(2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-3-(3,4-dihydroxy-5-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-hydroxy-6-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 989b36fd-7297-41a6-99e5-1e73692b1ba3
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-3-(3,4-dihydroxy-5-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-hydroxy-6-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C(=C4)OC)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C26H32O13/c1-34-16-5-10(3-14(28)19(16)30)23-12-8-37-24(13(12)9-36-23)11-4-15(29)25(17(6-11)35-2)39-26-22(33)21(32)20(31)18(7-27)38-26/h3-6,12-13,18,20-24,26-33H,7-9H2,1-2H3/t12-,13-,18+,20+,21-,22+,23+,24+,26-/m0/s1
• InChI Key: IXJFKGSZQRDHHN-XAWQUCEJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₃
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.18429107 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.07
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5501	55.01%
Caco-2	-	0.8726	87.26%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7266	72.66%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.8567	85.67%
OATP1B3 inhibitior	+	0.9691	96.91%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7214	72.14%
P-glycoprotein inhibitior	-	0.5574	55.74%
P-glycoprotein substrate	-	0.7667	76.67%
CYP3A4 substrate	+	0.5909	59.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7970	79.70%
CYP3A4 inhibition	-	0.8406	84.06%
CYP2C9 inhibition	-	0.8498	84.98%
CYP2C19 inhibition	-	0.7124	71.24%
CYP2D6 inhibition	-	0.8817	88.17%
CYP1A2 inhibition	-	0.8560	85.60%
CYP2C8 inhibition	+	0.6210	62.10%
CYP inhibitory promiscuity	-	0.5107	51.07%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9139	91.39%
Skin irritation	-	0.8431	84.31%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	-	0.6478	64.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.8153	81.53%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8863	88.63%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9551	95.51%
Acute Oral Toxicity (c)	III	0.6689	66.89%
Estrogen receptor binding	+	0.7331	73.31%
Androgen receptor binding	+	0.6487	64.87%
Thyroid receptor binding	+	0.6249	62.49%
Glucocorticoid receptor binding	+	0.5947	59.47%
Aromatase binding	-	0.5252	52.52%
PPAR gamma	+	0.6606	66.06%
Honey bee toxicity	-	0.8341	83.41%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9086	90.86%

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	99.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.57%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.08%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.28%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.47%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.83%	99.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.61%	96.61%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.37%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.49%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.48%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.64%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.05%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.88%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.35%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.48%	95.56%
CHEMBL4208	P20618	Proteasome component C5	81.04%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.95%	95.89%

Plants that contains it

• Eleutherococcus senticosus
• Pedicularis torta
• Symplocos racemosa

Cross-Links

• PubChem: 101701120
• LOTUS: LTS0140556
• wikiData: Q104398881