Ligustroside

Details

• Internal ID: 292469ed-a62a-48cd-9e81-ea79079a7306
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5E,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC=C(C=C3)O
• SMILES (Isomeric): C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OCCC3=CC=C(C=C3)O
• InChI: InChI=1S/C25H32O12/c1-3-15-16(10-19(28)34-9-8-13-4-6-14(27)7-5-13)17(23(32)33-2)12-35-24(15)37-25-22(31)21(30)20(29)18(11-26)36-25/h3-7,12,16,18,20-22,24-27,29-31H,8-11H2,1-2H3/b15-3+/t16-,18+,20+,21-,22+,24-,25-/m0/s1
• InChI Key: GMQXOLRKJQWPNB-MVVLSVRYSA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₂
• Molecular Weight: 524.50 g/mol
• Exact Mass: 524.18937645 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.34
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

• ligstroside
• 35897-92-8
• Ligusroside
• UNII-83S9SA69C5
• 83S9SA69C5
• (-)-ligstroside
• MEGxp0_000487
• CHEMBL1086877
• ACon1_000577
• CHEBI:149585
• DTXSID701318124
• HY-N3383
• methyl (4S,5E,6S)-5-ethylidene-4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• AKOS040760521
• NCGC00168945-01
• MS-29709
• CS-0024058
• BRD-K49137267-001-01-4
• Q27269447
• (2S)-2beta-(beta-D-Glucopyranosyloxy)-3-ethylidene-4alpha-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-3,4-dihydro-2H-pyran-5-carboxylic acid methyl ester
• 2H-PYRAN-4-ACETIC ACID, 3-ETHYLIDENE-2-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,4-DIHYDRO-5-(METHOXYCARBONYL)-, 2-(4-HYDROXYPHENYL)ETHYL ESTER, (2S,3E,4S)-
• methyl (2S,3E,4S)-3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7350	73.50%
Caco-2	-	0.8752	87.52%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8408	84.08%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.7002	70.02%
OATP1B3 inhibitior	+	0.9266	92.66%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7797	77.97%
P-glycoprotein inhibitior	-	0.4891	48.91%
P-glycoprotein substrate	+	0.5517	55.17%
CYP3A4 substrate	+	0.6744	67.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8777	87.77%
CYP3A4 inhibition	-	0.8371	83.71%
CYP2C9 inhibition	-	0.8551	85.51%
CYP2C19 inhibition	-	0.7617	76.17%
CYP2D6 inhibition	-	0.8916	89.16%
CYP1A2 inhibition	-	0.8138	81.38%
CYP2C8 inhibition	+	0.8201	82.01%
CYP inhibitory promiscuity	-	0.8840	88.40%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6906	69.06%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9370	93.70%
Skin irritation	-	0.8177	81.77%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4118	41.18%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8564	85.64%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6337	63.37%
Acute Oral Toxicity (c)	III	0.6267	62.67%
Estrogen receptor binding	+	0.8187	81.87%
Androgen receptor binding	+	0.6805	68.05%
Thyroid receptor binding	-	0.5086	50.86%
Glucocorticoid receptor binding	+	0.7585	75.85%
Aromatase binding	-	0.5667	56.67%
PPAR gamma	+	0.6776	67.76%
Honey bee toxicity	-	0.7087	70.87%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9027	90.27%

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	97.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.97%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.91%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.17%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.13%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.79%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.59%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.80%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.66%	95.64%
CHEMBL3437	Q16853	Amine oxidase, copper containing	86.15%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.33%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.23%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	82.52%	97.79%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.25%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.25%	94.33%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.58%	96.90%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.17%	96.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.58%	85.00%

Plants that contains it

• Fraxinus americana
• Fraxinus angustifolia
• Fraxinus angustifolia subsp. oxycarpa
• Fraxinus chinensis
• Fraxinus chinensis subsp. chinensis
• Fraxinus chinensis subsp. rhynchophylla
• Fraxinus excelsior
• Fraxinus griffithii
• Fraxinus insularis
• Fraxinus ornus
• Fraxinus stylosa
• Fraxinus uhdei
• Jasminum grandiflorum
• Jasminum polyanthum
• Ligustrum japonicum
• Ligustrum lucidum
• Ligustrum vulgare
• Olea europaea
• Osmanthus heterophyllus
• Phillyrea latifolia
• Picconia excelsa
• Syringa pubescens subsp. patula
• Syringa reticulata
• Syringa reticulata subsp. amurensis
• Syringa vulgaris
• Tetradium ruticarpum

Cross-Links

• PubChem: 14136859
• NPASS: NPC169398
• LOTUS: LTS0041796
• wikiData: Q27269447