[(2R,3S,4S,5R,6S)-6-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: ef943859-3b00-4b56-8e06-950529b10241
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2=C(C=C(C=C2O)O)C=CC3=CC=C(C=C3)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=C(C=C(C=C2O)O)/C=C/C3=CC=C(C=C3)O)O)O)O
• InChI: InChI=1S/C22H24O10/c1-11(23)30-10-17-18(27)19(28)20(29)22(31-17)32-21-13(8-15(25)9-16(21)26)5-2-12-3-6-14(24)7-4-12/h2-9,17-20,22,24-29H,10H2,1H3/b5-2+/t17-,18-,19+,20-,22+/m1/s1
• InChI Key: NDTPPCMMWLHFIY-GJSUQYHZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄O₁₀
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.13694696 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• BDBM50537876

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5866	58.66%
Caco-2	-	0.8877	88.77%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7207	72.07%
OATP2B1 inhibitior	+	0.5740	57.40%
OATP1B1 inhibitior	+	0.8503	85.03%
OATP1B3 inhibitior	+	0.9340	93.40%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8406	84.06%
P-glycoprotein inhibitior	-	0.5346	53.46%
P-glycoprotein substrate	-	0.8780	87.80%
CYP3A4 substrate	+	0.5909	59.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8766	87.66%
CYP3A4 inhibition	-	0.8505	85.05%
CYP2C9 inhibition	-	0.8199	81.99%
CYP2C19 inhibition	-	0.8435	84.35%
CYP2D6 inhibition	-	0.8892	88.92%
CYP1A2 inhibition	-	0.7320	73.20%
CYP2C8 inhibition	+	0.6676	66.76%
CYP inhibitory promiscuity	-	0.5275	52.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7382	73.82%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.8636	86.36%
Skin irritation	-	0.7928	79.28%
Skin corrosion	-	0.9451	94.51%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3622	36.22%
Micronuclear	+	0.5466	54.66%
Hepatotoxicity	-	0.8050	80.50%
skin sensitisation	-	0.8139	81.39%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7118	71.18%
Acute Oral Toxicity (c)	III	0.7496	74.96%
Estrogen receptor binding	+	0.7169	71.69%
Androgen receptor binding	+	0.6136	61.36%
Thyroid receptor binding	+	0.5611	56.11%
Glucocorticoid receptor binding	-	0.4914	49.14%
Aromatase binding	-	0.5508	55.08%
PPAR gamma	+	0.6421	64.21%
Honey bee toxicity	-	0.8262	82.62%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6455	64.55%
Fish aquatic toxicity	+	0.9735	97.35%

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	99.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.33%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.68%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	94.43%	94.73%
CHEMBL3194	P02766	Transthyretin	93.65%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.16%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.43%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.45%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	91.44%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.47%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.84%	98.95%
CHEMBL4208	P20618	Proteasome component C5	84.37%	90.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.29%	95.64%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.73%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.48%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.13%	89.62%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.52%	89.67%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.07%	94.80%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.01%	97.21%

Plants that contains it

• Hypericum japonicum

Cross-Links

• PubChem: 11968988
• NPASS: NPC199977