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GI-5
- Family: Plantae - Oleaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Secoiridoid Glucoside
| Canonical Smiles | OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H](/C/2=C\C)CC(=O)OCCc2ccc(cc2)OC(=O)C[C@H]2/C(=C\C)/[C@@H](OC=C2C(=O)OC)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C42H54O22/c1-5-21-23(25(37(53)55-3)17-58-39(21)63-41-35(51)33(49)31(47)27(15-43)61-41)13-29(45)57-12-11-19-7-9-20(10-8-19)60-30(46)14-24-22(6-2)40(59-18-26(24)38(54)56-4)64-42-36(52)34(50)32(48)28(16-44)62-42/h5-10,17-18,23-24,27-28,31-36,39-44,47-52H,11-16H2,1-4H3/b21-5+,22-6+/t23-,24-,27+,28+,31+,32+,33-,34-,35+,36+,39-,40-,41-,42-/m0/s1 |
| InChIKey | ALDOLERJIYTYDY-CLEQCBGDSA-N |
| Formula | C42H54O22 |
| HBA | 22 |
| HBD | 8 |
| MW | 910.87 |
| Rotatable Bonds | 16 |
| TPSA | 322.42 |
| LogP | -1.96 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 64 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.57 |
| Exact Mass | 910.31 |
| 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
GI-5
Methyl (4S,5E,6S)-5-ethylidene-4-[2-[2-[4-[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]acetyl]oxyphenyl]ethoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
NCGC00169398-02_C42H54O22_2H-Pyran-4-acetic acid, 3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, 2-[4-[[2-[(2S,3E,4S)-3-ethylidene-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-yl]acetyl]oxy]phenyl]ethyl ester, (2S,3E,4S)-
MEGxp0_000488
ACon0_000905
ACon1_000746
CHEBI:182141
NCGC00169398-01
NCGC00169398-02
BRD-K09019767-001-01-7
- 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: O1CCCCC1OC2OC=CC(C2=C)CC(=O)OCCc3ccc(cc3)OC(=O)CC(C4=C)C=COC4OC5CCCCO5
Level: 4
Mol. Weight: 910.87 g/mol
SMILES: O1CCCCC1OC2OC=CC(C2=C)CC(=O)OCCc3ccc(cc3)OC(=O)CC(C4=C)C=COC4
Level: 3
Mol. Weight: 910.87 g/mol
SMILES: C1OC=CC(C1=C)CC(=O)OCCc2ccc(cc2)OC(=O)CC(C3=C)C=COC3OC4CCCCO4
Level: 3
Mol. Weight: 910.87 g/mol
SMILES: C1OC=CC(C1=C)CC(=O)OCCc2ccc(cc2)OC(=O)CC(C3=C)C=COC3
Level: 2
Mol. Weight: 910.87 g/mol
SMILES: c1ccccc1CCOC(=O)CC(C2=C)C=COC2OC3CCCCO3
Level: 2
Mol. Weight: 910.87 g/mol
SMILES: c1ccccc1OC(=O)CC(C2=C)C=COC2OC3CCCCO3
Level: 2
Mol. Weight: 910.87 g/mol
SMILES: C1OC=CC(C1=C)CC(=O)OCCc2ccccc2
Level: 1
Mol. Weight: 910.87 g/mol
SMILES: C1OC=CC(C1=C)CC(=O)Oc2ccccc2
Level: 1
Mol. Weight: 910.87 g/mol
SMILES: C1C=COC(C1=C)OC2CCCCO2
Level: 1
Mol. Weight: 910.87 g/mol
SMILES: C=C1CC=COC1
Level: 0
Mol. Weight: 910.87 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 910.87 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 910.87 g/mol
Adipocyte differentiation-inhibitory
Antidiabetic
Antiobesity property
Absorption
- Caco-2 (logPapp)
- -6.17
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 1300.060
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 170670.66
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.600
- Plasma Protein Binding
- 66.17
- 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
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 3.990
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Safe
- Bioconcentration Factor
- -3967.770
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.770
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.060
- 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
- -309761227.570
- Rat (Acute)
- 3.080
- Rat (Chronic Oral)
- 6.130
- Fathead Minnow
- 391016.670
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 34833534.630
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- -5.050
- Log(P)
- -0.39
- Log S
- -2.85
- Log(Vapor Pressure)
- -1146948.77
- Melting Point
- 197.19
- pKa Acid
- -8277.26
- pKa Basic
- -43.0
| 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 | 0.8121 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8121 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7782 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7782 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7146 |
| Putative b-glycan phosphorylase | Q21MB1 | Q21MB1_SACD2 | Saccharophagus degradans | 4 | 0.7146 |