10-Hydroxyligstroside

Details

• Internal ID: 48f628fe-eaee-4c48-90b2-b08095e51ff0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5E,6S)-5-(2-hydroxyethylidene)-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): COC(=O)C1=COC(C(=CCO)C1CC(=O)OCCC2=CC=C(C=C2)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H](/C(=C/CO)/[C@@H]1CC(=O)OCCC2=CC=C(C=C2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C25H32O13/c1-34-23(33)17-12-36-24(38-25-22(32)21(31)20(30)18(11-27)37-25)15(6-8-26)16(17)10-19(29)35-9-7-13-2-4-14(28)5-3-13/h2-6,12,16,18,20-22,24-28,30-32H,7-11H2,1H3/b15-6+/t16-,18+,20+,21-,22+,24-,25-/m0/s1
• InChI Key: AHTRGGWSBFOEEG-HFLHEASMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₃
• Molecular Weight: 540.50 g/mol
• Exact Mass: 540.18429107 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.37
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

• 10-Hydroxyligustroside
• AKOS040762759
• 35897-94-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7129	71.29%
Caco-2	-	0.8988	89.88%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8423	84.23%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.7395	73.95%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7393	73.93%
P-glycoprotein inhibitior	-	0.4866	48.66%
P-glycoprotein substrate	+	0.5262	52.62%
CYP3A4 substrate	+	0.6806	68.06%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8680	86.80%
CYP3A4 inhibition	-	0.9304	93.04%
CYP2C9 inhibition	-	0.8577	85.77%
CYP2C19 inhibition	-	0.7491	74.91%
CYP2D6 inhibition	-	0.8903	89.03%
CYP1A2 inhibition	-	0.8160	81.60%
CYP2C8 inhibition	+	0.8193	81.93%
CYP inhibitory promiscuity	-	0.8875	88.75%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6610	66.10%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9253	92.53%
Skin irritation	-	0.8275	82.75%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3930	39.30%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8610	86.10%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6884	68.84%
Acute Oral Toxicity (c)	III	0.6226	62.26%
Estrogen receptor binding	+	0.8305	83.05%
Androgen receptor binding	+	0.6624	66.24%
Thyroid receptor binding	-	0.5321	53.21%
Glucocorticoid receptor binding	+	0.6522	65.22%
Aromatase binding	-	0.4829	48.29%
PPAR gamma	+	0.6643	66.43%
Honey bee toxicity	-	0.7218	72.18%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.8700	87.00%

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	98.06%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.74%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.91%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.33%	95.64%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.73%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.71%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.42%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.96%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.58%	94.73%
CHEMBL3437	Q16853	Amine oxidase, copper containing	85.48%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.75%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.89%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.12%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.04%	96.90%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.71%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.95%	94.62%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.58%	85.00%

Plants that contains it

• Fraxinus angustifolia subsp. oxycarpa
• Fraxinus excelsior
• Fraxinus uhdei
• Jasminum elongatum
• Jasminum multiflorum
• Ligustrum japonicum
• Ligustrum lucidum
• Ligustrum obtusifolium
• Ligustrum vulgare
• Osmanthus fragrans
• Osmanthus heterophyllus

Cross-Links

• PubChem: 14756316
• NPASS: NPC82614
• LOTUS: LTS0144369
• wikiData: Q104394417