(-)-Isolariciresinol 9'-O-glucoside

Details

• Internal ID: b1c9f49e-133d-4e5c-9256-c461cdfa05ae
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1R,2S,3S)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=C2C(C(C(CC2=C1)CO)COC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)O)OC)O
• SMILES (Isomeric): COC1=C(C=C2[C@H]([C@@H]([C@H](CC2=C1)CO)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC(=C(C=C4)O)OC)O
• InChI: InChI=1S/C26H34O11/c1-34-19-6-12(3-4-17(19)29)22-15-8-18(30)20(35-2)7-13(15)5-14(9-27)16(22)11-36-26-25(33)24(32)23(31)21(10-28)37-26/h3-4,6-8,14,16,21-33H,5,9-11H2,1-2H3/t14-,16-,21-,22-,23-,24+,25-,26-/m1/s1
• InChI Key: AHYOMNWKYGMYMB-PBJGOBETSA-N
• Popularity: 3 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): 179.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.16
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• 143236-04-8
• (2R,3R,4S,5S,6R)-2-[[(1R,2S,3S)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• beta-D-Glucopyranoside, [(1R,2S,3S)-1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-6-methoxy-2-naphthalenyl]methyl
• CHEMBL459617
• DTXSID901255152
• AKOS040761895
• (-)-Isolariciresinol 3alpha-O-beta-D-glucopyranoside
• (2S)-3beta-[(beta-D-Glucopyranosyloxy)methyl]-4alpha-(3-methoxy-4-hydroxyphenyl)-6-hydroxy-7-methoxytetralin-2alpha-methanol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5417	54.17%
Caco-2	-	0.8372	83.72%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5963	59.63%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.8670	86.70%
OATP1B3 inhibitior	+	0.9691	96.91%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5642	56.42%
P-glycoprotein inhibitior	-	0.6092	60.92%
P-glycoprotein substrate	-	0.6606	66.06%
CYP3A4 substrate	+	0.6130	61.30%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.7492	74.92%
CYP3A4 inhibition	-	0.8799	87.99%
CYP2C9 inhibition	-	0.8790	87.90%
CYP2C19 inhibition	-	0.7680	76.80%
CYP2D6 inhibition	-	0.9091	90.91%
CYP1A2 inhibition	-	0.7748	77.48%
CYP2C8 inhibition	+	0.6256	62.56%
CYP inhibitory promiscuity	-	0.6057	60.57%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6627	66.27%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9378	93.78%
Skin irritation	-	0.8428	84.28%
Skin corrosion	-	0.9570	95.70%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7635	76.35%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9211	92.11%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8276	82.76%
Acute Oral Toxicity (c)	III	0.6609	66.09%
Estrogen receptor binding	+	0.8035	80.35%
Androgen receptor binding	+	0.5937	59.37%
Thyroid receptor binding	+	0.5754	57.54%
Glucocorticoid receptor binding	-	0.4670	46.70%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5339	53.39%
Honey bee toxicity	-	0.8189	81.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8329	83.29%

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	99.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.96%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.43%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.24%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.91%	89.62%
CHEMBL2581	P07339	Cathepsin D	91.56%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.20%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.42%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.93%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.72%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.69%	94.00%
CHEMBL4208	P20618	Proteasome component C5	84.67%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	84.64%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.04%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.93%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	82.07%	88.48%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.11%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.86%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.49%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.35%	96.00%

Plants that contains it

• Annona squamosa
• Bauhinia tarapotensis
• Breynia androgyna
• Salvia officinalis
• Spiraea canescens
• Tinospora sinensis

Cross-Links

• PubChem: 44560003
• NPASS: NPC272619
• ChEMBL: CHEMBL459617
• LOTUS: LTS0189148
• wikiData: Q104888461