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Oleoside
- 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)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C16H22O11/c1-2-6-7(3-10(18)19)8(14(23)24)5-25-15(6)27-16-13(22)12(21)11(20)9(4-17)26-16/h2,5,7,9,11-13,15-17,20-22H,3-4H2,1H3,(H,18,19)(H,23,24)/b6-2+/t7-,9+,11+,12-,13+,15-,16-/m0/s1 |
| InChIKey | PNMNSRMFRJNZFD-IPEIANHJSA-N |
| Formula | C16H22O11 |
| HBA | 9 |
| HBD | 6 |
| MW | 390.34 |
| Rotatable Bonds | 6 |
| TPSA | 183.21 |
| LogP | -1.84 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 390.12 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Fraxinus angustifolia | Oleaceae | Plantae | 166594 |
| 2 | Olea europaea | Oleaceae | Plantae | 4146 |
Showing of synonyms
Oleoside
178600-68-5
(4S,5E,6S)-4-(carboxymethyl)-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylic acid
(4S,5E,6S)-4-(carboxymethyl)-5-ethylidene-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-4H-pyran-3-carboxylic acid
2H-Pyran-4-acetic acid, 5-carboxy-3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-, (2S,3E,4S)-
Starbld0000793
CHEMBL4174698
SCHEMBL23521502
PNMNSRMFRJNZFD-IPEIANHJSA-N
DTXSID901319128
HY-N3144
AKOS040762144
DA-56418
FS-10494
CS-0023354
- 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:
101042548
Cas:
178600-68-5
Zinc:
ZINC000096023830
Nmrshiftdb2:
70027850
Chembl:
CHEMBL4174698
No compound-protein relationship available.
SMILES: C1C=COC(C1=C)OC2CCCCO2
Level: 1
Mol. Weight: 390.34 g/mol
SMILES: C=C1CC=COC1
Level: 0
Mol. Weight: 390.34 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 390.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.12
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -6.12
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -6.89
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.1
- Plasma Protein Binding
- 73.1
- 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
- 3.22
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.37
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.28
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.33
- 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
- 5.46
- Rat (Acute)
- 1.86
- Rat (Chronic Oral)
- 3.25
- Fathead Minnow
- 3.15
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 462.43
- Hydration Free Energy
- -10.45
- Log(D) at pH=7.4
- -2.65
- Log(P)
- -1.92
- Log S
- -1.05
- Log(Vapor Pressure)
- -18.48
- Melting Point
- 167.16
- pKa Acid
- 3.69
- pKa Basic
- 4.49
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.8751 |
| Geranyl diphosphate synthase large subunit | Q9SBR3 | Q9SBR3_MENPI | Mentha piperita | 3 | 0.8751 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8122 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8122 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7701 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7701 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7066 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7066 |