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

Details

• Internal ID: 6d645893-38af-4f95-956d-625a18d7cf0c
• 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-hydroxyphenyl)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)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)O)O)O)C5=CC(=C(C(=C5)OC)O)OC
• InChI: InChI=1S/C37H44O15/c1-45-25-12-20(13-26(46-2)31(25)40)11-22-16-50-36(21-14-27(47-3)32(41)28(15-21)48-4)24(22)17-51-37-35(44)34(43)33(42)29(52-37)18-49-30(39)10-7-19-5-8-23(38)9-6-19/h5-10,12-15,22,24,29,33-38,40-44H,11,16-18H2,1-4H3/b10-7+/t22-,24-,29+,33+,34-,35+,36+,37+/m0/s1
• InChI Key: KKCYUJUITAANCB-WWCCTYCASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₄O₁₅
• Molecular Weight: 728.70 g/mol
• Exact Mass: 728.26802069 g/mol
• Topological Polar Surface Area (TPSA): 212.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 14

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	-	0.8729	87.29%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8263	82.63%
OATP2B1 inhibitior	-	0.7135	71.35%
OATP1B1 inhibitior	+	0.7965	79.65%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6799	67.99%
P-glycoprotein inhibitior	+	0.7464	74.64%
P-glycoprotein substrate	+	0.5228	52.28%
CYP3A4 substrate	+	0.6935	69.35%
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	+	0.8362	83.62%
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	-	0.9194	91.94%
Skin irritation	-	0.8554	85.54%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7185	71.85%
Micronuclear	+	0.5674	56.74%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8510	85.10%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.9402	94.02%
Acute Oral Toxicity (c)	III	0.6385	63.85%
Estrogen receptor binding	+	0.8271	82.71%
Androgen receptor binding	+	0.7087	70.87%
Thyroid receptor binding	+	0.5424	54.24%
Glucocorticoid receptor binding	+	0.6926	69.26%
Aromatase binding	+	0.5577	55.77%
PPAR gamma	+	0.6724	67.24%
Honey bee toxicity	-	0.7541	75.41%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
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	99.54%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.06%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.43%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.97%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.70%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	94.43%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.76%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.48%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.30%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.70%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.85%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.66%	89.62%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.48%	89.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.27%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.66%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	85.64%	94.73%
CHEMBL3194	P02766	Transthyretin	83.90%	90.71%
CHEMBL4208	P20618	Proteasome component C5	83.65%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.60%	95.89%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.79%	89.44%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.77%	90.71%

Plants that contains it

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

Cross-Links

• PubChem: 102408531
• NPASS: NPC226407
• LOTUS: LTS0258796
• wikiData: Q105142138