(2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol

Details

• Internal ID: 379432ad-9720-4cd3-a983-99469f7eac67
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C(C(CC3=CC(=C(C(=C23)OC)O)OC)CO)COC4C(C(C(CO4)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)[C@@H]2[C@H]([C@@H](CC3=CC(=C(C(=C23)OC)O)OC)CO)CO[C@H]4[C@@H]([C@H]([C@@H](CO4)O)O)O
• InChI: InChI=1S/C27H36O12/c1-34-17-7-13(8-18(35-2)23(17)31)20-15(10-38-27-25(33)22(30)16(29)11-39-27)14(9-28)5-12-6-19(36-3)24(32)26(37-4)21(12)20/h6-8,14-16,20,22,25,27-33H,5,9-11H2,1-4H3/t14-,15-,16+,20+,22-,25+,27+/m0/s1
• InChI Key: GWDZRGQRNHELQM-VEKSOEEBSA-N
• Popularity: 296 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₂
• Molecular Weight: 552.60 g/mol
• Exact Mass: 552.22067658 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.50
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 9

Synonyms

• 34425-25-7
• (2R,3R,4S,5R)-2-[[(1S,2R,3R)-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]methoxy]oxane-3,4,5-triol
• CHEMBL583884
• DTXSID001318597
• HY-N3348
• BDBM50378458
• AKOS032962464
• FS-9782
• CID 14521039
• CS-0023957
• Lyoniresinol, -D-xyloside ; -D-Xylopyranoside, [1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-6,8-dimethoxy-2-naphthalenyl]methyl, [1S-(1,2,3)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5620	56.20%
Caco-2	-	0.8042	80.42%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5778	57.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8456	84.56%
OATP1B3 inhibitior	+	0.9564	95.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6406	64.06%
P-glycoprotein inhibitior	-	0.5356	53.56%
P-glycoprotein substrate	-	0.5069	50.69%
CYP3A4 substrate	+	0.6241	62.41%
CYP2C9 substrate	-	0.8002	80.02%
CYP2D6 substrate	-	0.7492	74.92%
CYP3A4 inhibition	-	0.9278	92.78%
CYP2C9 inhibition	-	0.9314	93.14%
CYP2C19 inhibition	-	0.8547	85.47%
CYP2D6 inhibition	-	0.9078	90.78%
CYP1A2 inhibition	-	0.8014	80.14%
CYP2C8 inhibition	+	0.5778	57.78%
CYP inhibitory promiscuity	-	0.8509	85.09%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6996	69.96%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9273	92.73%
Skin irritation	-	0.8432	84.32%
Skin corrosion	-	0.9603	96.03%
Ames mutagenesis	-	0.5486	54.86%
Human Ether-a-go-go-Related Gene inhibition	+	0.6641	66.41%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	-	0.7320	73.20%
skin sensitisation	-	0.9170	91.70%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9602	96.02%
Acute Oral Toxicity (c)	III	0.6502	65.02%
Estrogen receptor binding	+	0.8419	84.19%
Androgen receptor binding	+	0.6875	68.75%
Thyroid receptor binding	+	0.6099	60.99%
Glucocorticoid receptor binding	+	0.6863	68.63%
Aromatase binding	+	0.6042	60.42%
PPAR gamma	+	0.5996	59.96%
Honey bee toxicity	-	0.8018	80.18%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.8571	85.71%

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	99.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.38%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.89%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.97%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.60%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.94%	89.62%
CHEMBL2581	P07339	Cathepsin D	88.49%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.76%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.93%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.81%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.57%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.76%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.44%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.28%	96.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.72%	94.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.72%	95.89%
CHEMBL2535	P11166	Glucose transporter	80.32%	98.75%

Plants that contains it

• Ampelopsis glandulosa var. brevipedunculata
• Betula papyrifera
• Betula pendula
• Elliottia paniculata
• Epimedium diphyllum
• Ficus glumosa
• Laurus nobilis
• Litsea glutinosa
• Lyonia ovalifolia
• Machilus thunbergii
• Prunus padus
• Quercus petraea
• Saraca asoca
• Ulmus davidiana
• Vaccinium myrtillus
• Viburnum dilatatum

Cross-Links

• PubChem: 14521039
• LOTUS: LTS0201451
• wikiData: Q104396245