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

Details

• Internal ID: f8eede49-6d01-4f07-813e-ad6dcba66c82
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(2S,3R)-6-hydroxy-2-(4-hydroxyphenyl)-4-[(2R,3R)-2-(4-hydroxyphenyl)-4-[(Z)-2-(4-hydroxyphenyl)ethenyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydro-1-benzofuran-3-yl]-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)OC4C(C(C(C(O4)CO)O)O)O)C5=CC=C(C=C5)O)C6=C7C(C(OC7=CC(=C6)O)C8=CC=C(C=C8)O)C9=CC(=CC(=C9)OC1C(C(C(C(O1)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C\C2=C3[C@H]([C@@H](OC3=CC(=C2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=CC=C(C=C5)O)C6=C7[C@H]([C@H](OC7=CC(=C6)O)C8=CC=C(C=C8)O)C9=CC(=CC(=C9)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O
• InChI: InChI=1S/C54H52O19/c55-22-39-45(62)47(64)49(66)53(72-39)68-34-17-28(15-32(60)18-34)42-43-36(19-33(61)20-37(43)70-51(42)25-5-11-30(58)12-6-25)44-41-27(4-1-24-2-9-29(57)10-3-24)16-35(69-54-50(67)48(65)46(63)40(23-56)73-54)21-38(41)71-52(44)26-7-13-31(59)14-8-26/h1-21,39-40,42,44-67H,22-23H2/b4-1-/t39-,40-,42-,44-,45-,46-,47+,48+,49-,50-,51-,52+,53-,54-/m1/s1
• InChI Key: VKKUIYOSAFMZQL-ZWYVWNPHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₅₂O₁₉
• Molecular Weight: 1005.00 g/mol
• Exact Mass: 1004.31027942 g/mol
• Topological Polar Surface Area (TPSA): 318.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.27
• H-Bond Acceptor: 19
• H-Bond Donor: 13
• Rotatable Bonds: 12

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	-	0.8835	88.35%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6106	61.06%
OATP2B1 inhibitior	-	0.8488	84.88%
OATP1B1 inhibitior	+	0.8241	82.41%
OATP1B3 inhibitior	+	0.9649	96.49%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8858	88.58%
P-glycoprotein inhibitior	+	0.6947	69.47%
P-glycoprotein substrate	-	0.7008	70.08%
CYP3A4 substrate	+	0.6511	65.11%
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	+	0.7960	79.60%
CYP inhibitory promiscuity	+	0.6287	62.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5320	53.20%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.8942	89.42%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8933	89.33%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.8019	80.19%
skin sensitisation	-	0.8530	85.30%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7168	71.68%
Acute Oral Toxicity (c)	III	0.5369	53.69%
Estrogen receptor binding	+	0.7770	77.70%
Androgen receptor binding	+	0.6779	67.79%
Thyroid receptor binding	+	0.5554	55.54%
Glucocorticoid receptor binding	-	0.5221	52.21%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7456	74.56%
Honey bee toxicity	-	0.6550	65.50%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
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	99.67%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.89%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.18%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	92.26%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.09%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.12%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.87%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.62%	89.00%
CHEMBL3194	P02766	Transthyretin	90.37%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	89.61%	98.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.36%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.34%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.91%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.80%	99.15%
CHEMBL226	P30542	Adenosine A1 receptor	85.87%	95.93%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.83%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.79%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.85%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.36%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.70%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.35%	89.67%

Plants that contains it

• Foeniculum vulgare

Cross-Links

• PubChem: 154496577
• LOTUS: LTS0086979
• wikiData: Q105287833