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1beta,10alpha,4alpha,5beta-diepoxy-6beta-hydroxyglechoman-8alpha,12-olide
- Family: Apiaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O[C@@H]1C2=C(C)C(=O)O[C@H]2C[C@]2(C)OC2CC[C@@]2(C1O2)C |
|---|---|
| InChI | InChI=1S/C15H20O5/c1-7-10-8(18-13(7)17)6-15(3)9(19-15)4-5-14(2)12(20-14)11(10)16/h8-9,11-12,16H,4-6H2,1-3H3/t8-,9?,11+,12?,14+,15-/m0/s1 |
| InChIKey | BWSYOMVQMMVGIN-GNQGMBEFSA-N |
| Formula | C15H20O5 |
| HBA | 5 |
| HBD | 1 |
| MW | 280.32 |
| Rotatable Bonds | 0 |
| TPSA | 71.59 |
| LogP | 1.09 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 280.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Smyrnium olusatrum | Apiaceae | Plantae | 40962 |
Showing of synonyms
1beta,10alpha,4alpha,5beta-diepoxy-6beta-hydroxyglechoman-8alpha,12-olide
- El-Gamal AA (2001). Sesquiterpene lactones from Smyrnium olusatrum. Phytochemistry,2001,57(8),1197-1200. [View]
No compound-protein relationship available.
SMILES: C12C(O2)CCC3C(O3)CC4C(C1)=CC(=O)O4
Level: 0
Mol. Weight: 222.24 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.0
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.49
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.86
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.09
- Plasma Protein Binding
- 4.35
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 14.12
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.27
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- -0.44
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.7
- 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
- -3.62
- Rat (Acute)
- 2.65
- Rat (Chronic Oral)
- 1.36
- Fathead Minnow
- 3.77
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 353.54
- Hydration Free Energy
- -7.2
- Log(D) at pH=7.4
- 0.44
- Log(P)
- 0.51
- Log S
- -1.35
- Log(Vapor Pressure)
- -5.16
- Melting Point
- 90.2
- pKa Acid
- 5.29
- pKa Basic
- 2.33
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7806 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7806 |
| Ferric enterobactin-binding periplasmic protein FepB | P0AEL6 | FEPB_ECOLI | Escherichia coli | 3 | 0.7716 |
| Ferric enterobactin-binding periplasmic protein FepB | P0AEL6 | FEPB_ECOLI | Escherichia coli | 3 | 0.7716 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7394 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7394 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7224 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7224 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7150 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7150 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7124 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7124 |