(2S,3R,4S,5S,6R)-2-[4-[[(3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 18d92e0e-069c-4706-a2a2-07f503f03810
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[[(3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)O)OC)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@@H]2CO[C@H]([C@@H]2CO)C3=CC(=C(C=C3)O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C26H34O11/c1-33-19-9-14(4-5-17(19)29)25-16(10-27)15(12-35-25)7-13-3-6-18(20(8-13)34-2)36-26-24(32)23(31)22(30)21(11-28)37-26/h3-6,8-9,15-16,21-32H,7,10-12H2,1-2H3/t15-,16-,21-,22-,23+,24-,25+,26-/m1/s1
• InChI Key: GAYKAIAESJROGN-DTIHIKGDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₄O₁₁
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.21011190 g/mol
• Topological Polar Surface Area (TPSA): 168.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7025	70.25%
Caco-2	-	0.8477	84.77%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8022	80.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8540	85.40%
OATP1B3 inhibitior	+	0.9605	96.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5442	54.42%
P-glycoprotein inhibitior	-	0.4600	46.00%
P-glycoprotein substrate	-	0.6858	68.58%
CYP3A4 substrate	+	0.6439	64.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7860	78.60%
CYP3A4 inhibition	-	0.7667	76.67%
CYP2C9 inhibition	-	0.8245	82.45%
CYP2C19 inhibition	-	0.7386	73.86%
CYP2D6 inhibition	-	0.8963	89.63%
CYP1A2 inhibition	-	0.8578	85.78%
CYP2C8 inhibition	+	0.7669	76.69%
CYP inhibitory promiscuity	+	0.5593	55.93%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6301	63.01%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9309	93.09%
Skin irritation	-	0.8573	85.73%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8288	82.88%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8831	88.31%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.9260	92.60%
Acute Oral Toxicity (c)	III	0.7137	71.37%
Estrogen receptor binding	+	0.7006	70.06%
Androgen receptor binding	+	0.5603	56.03%
Thyroid receptor binding	+	0.5851	58.51%
Glucocorticoid receptor binding	-	0.4676	46.76%
Aromatase binding	-	0.5453	54.53%
PPAR gamma	+	0.5747	57.47%
Honey bee toxicity	-	0.7844	78.44%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8946	89.46%

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	99.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.61%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.32%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.98%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.08%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.59%	97.09%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	91.55%	85.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.30%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.60%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.98%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.89%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.35%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.33%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.91%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.42%	86.92%
CHEMBL4208	P20618	Proteasome component C5	83.99%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.40%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.95%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.75%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	81.65%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.86%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.57%	97.33%
CHEMBL1951	P21397	Monoamine oxidase A	80.43%	91.49%

Plants that contains it

• Balanophora laxiflora
• Clematis hexapetala
• Daphne giraldii
• Marrubium velutinum

Cross-Links

• PubChem: 102322385
• LOTUS: LTS0198767
• wikiData: Q105005709