10-Hydroxyoleuropein

Details

• Internal ID: 41237873-b4c9-4aa6-8320-d6623efc8e66
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-(2-hydroxyethylidene)-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)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)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C25H32O14/c1-35-23(34)15-11-37-24(39-25-22(33)21(32)20(31)18(10-27)38-25)13(4-6-26)14(15)9-19(30)36-7-5-12-2-3-16(28)17(29)8-12/h2-4,8,11,14,18,20-22,24-29,31-33H,5-7,9-10H2,1H3/b13-4+/t14-,18+,20+,21-,22+,24-,25-/m0/s1
• InChI Key: JCWFMPVGIIRRRG-AXPMACIOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₂O₁₄
• Molecular Weight: 556.50 g/mol
• Exact Mass: 556.17920569 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.66
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

• 84638-44-8
• methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-(2-hydroxyethylidene)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• 2H-Pyran-4-acetic acid, 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-(2-hydroxyethylidene)-5-(methoxycarbonyl)-, 2-(3,4-dihydroxyphenyl)ethyl ester, (2S,3E,4S)-
• C25H32O14
• AKOS040734250
• C25-H32-O14

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6666	66.66%
Caco-2	-	0.9096	90.96%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8134	81.34%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.7772	77.72%
OATP1B3 inhibitior	+	0.9482	94.82%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6277	62.77%
P-glycoprotein inhibitior	-	0.5235	52.35%
P-glycoprotein substrate	-	0.5123	51.23%
CYP3A4 substrate	+	0.6769	67.69%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8663	86.63%
CYP3A4 inhibition	-	0.9122	91.22%
CYP2C9 inhibition	-	0.8076	80.76%
CYP2C19 inhibition	-	0.6984	69.84%
CYP2D6 inhibition	-	0.8819	88.19%
CYP1A2 inhibition	-	0.7196	71.96%
CYP2C8 inhibition	+	0.7837	78.37%
CYP inhibitory promiscuity	-	0.8685	86.85%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7063	70.63%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9215	92.15%
Skin irritation	-	0.8302	83.02%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7169	71.69%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8302	83.02%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7773	77.73%
Acute Oral Toxicity (c)	III	0.6290	62.90%
Estrogen receptor binding	+	0.8193	81.93%
Androgen receptor binding	+	0.6824	68.24%
Thyroid receptor binding	-	0.5249	52.49%
Glucocorticoid receptor binding	+	0.6450	64.50%
Aromatase binding	+	0.5232	52.32%
PPAR gamma	+	0.6870	68.70%
Honey bee toxicity	-	0.7221	72.21%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8978	89.78%

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	98.85%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.52%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.50%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.74%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	92.62%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.54%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.03%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.84%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.37%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.09%	95.64%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.50%	96.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	85.26%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.63%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.55%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.43%	95.83%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.11%	80.78%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.81%	96.61%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.22%	94.33%
CHEMBL3194	P02766	Transthyretin	80.20%	90.71%

Plants that contains it

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

Cross-Links

• PubChem: 6440747
• NPASS: NPC159337
• LOTUS: LTS0108909
• wikiData: Q104397193