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1beta,8beta-dihydroxyeudesman-3,7(11)-dien-8alpha,12-olide
- Family: Plantae - Apiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O=C1O[C@@]2(C(=C1C)C[C@@H]1[C@](C2)(C)[C@H](O)CC=C1C)O |
|---|---|
| InChI | InChI=1S/C15H20O4/c1-8-4-5-12(16)14(3)7-15(18)11(6-10(8)14)9(2)13(17)19-15/h4,10,12,16,18H,5-7H2,1-3H3/t10-,12+,14+,15-/m0/s1 |
| InChIKey | OHYLFUASNKOIGF-BTQDYEIMSA-N |
| Formula | C15H20O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 264.32 |
| Rotatable Bonds | 0 |
| TPSA | 66.76 |
| LogP | 1.68 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 264.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Smyrnium olusatrum | Apiaceae | Plantae | 40962 |
Showing of synonyms
1beta,8beta-dihydroxyeudesman-3,7(11)-dien-8alpha,12-olide
366494-92-0
(4aS,8R,8aR,9aS)-4a,7,8,8a,9,9a-Hexahydro-8,9a-dihydroxy-3,5,8a-trimethylnaphtho[2,3-b]furan-2(4H)-one
(4aS,8R,8aR,9aS)-4a,7,8,8a,9,9a-Hexahydro-8,9a-dihydroxy-3,5,8a-trimethylnaphtho(2,3-b)furan-2(4H)-one
DTXSID101112699
- El-Gamal AA (2001). Sesquiterpene lactones from Smyrnium olusatrum. Phytochemistry,2001,57(8),1197-1200. [View]
No compound-protein relationship available.
SMILES: C1C(=O)OC(C=12)CC3C(C2)C=CCC3
Level: 0
Mol. Weight: 264.32 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.8
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.38
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.85
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.42
- Plasma Protein Binding
- 38.9
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- 6.56
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.22
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- 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
- 4.87
- Micronucleos
- Safe
- 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
- -1.04
- Rat (Acute)
- 2.47
- Rat (Chronic Oral)
- 1.71
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 325.6
- Hydration Free Energy
- -8.44
- Log(D) at pH=7.4
- 1.42
- Log(P)
- 2.34
- Log S
- -2.32
- Log(Vapor Pressure)
- -6.01
- Melting Point
- 169.37
- pKa Acid
- 6.7
- pKa Basic
- 5.23
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8360 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8360 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7989 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7989 |