[(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2-hydroxy-6-(3-hydroxyphenyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate

Details

• Internal ID: 487bfddf-a23f-4cc6-ac59-254ba495c7ed
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2-hydroxy-6-(3-hydroxyphenyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• SMILES (Canonical): C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)OC(=O)C4=C(C=C(C=C4O)OC5C(C(C(C(O5)CO)O)O)O)C6=CC(=CC=C6)O
• SMILES (Isomeric): C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C4=C(C=C(C=C4O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C6=CC(=CC=C6)O
• InChI: InChI=1S/C35H40O18/c1-2-17-18-6-7-47-31(45)20(18)13-48-33(17)53-35-30(28(43)26(41)23(12-37)51-35)52-32(46)24-19(14-4-3-5-15(38)8-14)9-16(10-21(24)39)49-34-29(44)27(42)25(40)22(11-36)50-34/h2-5,8-10,13,17-18,22-23,25-30,33-44H,1,6-7,11-12H2/t17-,18+,22-,23-,25-,26-,27+,28+,29-,30-,33+,34-,35+/m1/s1
• InChI Key: NDBQDSDNBBHTIX-DNVPPJTJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₀O₁₈
• Molecular Weight: 748.70 g/mol
• Exact Mass: 748.22146442 g/mol
• Topological Polar Surface Area (TPSA): 281.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -1.47
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4645	46.45%
Caco-2	-	0.8998	89.98%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7196	71.96%
OATP2B1 inhibitior	-	0.7117	71.17%
OATP1B1 inhibitior	+	0.8404	84.04%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6104	61.04%
P-glycoprotein inhibitior	+	0.6415	64.15%
P-glycoprotein substrate	-	0.5089	50.89%
CYP3A4 substrate	+	0.7061	70.61%
CYP2C9 substrate	-	0.6129	61.29%
CYP2D6 substrate	-	0.8656	86.56%
CYP3A4 inhibition	-	0.8842	88.42%
CYP2C9 inhibition	-	0.6727	67.27%
CYP2C19 inhibition	-	0.7393	73.93%
CYP2D6 inhibition	-	0.8756	87.56%
CYP1A2 inhibition	-	0.7478	74.78%
CYP2C8 inhibition	+	0.7809	78.09%
CYP inhibitory promiscuity	-	0.7630	76.30%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6864	68.64%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.9010	90.10%
Skin irritation	-	0.7960	79.60%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7286	72.86%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	-	0.6976	69.76%
skin sensitisation	-	0.8205	82.05%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6570	65.70%
Acute Oral Toxicity (c)	III	0.4552	45.52%
Estrogen receptor binding	+	0.8198	81.98%
Androgen receptor binding	+	0.6798	67.98%
Thyroid receptor binding	-	0.4903	49.03%
Glucocorticoid receptor binding	-	0.4680	46.80%
Aromatase binding	+	0.5285	52.85%
PPAR gamma	+	0.7276	72.76%
Honey bee toxicity	-	0.6849	68.49%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9645	96.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.20%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.06%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.43%	97.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	96.05%	83.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.29%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.01%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.75%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.52%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.09%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.81%	95.89%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	88.71%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	88.67%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.99%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.26%	94.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.97%	95.83%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.63%	91.24%
CHEMBL220	P22303	Acetylcholinesterase	83.48%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.36%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.33%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.19%	100.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.60%	94.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.37%	97.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.32%	95.78%
CHEMBL340	P08684	Cytochrome P450 3A4	82.22%	91.19%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	82.18%	96.11%
CHEMBL3401	O75469	Pregnane X receptor	81.99%	94.73%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.28%	94.80%
CHEMBL4530	P00488	Coagulation factor XIII	80.26%	96.00%

Plants that contains it

• Swertia japonica

Cross-Links

• PubChem: 101727263
• LOTUS: LTS0266844
• wikiData: Q105177471