(2R,3R,4S,5S,6R)-2-[(1S,2R)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 48a021dc-7620-45c7-bb70-d897a9262704
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(1S,2R)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)CCCO)OC(CO)C(C2=CC(=C(C=C2)O)OC)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CCCO)O[C@H](CO)[C@H](C2=CC(=C(C=C2)O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C26H36O12/c1-34-18-11-15(6-7-16(18)30)25(38-26-24(33)23(32)22(31)20(12-28)37-26)21(13-29)36-17-8-5-14(4-3-9-27)10-19(17)35-2/h5-8,10-11,20-33H,3-4,9,12-13H2,1-2H3/t20-,21-,22-,23+,24-,25+,26+/m1/s1
• InChI Key: HZYWTYSKPVTFNA-MHBFLCIISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₆O₁₂
• Molecular Weight: 540.60 g/mol
• Exact Mass: 540.22067658 g/mol
• Topological Polar Surface Area (TPSA): 188.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.37
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7908	79.08%
Caco-2	-	0.8438	84.38%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6748	67.48%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.8228	82.28%
OATP1B3 inhibitior	+	0.9530	95.30%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5872	58.72%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5875	58.75%
CYP3A4 substrate	+	0.6422	64.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7717	77.17%
CYP3A4 inhibition	-	0.9196	91.96%
CYP2C9 inhibition	-	0.8320	83.20%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9132	91.32%
CYP1A2 inhibition	-	0.8452	84.52%
CYP2C8 inhibition	+	0.6901	69.01%
CYP inhibitory promiscuity	-	0.8645	86.45%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7258	72.58%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9404	94.04%
Skin irritation	-	0.8304	83.04%
Skin corrosion	-	0.9518	95.18%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8265	82.65%
Micronuclear	-	0.6541	65.41%
Hepatotoxicity	-	0.7696	76.96%
skin sensitisation	-	0.8811	88.11%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.9029	90.29%
Acute Oral Toxicity (c)	III	0.8103	81.03%
Estrogen receptor binding	+	0.7814	78.14%
Androgen receptor binding	+	0.5721	57.21%
Thyroid receptor binding	+	0.5707	57.07%
Glucocorticoid receptor binding	+	0.5979	59.79%
Aromatase binding	-	0.4829	48.29%
PPAR gamma	-	0.4935	49.35%
Honey bee toxicity	-	0.7874	78.74%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7249	72.49%
Fish aquatic toxicity	-	0.6355	63.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.21%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.05%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.00%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.88%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.55%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.96%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.07%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.05%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.08%	89.62%
CHEMBL1255126	O15151	Protein Mdm4	85.71%	90.20%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.54%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.97%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.70%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.38%	85.14%
CHEMBL2535	P11166	Glucose transporter	83.14%	98.75%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.82%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.59%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.56%	90.71%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.73%	82.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.13%	97.36%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.64%	100.00%

Plants that contains it

• Lonicera gracilipes

Cross-Links

• PubChem: 10697712
• LOTUS: LTS0180261
• wikiData: Q105035956