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1alpha,4alpha,10alpha-trihydroxy-8alpha-valeryloxy-11,13-dehydroguaia-2-en-6alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CC(CC(=O)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=C2)(C)O)O)C |
|---|---|
| InChI | InChI=1S/C20H30O7/c1-10(2)8-13(21)26-12-9-19(5,24)20(25)7-6-18(4,23)16(20)15-14(12)11(3)17(22)27-15/h6-7,10-12,14-16,23-25H,8-9H2,1-5H3/t11-,12-,14+,15-,16-,18+,19+,20-/m0/s1 |
| InChIKey | QDEBNXLKVXHODZ-MLBSSZIMSA-N |
| Formula | C20H30O7 |
| HBA | 7 |
| HBD | 3 |
| MW | 382.45 |
| Rotatable Bonds | 3 |
| TPSA | 113.29 |
| LogP | 0.94 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 382.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Otanthus maritimus | Asteraceae | Plantae | 1155244 |
Showing of synonyms
1alpha,4alpha,10alpha-trihydroxy-8alpha-valeryloxy-11,13-dehydroguaia-2-en-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: C1C(=O)OC2C1CCCC(C23)C=CC3
Level: 0
Mol. Weight: 382.45 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.57
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.76
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.78
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.52
- Plasma Protein Binding
- 56.29
- 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
- 6.6
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.41
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.59
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.89
- 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
- -4.78
- Rat (Acute)
- 3.85
- Rat (Chronic Oral)
- 2.21
- Fathead Minnow
- 3.97
- 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
- 386.92
- Hydration Free Energy
- -9.33
- Log(D) at pH=7.4
- 1.22
- Log(P)
- 0.85
- Log S
- -2.73
- Log(Vapor Pressure)
- -7.8
- Melting Point
- 163.06
- pKa Acid
- 6.44
- pKa Basic
- 5.33