(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-methoxy-5-[2-(4-methoxyphenyl)ethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol

Details

• Internal ID: cd5a22dc-0cdf-490e-a910-32b21c5ad00b
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-methoxy-5-[2-(4-methoxyphenyl)ethyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC=C(C=C1)CCC2=CC(=C(C(=C2)OC3C(C(C(C(O3)CO)O)O)O)OC4C(C(C(C(O4)CO)O)O)O)OC
• SMILES (Isomeric): COC1=CC=C(C=C1)CCC2=CC(=C(C(=C2)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)OC
• InChI: InChI=1S/C28H38O14/c1-37-15-7-5-13(6-8-15)3-4-14-9-16(38-2)26(42-28-25(36)23(34)21(32)19(12-30)41-28)17(10-14)39-27-24(35)22(33)20(31)18(11-29)40-27/h5-10,18-25,27-36H,3-4,11-12H2,1-2H3/t18-,19-,20-,21-,22+,23+,24-,25-,27-,28+/m1/s1
• InChI Key: IUHPHRNJNAEZNF-CNTQWYRWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₁₄
• Molecular Weight: 598.60 g/mol
• Exact Mass: 598.22615588 g/mol
• Topological Polar Surface Area (TPSA): 217.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -2.15
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8829	88.29%
Caco-2	-	0.8737	87.37%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7153	71.53%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.8871	88.71%
OATP1B3 inhibitior	+	0.9594	95.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5347	53.47%
P-glycoprotein inhibitior	-	0.5328	53.28%
P-glycoprotein substrate	-	0.7400	74.00%
CYP3A4 substrate	+	0.5846	58.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7653	76.53%
CYP3A4 inhibition	-	0.9548	95.48%
CYP2C9 inhibition	-	0.7761	77.61%
CYP2C19 inhibition	-	0.8715	87.15%
CYP2D6 inhibition	-	0.9220	92.20%
CYP1A2 inhibition	-	0.8845	88.45%
CYP2C8 inhibition	+	0.6748	67.48%
CYP inhibitory promiscuity	-	0.7935	79.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6889	68.89%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9355	93.55%
Skin irritation	-	0.8494	84.94%
Skin corrosion	-	0.9569	95.69%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7370	73.70%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8941	89.41%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.8549	85.49%
Acute Oral Toxicity (c)	III	0.7868	78.68%
Estrogen receptor binding	+	0.7952	79.52%
Androgen receptor binding	+	0.5201	52.01%
Thyroid receptor binding	+	0.5243	52.43%
Glucocorticoid receptor binding	-	0.5149	51.49%
Aromatase binding	+	0.5306	53.06%
PPAR gamma	+	0.6576	65.76%
Honey bee toxicity	-	0.8107	81.07%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	-	0.5922	59.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.40%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.41%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.73%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	94.01%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.21%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.75%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.55%	85.14%
CHEMBL4208	P20618	Proteasome component C5	89.08%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.26%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.14%	92.62%
CHEMBL2581	P07339	Cathepsin D	87.74%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.68%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.82%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.86%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.62%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.96%	95.50%
CHEMBL2535	P11166	Glucose transporter	80.93%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	80.93%	94.73%

Plants that contains it

• Dendrobium moniliforme

Cross-Links

• PubChem: 162914885
• LOTUS: LTS0068449
• wikiData: Q105120558