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1beta-hydroxy-15-oxo-8alpha-(2-(hydroxymethyl)acrolyloyloxy)eudesm-11(13)-en-6alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | O=C[C@@H]1CCC[C@]2(C1[C@H]1OC(=O)C(=C)[C@@H]1[C@H](C2)OC(=O)/C(=C\C)/CO)C |
|---|---|
| InChI | InChI=1S/C20H26O6/c1-4-12(9-21)19(24)25-14-8-20(3)7-5-6-13(10-22)16(20)17-15(14)11(2)18(23)26-17/h4,10,13-17,21H,2,5-9H2,1,3H3/b12-4-/t13-,14-,15+,16?,17-,20+/m0/s1 |
| InChIKey | MYEVWBQFOBSIOC-NGXXMSIOSA-N |
| Formula | C20H26O6 |
| HBA | 6 |
| HBD | 1 |
| MW | 362.42 |
| Rotatable Bonds | 4 |
| TPSA | 89.9 |
| LogP | 1.96 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 362.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cheirolophus x hortigenus | Asteraceae | Plantae | 41544 |
Showing of synonyms
1beta-hydroxy-15-oxo-8alpha-(2-(hydroxymethyl)acrolyloyloxy)eudesm-11(13)-en-6alpha,12-olide
- Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)C3C(CC2)CCCC3
Level: 0
Mol. Weight: 362.42 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.6
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.650
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.92
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.530
- Plasma Protein Binding
- 51.33
- 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
- 8.190
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.800
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.350
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.930
- Micronucleos
- Safe
- 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
- -5.700
- Rat (Acute)
- 4.500
- Rat (Chronic Oral)
- 1.680
- Fathead Minnow
- 3.920
- 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
- 385.260
- Hydration Free Energy
- -7.070
- Log(D) at pH=7.4
- 2.160
- Log(P)
- 1.37
- Log S
- -3.7
- Log(Vapor Pressure)
- -7.52
- Melting Point
- 142.31
- pKa Acid
- 7.28
- pKa Basic
- 4.79
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7962 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7962 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7891 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7891 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7523 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7523 |
| Peroxisome proliferator-activated receptor alpha | Q07869 | PPARA_HUMAN | Homo sapiens | 3 | 0.7341 |
| Peroxisome proliferator-activated receptor alpha | Q07869 | PPARA_HUMAN | Homo sapiens | 3 | 0.7341 |