Oleuropein aglycone

Details

• Internal ID: a71ce973-76b4-4a72-aa3f-44883607bf20
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: methyl (4S,5E,6R)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-hydroxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C(C(=COC1O)C(=O)OC)CC(=O)OCCC2=CC(=C(C=C2)O)O
• SMILES (Isomeric): C/C=C/1\[C@@H](C(=CO[C@H]1O)C(=O)OC)CC(=O)OCCC2=CC(=C(C=C2)O)O
• InChI: InChI=1S/C19H22O8/c1-3-12-13(14(18(23)25-2)10-27-19(12)24)9-17(22)26-7-6-11-4-5-15(20)16(21)8-11/h3-5,8,10,13,19-21,24H,6-7,9H2,1-2H3/b12-3+/t13-,19+/m0/s1
• InChI Key: BIWKXNFEOZXNLX-BBHIFXBUSA-N
• Popularity: 47 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₈
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.13146766 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.54
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 31773-95-2
• Oleuropein aglycon
• CHEBI:139162
• DTXSID70953711
• methyl (2R,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-hydroxy-3,4-dihydro-2H-pyran-5-carboxylate
• methyl (4s,5e,6r)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-hydroxy-4h-pyran-3-carboxylate
• JVQ6P3R5XV
• methyl (2R,3E,4S)-4-(2-(2-(3,4-dihydroxyphenyl)ethoxy)-2-oxoethyl)-3-ethylidene-2-hydroxy-3,4-dihydro-2H-pyran-5-carboxylate
• methyl (4S,5E,6R)-4-(2-(2-(3,4-dihydroxyphenyl)ethoxy)-2-oxoethyl)-5-ethylidene-6-hydroxy-4H-pyran-3-carboxylate
• RefChem:928166
• DTXCID801770913
• Oleuropeinaglycon
• Oleuropeine aglycone
• Oleoeuropein aglycone
• 2H-PYRAN-4-ACETIC ACID,3-ETHYLIDENE-3,4-DIHYDRO-2-HYDROXY-5-(METHOXYCARBONYL)-,2-(3,4-DIHYDROXYPHENYL)ETHYL ESTER, (2R,3E,4S)-
• Oleuropein aglycone - 80%
• 2H-Pyran-4-acetic acid, 3-ethylidene-3,4-dihydro-2-hydroxy-5-(methoxycarbonyl)-, 2-(3,4-dihydroxyphenyl) ethyl ester, (2R-(2alpha,3E,4beta))-
• Methyl (2R,4S,E)-4-(2-(3,4-dihydroxyphenethoxy)-2-oxoethyl)-3-ethylidene-2-hydroxy-3,4-dihydro-2H-pyran-5-carboxylate
• Oleuropein-aglycone
• Oleuropein_aglycone
• CHEMBL4471855
• SCHEMBL12642033
• SCHEMBL29454793
• BIWKXNFEOZXNLX-BBHIFXBUSA-N
• BO300163
• XO180873
• HY-135115
• CS-0109412
• H61308
• (2R,3E,4S)-3-Ethylidene-3,4-dihydro-2-hydroxy-5-(methoxycarbonyl)-2H-pyran-4-acetic acid
• methyl (4S,5E,6R)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxo-ethyl]-5-ethylidene-6-hydroxy-4H-pyran-3-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6311	63.11%
Caco-2	-	0.7006	70.06%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.9246	92.46%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.7793	77.93%
OATP1B3 inhibitior	+	0.9358	93.58%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.7335	73.35%
P-glycoprotein inhibitior	-	0.5144	51.44%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6297	62.97%
CYP2C9 substrate	+	0.6060	60.60%
CYP2D6 substrate	-	0.8695	86.95%
CYP3A4 inhibition	-	0.6970	69.70%
CYP2C9 inhibition	-	0.6532	65.32%
CYP2C19 inhibition	+	0.6839	68.39%
CYP2D6 inhibition	-	0.8156	81.56%
CYP1A2 inhibition	+	0.6848	68.48%
CYP2C8 inhibition	+	0.7640	76.40%
CYP inhibitory promiscuity	-	0.6959	69.59%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7709	77.09%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.8676	86.76%
Skin irritation	-	0.8272	82.72%
Skin corrosion	-	0.9661	96.61%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4526	45.26%
Micronuclear	-	0.7041	70.41%
Hepatotoxicity	-	0.7966	79.66%
skin sensitisation	-	0.7945	79.45%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6715	67.15%
Acute Oral Toxicity (c)	III	0.5292	52.92%
Estrogen receptor binding	+	0.7790	77.90%
Androgen receptor binding	+	0.7468	74.68%
Thyroid receptor binding	+	0.5658	56.58%
Glucocorticoid receptor binding	+	0.7467	74.67%
Aromatase binding	-	0.5488	54.88%
PPAR gamma	+	0.6197	61.97%
Honey bee toxicity	-	0.7945	79.45%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9745	97.45%

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	97.36%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.69%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.45%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	91.03%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.58%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	89.81%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.97%	98.95%
CHEMBL4208	P20618	Proteasome component C5	84.59%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.33%	90.71%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.81%	80.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.46%	95.89%
CHEMBL3194	P02766	Transthyretin	81.17%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	81.12%	91.19%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.80%	96.90%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.14%	92.62%

Plants that contains it

• Olea europaea

Cross-Links

• PubChem: 56842347
• LOTUS: LTS0053795
• wikiData: Q74411133