	-	0.4810	48.10%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7369	73.69%
Honey bee toxicity	-	0.6618	66.18%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
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	99.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.71%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.93%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	92.64%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.12%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.05%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.87%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.47%	89.00%
CHEMBL3194	P02766	Transthyretin	90.37%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	90.33%	98.35%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.01%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	89.06%	95.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.34%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.15%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.75%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.05%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.51%	91.71%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.48%	89.67%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.85%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.36%	94.45%

Plants that contains it

• Foeniculum vulgare

Cross-Links

• PubChem: 9988103
• LOTUS: LTS0212143
• wikiData: Q105264211