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

Details

• Internal ID: c977f2e3-62c2-40a5-8bb1-44fae43ea649
• 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-methoxyphenyl)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)C2C(C(CO2)CC3=CC(=C(C=C3)O)OC)COC4C(C(C(C(O4)COC(=O)C=CC5=CC(=C(C=C5)O)OC)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H]([C@H](CO2)CC3=CC(=C(C=C3)O)OC)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)/C=C/C5=CC(=C(C=C5)O)OC)O)O)O
• InChI: InChI=1S/C37H44O15/c1-45-26-12-19(5-8-24(26)38)7-10-31(40)49-18-30-33(42)34(43)35(44)37(52-30)51-17-23-22(11-20-6-9-25(39)27(13-20)46-2)16-50-36(23)21-14-28(47-3)32(41)29(15-21)48-4/h5-10,12-15,22-23,30,33-39,41-44H,11,16-18H2,1-4H3/b10-7+/t22-,23-,30+,33+,34-,35+,36+,37+/m0/s1
• InChI Key: QIVBVEZLUWGMPA-CJBVJWGFSA-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	-	0.8738	87.38%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8263	82.63%
OATP2B1 inhibitior	-	0.5751	57.51%
OATP1B1 inhibitior	+	0.8278	82.78%
OATP1B3 inhibitior	+	0.9457	94.57%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7823	78.23%
P-glycoprotein inhibitior	+	0.7549	75.49%
P-glycoprotein substrate	-	0.5165	51.65%
CYP3A4 substrate	+	0.6866	68.66%
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	+	0.8275	82.75%
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	-	0.9200	92.00%
Skin irritation	-	0.8554	85.54%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7528	75.28%
Micronuclear	+	0.5674	56.74%
Hepatotoxicity	-	0.7341	73.41%
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	-	0.9821	98.21%
Acute Oral Toxicity (c)	III	0.6385	63.85%
Estrogen receptor binding	+	0.8088	80.88%
Androgen receptor binding	+	0.6990	69.90%
Thyroid receptor binding	+	0.5503	55.03%
Glucocorticoid receptor binding	+	0.6955	69.55%
Aromatase binding	+	0.5243	52.43%
PPAR gamma	+	0.6733	67.33%
Honey bee toxicity	-	0.7626	76.26%
Biodegradation	-	0.7500	75.00%
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	99.85%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.00%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.86%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.48%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.57%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.25%	96.61%
CHEMBL2581	P07339	Cathepsin D	93.89%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.74%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.76%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.95%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.95%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.72%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.48%	95.56%
CHEMBL3194	P02766	Transthyretin	87.24%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.42%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.21%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	86.12%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.31%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.37%	89.62%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.13%	80.78%
CHEMBL4208	P20618	Proteasome component C5	82.74%	90.00%

Plants that contains it

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

Cross-Links

• PubChem: 102408533
• NPASS: NPC47331
• LOTUS: LTS0213144
• wikiData: Q105222417