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

Details

• Internal ID: 4c4164b7-e278-4637-98cb-99977d7c98e0
• 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-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)CC2COC(C2COC3C(C(C(C(O3)COC(=O)C=CC4=CC(=C(C=C4)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)O)OC)O)O)O)C5=CC(=C(C(=C5)OC)O)OC
• InChI: InChI=1S/C38H46O16/c1-46-25-11-19(6-8-24(25)39)7-9-31(40)51-18-30-34(43)35(44)36(45)38(54-30)53-17-23-22(10-20-12-26(47-2)32(41)27(13-20)48-3)16-52-37(23)21-14-28(49-4)33(42)29(15-21)50-5/h6-9,11-15,22-23,30,34-39,41-45H,10,16-18H2,1-5H3/b9-7+/t22-,23-,30+,34+,35-,36+,37+,38+/m0/s1
• InChI Key: WQGFZONMTGYTJZ-LJYSTODUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₆O₁₆
• Molecular Weight: 758.80 g/mol
• Exact Mass: 758.27858538 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 16
• H-Bond Donor: 6
• Rotatable Bonds: 15

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	-	0.8709	87.09%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8263	82.63%
OATP2B1 inhibitior	-	0.5744	57.44%
OATP1B1 inhibitior	+	0.8250	82.50%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7393	73.93%
P-glycoprotein inhibitior	+	0.7571	75.71%
P-glycoprotein substrate	-	0.5342	53.42%
CYP3A4 substrate	+	0.6857	68.57%
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	+	0.8040	80.40%
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	-	0.9180	91.80%
Skin irritation	-	0.8554	85.54%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7345	73.45%
Micronuclear	+	0.5674	56.74%
Hepatotoxicity	-	0.7091	70.91%
skin sensitisation	-	0.8510	85.10%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9716	97.16%
Acute Oral Toxicity (c)	III	0.6385	63.85%
Estrogen receptor binding	+	0.8122	81.22%
Androgen receptor binding	+	0.6892	68.92%
Thyroid receptor binding	+	0.5530	55.30%
Glucocorticoid receptor binding	+	0.7011	70.11%
Aromatase binding	+	0.5682	56.82%
PPAR gamma	+	0.6921	69.21%
Honey bee toxicity	-	0.7714	77.14%
Biodegradation	-	0.7750	77.50%
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	99.84%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.02%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.01%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.38%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.25%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.51%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.54%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.30%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.28%	99.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.36%	96.61%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.32%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.21%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.95%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.69%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	87.53%	94.73%
CHEMBL3194	P02766	Transthyretin	87.12%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.16%	95.89%
CHEMBL4208	P20618	Proteasome component C5	84.07%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.11%	95.89%

Plants that contains it

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

Cross-Links

• PubChem: 102408527
• NPASS: NPC47922
• LOTUS: LTS0243382
• wikiData: Q105310698