(2S,3R,4S,5S,6R)-2-[4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-3-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 810b60c9-c1b2-4c40-ad88-44941f54680d
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-3-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=C(C=C1OC2C(C(C(C(O2)CO)O)O)O)O)C=CC3=CC(=CC(=C3)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)/C=C/C3=CC(=CC(=C3)O)O
• InChI: InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-14-4-3-11(15(24)8-14)2-1-10-5-12(22)7-13(23)6-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
• InChI Key: QNJXAEVGLMVYJF-CUYWLFDKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₉
• Molecular Weight: 406.40 g/mol
• Exact Mass: 406.12638228 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

• HY-N12081
• CS-0891521

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7283	72.83%
Caco-2	-	0.9235	92.35%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5553	55.53%
OATP2B1 inhibitior	+	0.5733	57.33%
OATP1B1 inhibitior	+	0.9340	93.40%
OATP1B3 inhibitior	+	0.9568	95.68%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5946	59.46%
P-glycoprotein inhibitior	-	0.8184	81.84%
P-glycoprotein substrate	-	0.9532	95.32%
CYP3A4 substrate	+	0.5066	50.66%
CYP2C9 substrate	+	0.5811	58.11%
CYP2D6 substrate	-	0.8191	81.91%
CYP3A4 inhibition	-	0.8471	84.71%
CYP2C9 inhibition	-	0.8424	84.24%
CYP2C19 inhibition	-	0.8155	81.55%
CYP2D6 inhibition	-	0.9002	90.02%
CYP1A2 inhibition	-	0.9137	91.37%
CYP2C8 inhibition	+	0.5528	55.28%
CYP inhibitory promiscuity	-	0.5561	55.61%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6854	68.54%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.8312	83.12%
Skin irritation	-	0.8338	83.38%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4617	46.17%
Micronuclear	+	0.5359	53.59%
Hepatotoxicity	-	0.8550	85.50%
skin sensitisation	-	0.7594	75.94%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.6227	62.27%
Acute Oral Toxicity (c)	III	0.6964	69.64%
Estrogen receptor binding	+	0.6137	61.37%
Androgen receptor binding	-	0.5436	54.36%
Thyroid receptor binding	+	0.6832	68.32%
Glucocorticoid receptor binding	-	0.4898	48.98%
Aromatase binding	+	0.6745	67.45%
PPAR gamma	+	0.8476	84.76%
Honey bee toxicity	-	0.7827	78.27%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8707	87.07%

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	99.61%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.95%	91.49%
CHEMBL3194	P02766	Transthyretin	95.14%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.56%	96.00%
CHEMBL226	P30542	Adenosine A1 receptor	92.16%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	91.49%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.44%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.34%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.02%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.62%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.40%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.99%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.72%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.60%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.63%	99.15%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.99%	83.57%
CHEMBL4208	P20618	Proteasome component C5	85.92%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.82%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.54%	95.83%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.44%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.38%	91.71%
CHEMBL2581	P07339	Cathepsin D	82.87%	98.95%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	81.24%	88.00%

Plants that contains it

• Veratrum dahuricum

Cross-Links

• PubChem: 163195593
• LOTUS: LTS0173784
• wikiData: Q105224511