(2S,3R,4S,5S,6R)-2-[2-[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-hydroxy-5-(3-hydroxypropyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: c2b279ea-1a27-4cbd-a44d-c9d868c05f7c
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[2-[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-hydroxy-5-(3-hydroxypropyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)C(C(CO)OC2=C(C=C(C=C2OC3C(C(C(C(O3)CO)O)O)O)CCCO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]([C@H](CO)OC2=C(C=C(C=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CCCO)O)O)O
• InChI: InChI=1S/C25H34O13/c1-35-16-9-13(4-5-14(16)29)20(31)18(10-27)36-24-15(30)7-12(3-2-6-26)8-17(24)37-25-23(34)22(33)21(32)19(11-28)38-25/h4-5,7-9,18-23,25-34H,2-3,6,10-11H2,1H3/t18-,19+,20+,21+,22-,23+,25+/m0/s1
• InChI Key: FBQYBPJOZIMVFL-HCENPMPGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₁₃
• Molecular Weight: 542.50 g/mol
• Exact Mass: 542.19994113 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -1.32
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7971	79.71%
Caco-2	-	0.8842	88.42%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6739	67.39%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.8268	82.68%
OATP1B3 inhibitior	+	0.9542	95.42%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5325	53.25%
P-glycoprotein inhibitior	-	0.5177	51.77%
P-glycoprotein substrate	-	0.5295	52.95%
CYP3A4 substrate	+	0.6317	63.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7717	77.17%
CYP3A4 inhibition	-	0.9260	92.60%
CYP2C9 inhibition	-	0.8199	81.99%
CYP2C19 inhibition	-	0.8978	89.78%
CYP2D6 inhibition	-	0.9158	91.58%
CYP1A2 inhibition	-	0.8625	86.25%
CYP2C8 inhibition	+	0.6867	68.67%
CYP inhibitory promiscuity	-	0.8538	85.38%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6816	68.16%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9123	91.23%
Skin irritation	-	0.8133	81.33%
Skin corrosion	-	0.9494	94.94%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8366	83.66%
Micronuclear	-	0.6441	64.41%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8769	87.69%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8602	86.02%
Acute Oral Toxicity (c)	III	0.7900	79.00%
Estrogen receptor binding	+	0.7957	79.57%
Androgen receptor binding	+	0.5238	52.38%
Thyroid receptor binding	-	0.4874	48.74%
Glucocorticoid receptor binding	-	0.5807	58.07%
Aromatase binding	+	0.5780	57.80%
PPAR gamma	+	0.6634	66.34%
Honey bee toxicity	-	0.7904	79.04%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.6894	68.94%

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	99.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.86%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.49%	99.17%
CHEMBL2581	P07339	Cathepsin D	95.40%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.93%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.25%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.15%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.11%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.75%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.21%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.26%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.31%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	85.23%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.54%	86.92%
CHEMBL4208	P20618	Proteasome component C5	82.25%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.95%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.92%	89.00%
CHEMBL2535	P11166	Glucose transporter	81.55%	98.75%
CHEMBL4581	P52732	Kinesin-like protein 1	80.03%	93.18%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.02%	92.62%

Plants that contains it

• Tetracentron sinense

Cross-Links

• PubChem: 163038564
• LOTUS: LTS0028264
• wikiData: Q104992834