[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

Details

• Internal ID: 0b35aa8c-008b-40c9-a36d-c9868da8ac11
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C(=O)OCC2C(C(C(C(O2)OC3=CC(=CC(=C3)O)C=CC4=CC=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=CC(=C3)O)/C=C/C4=CC=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C28H28O11/c1-36-22-12-17(6-9-21(22)31)27(35)37-14-23-24(32)25(33)26(34)28(39-23)38-20-11-16(10-19(30)13-20)3-2-15-4-7-18(29)8-5-15/h2-13,23-26,28-34H,14H2,1H3/b3-2+/t23-,24-,25+,26-,28-/m1/s1
• InChI Key: JFCVAWLHDBBPMF-LZRUTRTESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₈O₁₁
• Molecular Weight: 540.50 g/mol
• Exact Mass: 540.16316171 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5698	56.98%
Caco-2	-	0.8891	88.91%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6589	65.89%
OATP2B1 inhibitior	-	0.7064	70.64%
OATP1B1 inhibitior	+	0.8904	89.04%
OATP1B3 inhibitior	+	0.9553	95.53%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7997	79.97%
P-glycoprotein inhibitior	+	0.6319	63.19%
P-glycoprotein substrate	-	0.7854	78.54%
CYP3A4 substrate	+	0.6125	61.25%
CYP2C9 substrate	-	0.6162	61.62%
CYP2D6 substrate	-	0.8400	84.00%
CYP3A4 inhibition	-	0.7952	79.52%
CYP2C9 inhibition	-	0.8076	80.76%
CYP2C19 inhibition	-	0.8058	80.58%
CYP2D6 inhibition	-	0.8832	88.32%
CYP1A2 inhibition	-	0.8061	80.61%
CYP2C8 inhibition	+	0.8518	85.18%
CYP inhibitory promiscuity	-	0.5450	54.50%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7030	70.30%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8896	88.96%
Skin irritation	-	0.8167	81.67%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4365	43.65%
Micronuclear	+	0.6866	68.66%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8544	85.44%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.8422	84.22%
Acute Oral Toxicity (c)	III	0.7643	76.43%
Estrogen receptor binding	+	0.7413	74.13%
Androgen receptor binding	+	0.6098	60.98%
Thyroid receptor binding	+	0.5900	59.00%
Glucocorticoid receptor binding	+	0.6831	68.31%
Aromatase binding	-	0.5423	54.23%
PPAR gamma	+	0.6321	63.21%
Honey bee toxicity	-	0.8060	80.60%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9020	90.20%

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	98.53%	91.11%
CHEMBL3194	P02766	Transthyretin	97.31%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.83%	96.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	94.84%	85.31%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.50%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.28%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.02%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.07%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	90.71%	94.73%
CHEMBL4208	P20618	Proteasome component C5	89.53%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.03%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.64%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.85%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.76%	95.89%
CHEMBL2535	P11166	Glucose transporter	82.54%	98.75%
CHEMBL5255	O00206	Toll-like receptor 4	81.38%	92.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.04%	96.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.17%	90.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.14%	94.33%

Plants that contains it

• Lysidice brevicalyx

Cross-Links

• PubChem: 163188986
• LOTUS: LTS0272883
• wikiData: Q105126604