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9alpha-acetyloxy-6beta-isobutoyloxy-1alpha,4alpha-epoxy-eudesm-11(13)-en-5beta,7alpha,8alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CC(=O)O[C@@H]1[C@@H]2OC(=O)C(=C)[C@@H]2[C@H]([C@@H]2[C@]1(C)[C@@H]1CC[C@]2(O1)C)OC(=O)C(C)C |
|---|---|
| InChI | InChI=1S/C21H28O7/c1-9(2)18(23)26-14-13-10(3)19(24)27-15(13)17(25-11(4)22)21(6)12-7-8-20(5,28-12)16(14)21/h9,12-17H,3,7-8H2,1-2,4-6H3/t12-,13+,14+,15+,16-,17+,20+,21-/m0/s1 |
| InChIKey | YBNREBQLPMUAKX-QTABAYSHSA-N |
| Formula | C21H28O7 |
| HBA | 7 |
| HBD | 0 |
| MW | 392.45 |
| Rotatable Bonds | 3 |
| TPSA | 88.13 |
| LogP | 2.17 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.76 |
| Exact Mass | 392.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Wedelia prostrata | Asteraceae | Plantae | 318064 |
Showing of synonyms
9alpha-acetyloxy-6beta-isobutoyloxy-1alpha,4alpha-epoxy-eudesm-11(13)-en-5beta,7alpha,8alpha,12-olide
- Farag SF, El-Emary NA, et al. (1996). Eudesmanolides from Wedelia prostrata. Chemical and Pharmaceutical Bulletin,1996,44(4),661-664. [View]
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)CC3C(C2)C4CCC3O4
Level: 0
Mol. Weight: 392.45 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.59
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.68
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.3
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.49
- Plasma Protein Binding
- 63.48
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- 12.0
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.11
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.0
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.14
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -8.46
- Rat (Acute)
- 4.02
- Rat (Chronic Oral)
- 1.72
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 385.59
- Hydration Free Energy
- -5.55
- Log(D) at pH=7.4
- 1.85
- Log(P)
- 2.55
- Log S
- -4.29
- Log(Vapor Pressure)
- -7.33
- Melting Point
- 165.68
- pKa Acid
- 8.36
- pKa Basic
- 3.99
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8096 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8096 |