Select a section from the left sidebar
Oleoside 11-methyl ester
- Family: Plantae - Oleaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Secoiridoid Glucoside
| Canonical Smiles | C/C=C\1/[C@@H](OC=C([C@H]1CC(=O)O)C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6,8,10,12-14,16-18,21-23H,4-5H2,1-2H3,(H,19,20)/b7-3+/t8-,10+,12+,13-,14+,16-,17-/m0/s1 |
| InChIKey | XSCVKBFEPYGZSL-JYVCFIOWSA-N |
| Formula | C17H24O11 |
| HBA | 10 |
| HBD | 5 |
| MW | 404.37 |
| Rotatable Bonds | 6 |
| TPSA | 172.21 |
| LogP | -1.75 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 404.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Fraxinus excelsior | Oleaceae | Plantae | 38873 |
| 2 | Fraxinus excelsior | Oleaceae | Plantae | 38873 |
| 3 | Fraxinus angustifolia | Oleaceae | Plantae | 166594 |
| 4 | Olea europaea | Oleaceae | Plantae | 4146 |
Showing of synonyms
Oleoside 11-methyl ester
60539-23-3
11-Methyloleoside
2-[(2S,3E,4S)-3-Ethylidene-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetic acid
CHEBI:168822
((2S,3E,4S)-3-ethylidene-2-(beta-D-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-4-yl)acetic acid
[(2S,3E,4S)-3-ethylidene-2-(beta-D-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2H-pyran-4-yl]acetic acid
2-((2S,3E,4S)-3-ethylidene-5-methoxycarbonyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-4H-pyran-4-yl)acetic acid
2-(3-Ethylidene-5-(methoxycarbonyl)-2-((3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)-3,4-dihydro-2H-pyran-4-yl)acetate
2-[3-Ethylidene-5-(methoxycarbonyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetate
2-((2S,3Z,4S)-3-ethylidene-5-methoxycarbonyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-4H-pyran-4-yl)acetic acid
2-[(2S,3Z,4S)-3-ethylidene-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetic acid
Methyloleoside
ELENOLIC ACID 2-O-GLUCOSIDE
2-((2S,4S,E)-3-Ethylidene-5-(methoxycarbonyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-4-yl)acetic acid
2H-Pyran-4-acetic acid, 3-ethylidene-2-(ss-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2S,3E,4S)-
2H-Pyran-4-acetic acid, 3-ethylidene-2-(ss-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, [2S-(2a,3E,4ss)]-
CHEMBL4159745
SCHEMBL23494908
DTXSID501313328
HY-N8882
Elenolic acid glucoside, HPLC Grade
MFCD09752800
AKOS040762057
FS-7441
AC-34501
DA-65406
CS-0149294
E87147
- Ibarra A, Bai N, et al. (2011). Fraxinus excelsior seed extract FraxiPureTM limits weight gains and hyperglycemia in high-fat diet-induced obese mice. Phytomedicine,2011,18(6),479-485. [View]
- Bai N, He K, et al. (2010). Iridoids from Fraxinus excelsior with adipocyte differentiation-inhibitory and PPARalpha activation activity. Journal of Natural Products,2010,73(1),2-6. [View] [PubMed]
- Ben Mansour A, Porter EA, et al. (2015). Phenolic profile characterization of Chemlali olive stones by liquid chromatography-ion trap mass spectrometry. Journal of Agricultural and Food Chemistry,2015,63(7),1990-1995. [View]
- García-Villalba R, Tomás-Barberán FA, et al. (2015). Targeted and untargeted metabolomics to explore the bioavailability of the secoiridoids from a seed/fruit extract (Fraxinus angustifolia Vahl) in human healthy volunteers: a preliminary study. Molecules,2015,20(12),22202-22219. [View] [PubMed]
Pubchem:
10692563
Cas:
60539-23-3
Zinc:
ZINC000039180894
Chebi:
168822
Nmrshiftdb2:
60062930
Metabolights:
MTBLC168822
Chembl:
CHEMBL4159745
No compound-protein relationship available.
SMILES: C1C=COC(C1=C)OC2CCCCO2
Level: 1
Mol. Weight: 404.37 g/mol
SMILES: C=C1CC=COC1
Level: 0
Mol. Weight: 404.37 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 404.37 g/mol
Adipocyte differentiation-inhibitory
Antiobesity property
Absorption
- Caco-2 (logPapp)
- -5.98
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.3
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -4.04
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.51
- Plasma Protein Binding
- 63.41
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.29
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -2.07
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.17
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.67
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -2.25
- Rat (Acute)
- 1.83
- Rat (Chronic Oral)
- 3.12
- Fathead Minnow
- 3.68
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 449.33
- Hydration Free Energy
- -9.26
- Log(D) at pH=7.4
- -0.87
- Log(P)
- -1.3
- Log S
- -0.92
- Log(Vapor Pressure)
- -14.78
- Melting Point
- 162.83
- pKa Acid
- 2.85
- pKa Basic
- 3.94
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8114 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8114 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7462 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7462 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7174 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7174 |