2-Methoxy-4-[(1S,2R)-1,3-dihydroxy-2-[2-methoxy-4-[3-(beta-D-glucopyranosyloxy)propyl]phenoxy]propyl]phenol

Details

• Internal ID: 35e34166-4396-41b2-9805-88ec24f719a0
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[3-[4-[(1S,2R)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)CCCOC2C(C(C(C(O2)CO)O)O)O)OC(CO)C(C3=CC(=C(C=C3)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CCCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O[C@H](CO)[C@H](C3=CC(=C(C=C3)O)OC)O
• InChI: InChI=1S/C26H36O12/c1-34-18-11-15(6-7-16(18)29)22(30)20(12-27)37-17-8-5-14(10-19(17)35-2)4-3-9-36-26-25(33)24(32)23(31)21(13-28)38-26/h5-8,10-11,20-33H,3-4,9,12-13H2,1-2H3/t20-,21-,22+,23-,24+,25-,26-/m1/s1
• InChI Key: NFUHNVZGHNEYRG-GKRKWVKGSA-N
• Popularity: 0 references 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

• 2-Methoxy-4-[(1S,2R)-1,3-dihydroxy-2-[2-methoxy-4-[3-(beta-D-glucopyranosyloxy)propyl]phenoxy]propyl]phenol
• 3-(4-{[(1S,2R)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)propyl b-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8359	83.59%
Caco-2	-	0.8600	86.00%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7374	73.74%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8312	83.12%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5608	56.08%
P-glycoprotein inhibitior	-	0.4426	44.26%
P-glycoprotein substrate	+	0.5599	55.99%
CYP3A4 substrate	+	0.6470	64.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7717	77.17%
CYP3A4 inhibition	-	0.9151	91.51%
CYP2C9 inhibition	-	0.7050	70.50%
CYP2C19 inhibition	-	0.8331	83.31%
CYP2D6 inhibition	-	0.9173	91.73%
CYP1A2 inhibition	-	0.8228	82.28%
CYP2C8 inhibition	+	0.7357	73.57%
CYP inhibitory promiscuity	-	0.7357	73.57%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7145	71.45%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9370	93.70%
Skin irritation	-	0.8489	84.89%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7193	71.93%
Micronuclear	-	0.6541	65.41%
Hepatotoxicity	-	0.8321	83.21%
skin sensitisation	-	0.8899	88.99%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.9296	92.96%
Acute Oral Toxicity (c)	III	0.7950	79.50%
Estrogen receptor binding	+	0.7671	76.71%
Androgen receptor binding	+	0.5272	52.72%
Thyroid receptor binding	+	0.5772	57.72%
Glucocorticoid receptor binding	-	0.4634	46.34%
Aromatase binding	-	0.5253	52.53%
PPAR gamma	+	0.5543	55.43%
Honey bee toxicity	-	0.8117	81.17%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.5412	54.12%

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	99.30%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.91%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.90%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.73%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.76%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.71%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.36%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.05%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.21%	95.89%
CHEMBL1255126	O15151	Protein Mdm4	89.15%	90.20%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.37%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.64%	89.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.34%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.81%	90.71%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.94%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.66%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	81.32%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.24%	99.15%

Plants that contains it

• Adenopeltis serrata
• Bituminaria bituminosa
• Centaurea seridis
• Chrozophora tinctoria
• Cneorum pulverulentum
• Dalbergia stipulacea
• Delphinium ajacis
• Elaeagnus commutata
• Eucalyptus flocktoniae
• Flindersia brayleyana
• Heracleum sphondylium
• Jungermannia obovata
• Kummerowia striata
• Lonicera gracilipes
• Mascarenhasia arborescens
• Meconopsis napaulensis
• Merremia umbellata
• Millettia conraui
• Palafoxia rosea
• Pedicularis condensata
• Perityle vaseyi
• Phoebe formosana
• Piloselloides hirsuta
• Plectranthus garckeanus
• Porella swartziana
• Quercus mongolica
• Rheum webbianum
• Salacia chinensis
• Salvia coulteri
• Satureja cuneifolia
• Senecio flavus
• Sida cordifolia
• Solanum sisymbriifolium
• Thymbra spicata
• Turraeanthus mannii

Cross-Links

• PubChem: 21672401
• NPASS: NPC176679
• LOTUS: LTS0236826
• wikiData: Q82873461