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8alpha-isobutanoyloxy-1alpha,4alpha,10alpha-trihydroxy-2beta,3beta-epoxy-11,13-dehydroguaia-6alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O=C(C(C)C)O[C@H]1C[C@@](C)(O)[C@]2([C@@H]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)[C@]([C@@H]1[C@H]2O1)(C)O)O |
|---|---|
| InChI | InChI=1S/C19H28O8/c1-7(2)15(20)25-9-6-17(4,22)19(24)12(18(5,23)13-14(19)27-13)11-10(9)8(3)16(21)26-11/h7-14,22-24H,6H2,1-5H3/t8-,9-,10+,11-,12-,13-,14+,17+,18-,19+/m0/s1 |
| InChIKey | HHKPUDQKGQCHRO-ZTXZPJQQSA-N |
| Formula | C19H28O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 384.43 |
| Rotatable Bonds | 2 |
| TPSA | 125.82 |
| LogP | -0.23 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.89 |
| Exact Mass | 384.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Otanthus maritimus | Asteraceae | Plantae | 1155244 |
Showing of synonyms
8alpha-isobutanoyloxy-1alpha,4alpha,10alpha-trihydroxy-2beta,3beta-epoxy-11,13-dehydroguaia-6alpha,12-olide
- Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
No compound-protein relationship available.
SMILES: C12C(O2)CC3C1CCCC4C3OC(=O)C4
Level: 0
Mol. Weight: 384.43 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.18
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.770
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.330
- Plasma Protein Binding
- 36.59
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.070
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.190
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.360
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.730
- 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
- -7.150
- Rat (Acute)
- 4.610
- Rat (Chronic Oral)
- 2.260
- Fathead Minnow
- 3.780
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 392.460
- Hydration Free Energy
- -9.120
- Log(D) at pH=7.4
- -0.310
- Log(P)
- 0.33
- Log S
- -2.28
- Log(Vapor Pressure)
- -8.43
- Melting Point
- 165.13
- pKa Acid
- 5.44
- pKa Basic
- 3.11