(2S)-2alpha-(3,5-Dimethoxy-4-hydroxyphenyl)-3beta-[6-O-[(E)-3-(3,5-dimethoxy-4-hydroxyphenyl)acryloyl]-beta-D-glucopyranosyloxymethyl]-4beta-(3,5-dimethoxy-4-hydroxybenzyl)tetrahydrofuran

Details

• Internal ID: 24260fb7-8961-4984-8ba1-777d9bf9e064
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]oxolan-3-yl]methoxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)CC2COC(C2COC3C(C(C(C(O3)COC(=O)C=CC4=CC(=C(C(=C4)OC)O)OC)O)O)O)C5=CC(=C(C(=C5)OC)O)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C[C@H]2CO[C@@H]([C@H]2CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC(=C(C(=C4)OC)O)OC)O)O)O)C5=CC(=C(C(=C5)OC)O)OC
• InChI: InChI=1S/C39H48O17/c1-47-24-10-19(11-25(48-2)32(24)41)7-8-31(40)53-18-30-35(44)36(45)37(46)39(56-30)55-17-23-22(9-20-12-26(49-3)33(42)27(13-20)50-4)16-54-38(23)21-14-28(51-5)34(43)29(15-21)52-6/h7-8,10-15,22-23,30,35-39,41-46H,9,16-18H2,1-6H3/b8-7+/t22-,23-,30+,35+,36-,37+,38+,39+/m0/s1
• InChI Key: MUMASVOACPGOAP-FAHWLZQFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₈O₁₇
• Molecular Weight: 788.80 g/mol
• Exact Mass: 788.28915006 g/mol
• Topological Polar Surface Area (TPSA): 231.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.48
• H-Bond Acceptor: 17
• H-Bond Donor: 6
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5580	55.80%
Caco-2	-	0.8679	86.79%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8263	82.63%
OATP2B1 inhibitior	-	0.5740	57.40%
OATP1B1 inhibitior	+	0.7966	79.66%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7783	77.83%
P-glycoprotein inhibitior	+	0.7616	76.16%
P-glycoprotein substrate	-	0.5384	53.84%
CYP3A4 substrate	+	0.6787	67.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8591	85.91%
CYP3A4 inhibition	-	0.7336	73.36%
CYP2C9 inhibition	-	0.7904	79.04%
CYP2C19 inhibition	-	0.6864	68.64%
CYP2D6 inhibition	-	0.9056	90.56%
CYP1A2 inhibition	-	0.8693	86.93%
CYP2C8 inhibition	+	0.7218	72.18%
CYP inhibitory promiscuity	+	0.6174	61.74%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6140	61.40%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9136	91.36%
Skin irritation	-	0.8554	85.54%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7120	71.20%
Micronuclear	+	0.5674	56.74%
Hepatotoxicity	-	0.7216	72.16%
skin sensitisation	-	0.8510	85.10%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9438	94.38%
Acute Oral Toxicity (c)	III	0.6385	63.85%
Estrogen receptor binding	+	0.7977	79.77%
Androgen receptor binding	+	0.6475	64.75%
Thyroid receptor binding	+	0.5496	54.96%
Glucocorticoid receptor binding	+	0.7083	70.83%
Aromatase binding	+	0.5907	59.07%
PPAR gamma	+	0.6906	69.06%
Honey bee toxicity	-	0.7572	75.72%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9821	98.21%

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	99.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.96%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.82%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.13%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.87%	96.00%
CHEMBL2581	P07339	Cathepsin D	94.05%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.93%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.70%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.02%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.98%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	89.31%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.03%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.86%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.91%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.19%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	84.63%	92.50%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.68%	85.31%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.05%	97.36%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Hyperbaena columbica
• Viburnum lantanoides

Cross-Links

• PubChem: 102408532
• NPASS: NPC150305
• LOTUS: LTS0185713
• wikiData: Q105172534