(2S,3R,4S,5S,6R)-2-[5-hydroxy-3-[(E)-2-(4-hydroxyphenyl)ethenyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 0142af6c-b1f8-453a-80ab-a8e8d4d7f05d
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[5-hydroxy-3-[(E)-2-(4-hydroxyphenyl)ethenyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(=CC=C1C=CC2=C(C(=CC(=C2)O)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C/C2=C(C(=CC(=C2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H32O14/c27-9-16-18(31)20(33)22(35)25(38-16)37-15-8-14(30)7-12(4-1-11-2-5-13(29)6-3-11)24(15)40-26-23(36)21(34)19(32)17(10-28)39-26/h1-8,16-23,25-36H,9-10H2/b4-1+/t16-,17-,18-,19-,20+,21+,22-,23-,25-,26+/m1/s1
• InChI Key: JIDQTNPRNYPBCR-NOAXIPAFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₄
• Molecular Weight: 568.50 g/mol
• Exact Mass: 568.17920569 g/mol
• Topological Polar Surface Area (TPSA): 239.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -2.37
• H-Bond Acceptor: 14
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8398	83.98%
Caco-2	-	0.9171	91.71%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5500	55.00%
OATP2B1 inhibitior	-	0.5679	56.79%
OATP1B1 inhibitior	+	0.8785	87.85%
OATP1B3 inhibitior	+	0.9663	96.63%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5564	55.64%
P-glycoprotein inhibitior	-	0.6092	60.92%
P-glycoprotein substrate	-	0.9032	90.32%
CYP3A4 substrate	+	0.5131	51.31%
CYP2C9 substrate	+	0.5811	58.11%
CYP2D6 substrate	-	0.8191	81.91%
CYP3A4 inhibition	-	0.9180	91.80%
CYP2C9 inhibition	-	0.8946	89.46%
CYP2C19 inhibition	-	0.8435	84.35%
CYP2D6 inhibition	-	0.8871	88.71%
CYP1A2 inhibition	-	0.9318	93.18%
CYP2C8 inhibition	+	0.7069	70.69%
CYP inhibitory promiscuity	-	0.6530	65.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6312	63.12%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.8787	87.87%
Skin irritation	-	0.8468	84.68%
Skin corrosion	-	0.9637	96.37%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7561	75.61%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	-	0.9050	90.50%
skin sensitisation	-	0.8030	80.30%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.7500	75.00%
Nephrotoxicity	-	0.6238	62.38%
Acute Oral Toxicity (c)	III	0.5907	59.07%
Estrogen receptor binding	+	0.6863	68.63%
Androgen receptor binding	+	0.5929	59.29%
Thyroid receptor binding	+	0.6009	60.09%
Glucocorticoid receptor binding	-	0.6203	62.03%
Aromatase binding	+	0.6730	67.30%
PPAR gamma	+	0.7126	71.26%
Honey bee toxicity	-	0.7923	79.23%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8165	81.65%

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	98.98%	91.11%
CHEMBL3194	P02766	Transthyretin	95.89%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.62%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.63%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	91.35%	98.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.75%	86.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.73%	89.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.08%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.24%	89.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	88.17%	89.67%
CHEMBL3401	O75469	Pregnane X receptor	86.82%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	85.04%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.08%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.93%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.33%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.23%	83.57%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.11%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.89%	95.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.61%	91.71%

Plants that contains it

• Rheum palmatum
• Rheum tanguticum

Cross-Links

• PubChem: 5321886
• NPASS: NPC260681