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8alpha-(3,4-dihydroxy-2-methylenebutanoyloxy)dehydromelitensin
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | OCC(=C)C1[C@H]2OC(=O)C(=C)[C@@H]2[C@H](C[C@@]1(C)C=C)OC(=O)C(=C)[C@@H](CO)O |
|---|---|
| InChI | InChI=1S/C20H26O7/c1-6-20(5)7-14(26-18(24)11(3)13(23)9-22)15-12(4)19(25)27-17(15)16(20)10(2)8-21/h6,13-17,21-23H,1-4,7-9H2,5H3/t13-,14+,15-,16?,17+,20-/m1/s1 |
| InChIKey | KUOSLPBZDWVFER-WFFLBGQYSA-N |
| Formula | C20H26O7 |
| HBA | 7 |
| HBD | 3 |
| MW | 378.42 |
| Rotatable Bonds | 7 |
| TPSA | 113.29 |
| LogP | 0.67 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.5 |
| Exact Mass | 378.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Centaurea tougourensis | Asteraceae | Plantae | 1486586 |
Showing of synonyms
8alpha-(3,4-dihydroxy-2-methylenebutanoyloxy)dehydromelitensin
- Nacer A, Merza J, et al. (2012). Sesquiterpene lactones from Centaurea tougourensis. Biochemical Systematics and Ecology,2012,43,163-165. [View]
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)CCCC2
Level: 0
Mol. Weight: 378.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.69
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.71
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.56
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.57
- Plasma Protein Binding
- 60.81
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.51
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.07
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.02
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.27
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -5.34
- Rat (Acute)
- 3.75
- Rat (Chronic Oral)
- 2.67
- Fathead Minnow
- 3.99
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 395.71
- Hydration Free Energy
- -9.17
- Log(D) at pH=7.4
- 1.24
- Log(P)
- 0.67
- Log S
- -2.65
- Log(Vapor Pressure)
- -8.92
- Melting Point
- 124.14
- pKa Acid
- 6.24
- pKa Basic
- 4.13
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8860 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8860 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8549 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8549 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8260 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8260 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8003 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8003 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7536 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7536 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7299 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7299 |