(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-methoxy-4-prop-2-enyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol

Details

• Internal ID: 8b612567-0b8c-4707-95a5-a98ef8a55e87
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-methoxy-4-prop-2-enyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C(=CC(=C1)CC=C)OC2C(C(C(C(O2)COC3C(C(C(CO3)O)O)O)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C(C(=CC(=C1)CC=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C27H40O17/c1-3-4-10-5-12(38-2)24(44-27-23(37)19(33)17(31)14(7-28)42-27)13(6-10)41-26-22(36)20(34)18(32)15(43-26)9-40-25-21(35)16(30)11(29)8-39-25/h3,5-6,11,14-23,25-37H,1,4,7-9H2,2H3/t11-,14+,15+,16-,17+,18+,19-,20-,21+,22+,23+,25-,26+,27-/m0/s1
• InChI Key: SVDWENSOHYWMAU-LDSJIWQESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₁₇
• Molecular Weight: 636.60 g/mol
• Exact Mass: 636.22654980 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -3.40
• Atomic LogP (AlogP): -4.76
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7697	76.97%
Caco-2	-	0.8946	89.46%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5603	56.03%
OATP2B1 inhibitior	-	0.8643	86.43%
OATP1B1 inhibitior	+	0.8515	85.15%
OATP1B3 inhibitior	+	0.9665	96.65%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8006	80.06%
P-glycoprotein inhibitior	-	0.5304	53.04%
P-glycoprotein substrate	-	0.6722	67.22%
CYP3A4 substrate	+	0.6277	62.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7725	77.25%
CYP3A4 inhibition	-	0.8278	82.78%
CYP2C9 inhibition	-	0.9143	91.43%
CYP2C19 inhibition	-	0.8859	88.59%
CYP2D6 inhibition	-	0.8774	87.74%
CYP1A2 inhibition	-	0.9082	90.82%
CYP2C8 inhibition	+	0.5941	59.41%
CYP inhibitory promiscuity	-	0.8710	87.10%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9275	92.75%
Skin irritation	-	0.8219	82.19%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8293	82.93%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.7947	79.47%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.8956	89.56%
Acute Oral Toxicity (c)	III	0.7594	75.94%
Estrogen receptor binding	+	0.7363	73.63%
Androgen receptor binding	-	0.6426	64.26%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5121	51.21%
Aromatase binding	+	0.6127	61.27%
PPAR gamma	+	0.6635	66.35%
Honey bee toxicity	-	0.7335	73.35%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.7257	72.57%

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%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.33%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.06%	99.17%
CHEMBL226	P30542	Adenosine A1 receptor	89.87%	95.93%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.81%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.68%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.25%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.56%	85.14%
CHEMBL2581	P07339	Cathepsin D	86.11%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.89%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.02%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.90%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.76%	97.09%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	84.49%	97.88%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.55%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.45%	97.25%
CHEMBL4208	P20618	Proteasome component C5	81.67%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	81.30%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.08%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.02%	95.83%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.54%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.06%	94.00%

Plants that contains it

• Adenophora triphylla

Cross-Links

• PubChem: 15714548
• LOTUS: LTS0082012
• wikiData: Q105261890