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Excelside A
- Family: Plantae - Oleaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Secoiridoid Glucoside
| Canonical Smiles | COC(=O)C[C@H]1/C(=C\C)/C(OC=C1C(=O)OC)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C24H36O16/c1-4-9-10(5-14(26)34-2)11(21(33)35-3)7-36-22(9)40-24-20(32)18(30)16(28)13(39-24)8-37-23-19(31)17(29)15(27)12(6-25)38-23/h4,7,10,12-13,15-20,22-25,27-32H,5-6,8H2,1-3H3/b9-4+/t10-,12+,13+,15+,16+,17-,18-,19+,20+,22?,23+,24-/m0/s1 |
| InChIKey | KIYJRYWOZVDCRC-GLYOJDOWSA-N |
| Formula | C24H36O16 |
| HBA | 16 |
| HBD | 7 |
| MW | 580.54 |
| Rotatable Bonds | 9 |
| TPSA | 240.36 |
| LogP | -3.83 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 580.2 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Fraxinus excelsior | Oleaceae | Plantae | 38873 |
| 2 | Fraxinus excelsior | Oleaceae | Plantae | 38873 |
Showing of synonyms
Excelside A
Methyl (4S,5E)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4H-pyran-3-carboxylate
Methyl (2S,4S)-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)methyl)oxan-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carboxylic acid
Methyl (2S,4S)-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid
Methyl (4S,5E)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethyl)oxan-2-yl)oxy-4H-pyran-3-carboxylate
(2S,4S,3E)-Methyl-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate
1149762-75-3
CHEMBL1086876
CHEBI:197410
- 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]
No compound-protein relationship available.
SMILES: C1C=COC(C1=C)OC(O2)CCCC2COC3CCCCO3
Level: 2
Mol. Weight: 580.54 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 580.54 g/mol
SMILES: C1C=COC(C1=C)OC2CCCCO2
Level: 1
Mol. Weight: 580.54 g/mol
SMILES: C=C1CC=COC1
Level: 0
Mol. Weight: 580.54 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 580.54 g/mol
Adipocyte differentiation-inhibitory
Antiobesity property
Absorption
- Caco-2 (logPapp)
- -6.14
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.110
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 0.52
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.780
- Plasma Protein Binding
- 53.47
- 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
- 5.130
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -4.660
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.150
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.950
- Micronucleos
- Safe
- 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
- -2394.060
- Rat (Acute)
- 2.510
- Rat (Chronic Oral)
- 4.190
- Fathead Minnow
- 3.600
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 518.290
- Hydration Free Energy
- -3.100
- Log(D) at pH=7.4
- -0.380
- Log(P)
- -2.13
- Log S
- -1.13
- Log(Vapor Pressure)
- -14.71
- Melting Point
- 159.0
- pKa Acid
- 3.59
- pKa Basic
- 2.17
| 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 | 0.8174 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8174 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7705 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7705 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 4 | 0.7435 |
| Periplasmic pH-dependent serine endoprotease DegQ | P39099 | DEGQ_ECOLI | Escherichia coli | 4 | 0.7435 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7138 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7138 |