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6alpha-acetoxy-1alpha-hydroxyguaia-4(15),10(14),11(13)-trien-8alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CC(=O)O[C@H]1[C@H]2[C@@H](OC(=O)C2=C)CC(=C)[C@]2([C@H]1C(=C)CC2)O |
|---|---|
| InChI | InChI=1S/C17H20O5/c1-8-5-6-17(20)9(2)7-12-13(10(3)16(19)22-12)15(14(8)17)21-11(4)18/h12-15,20H,1-3,5-7H2,4H3/t12-,13+,14-,15-,17+/m0/s1 |
| InChIKey | GYRJPATVNGOBRW-CEEVZKBLSA-N |
| Formula | C17H20O5 |
| HBA | 5 |
| HBD | 1 |
| MW | 304.34 |
| Rotatable Bonds | 1 |
| TPSA | 72.83 |
| LogP | 1.67 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 304.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Brocchia cinerea | Asteraceae | Plantae | 282208 |
Showing of synonyms
6alpha-acetoxy-1alpha-hydroxyguaia-4(15),10(14),11(13)-trien-8alpha,12-olide
- Jakupovic J, Aal MA, et al. (1988). Further glaucolides and other sesquiterpene lactones from Brocchia cinerea.. Phytochemistry,1988,27(7),2219-2224. [View]
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)CC(=C)C3C(C2)C(=C)CC3
Level: 0
Mol. Weight: 304.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.6
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.51
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.45
- Plasma Protein Binding
- 46.42
- 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
- 9.81
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.03
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.12
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.75
- 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
- -0.39
- Rat (Acute)
- 3.4
- Rat (Chronic Oral)
- 1.82
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 337.02
- Hydration Free Energy
- -6.88
- Log(D) at pH=7.4
- 0.92
- Log(P)
- 0.92
- Log S
- -2.85
- Log(Vapor Pressure)
- -6.69
- Melting Point
- 153.16
- pKa Acid
- 6.85
- pKa Basic
- 4.72
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8649 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8649 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7578 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7578 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7367 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7367 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7367 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7367 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7165 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7165 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7144 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7144 |