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

Details

• Internal ID: 954c73f0-b69e-4c55-a56e-2dfd5e76ad05
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-4-hydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-2-yl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=CC(=C3C(C(OC3=C2)C4=CC=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)C6=CC(=CC(=C6)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=CC(=C3[C@@H]([C@H](OC3=C2)C4=CC=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C6=CC(=CC(=C6)O)O)O)O
• InChI: InChI=1S/C34H32O11/c35-16-27-30(40)31(41)32(42)34(45-27)43-24-9-5-19(6-10-24)33-28(20-13-22(37)15-23(38)14-20)29-25(39)11-18(12-26(29)44-33)2-1-17-3-7-21(36)8-4-17/h1-15,27-28,30-42H,16H2/b2-1+/t27-,28+,30-,31+,32-,33-,34-/m1/s1
• InChI Key: QSENDESKKUIXHU-HJTPYMFFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₃₂O₁₁
• Molecular Weight: 616.60 g/mol
• Exact Mass: 616.19446183 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.12
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• SCHEMBL15939640

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6558	65.58%
Caco-2	-	0.9009	90.09%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6186	61.86%
OATP2B1 inhibitior	+	0.5682	56.82%
OATP1B1 inhibitior	+	0.8643	86.43%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8188	81.88%
P-glycoprotein inhibitior	+	0.6421	64.21%
P-glycoprotein substrate	-	0.8198	81.98%
CYP3A4 substrate	+	0.6230	62.30%
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	+	0.7549	75.49%
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	-	0.8665	86.65%
Skin irritation	-	0.7987	79.87%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	+	0.5163	51.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7679	76.79%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.8675	86.75%
skin sensitisation	-	0.8497	84.97%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5803	58.03%
Acute Oral Toxicity (c)	III	0.5167	51.67%
Estrogen receptor binding	+	0.7016	70.16%
Androgen receptor binding	+	0.6716	67.16%
Thyroid receptor binding	+	0.6175	61.75%
Glucocorticoid receptor binding	+	0.6028	60.28%
Aromatase binding	-	0.4925	49.25%
PPAR gamma	+	0.7359	73.59%
Honey bee toxicity	-	0.7227	72.27%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
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	99.60%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.97%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.48%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	94.90%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.06%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	91.82%	94.73%
CHEMBL3194	P02766	Transthyretin	91.52%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.51%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.42%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.09%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.40%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.67%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.83%	99.15%
CHEMBL4208	P20618	Proteasome component C5	86.35%	90.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.89%	91.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.80%	86.33%
CHEMBL2581	P07339	Cathepsin D	84.82%	98.95%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.66%	89.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.47%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.08%	97.33%

Plants that contains it

• Gnetum gnemon

Cross-Links

• PubChem: 21633860
• LOTUS: LTS0031015
• wikiData: Q105226909