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(6R,7R,8S, 3'R)-8alpha-(3,4-dihydroxy-2-methylene-butanoyloxy)-15-oxohelianga-1(10),4(5),11(13)-trien-6-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | OC[C@H](C(=C)C(=O)O[C@H]1C/C(=C/CC/C(=C\[C@@H]2[C@@H]1C(=C)C(=O)O2)/C=O)/C)O |
|---|---|
| InChI | InChI=1S/C20H24O7/c1-11-5-4-6-14(9-21)8-17-18(13(3)20(25)27-17)16(7-11)26-19(24)12(2)15(23)10-22/h5,8-9,15-18,22-23H,2-4,6-7,10H2,1H3/b11-5+,14-8+/t15-,16+,17-,18-/m1/s1 |
| InChIKey | GCPJCNXGKVLIOY-CATNKTEESA-N |
| Formula | C20H24O7 |
| HBA | 7 |
| HBD | 2 |
| MW | 376.41 |
| Rotatable Bonds | 5 |
| TPSA | 110.13 |
| LogP | 1.16 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.45 |
| Exact Mass | 376.15 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Centaurea tougourensis | Asteraceae | Plantae | 1486586 |
Showing of synonyms
(6R,7R,8S, 3'R)-8alpha-(3,4-dihydroxy-2-methylene-butanoyloxy)-15-oxohelianga-1(10),4(5),11(13)-trien-6-olide
- 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)C=CCCC=CCC2
Level: 0
Mol. Weight: 376.41 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.91
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.66
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.33
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.51
- Plasma Protein Binding
- 45.19
- 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
- 6.06
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.52
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.74
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 6.82
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Toxic
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -3.38
- Rat (Acute)
- 4.69
- Rat (Chronic Oral)
- 1.98
- Fathead Minnow
- 4.47
- 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
- 416.26
- Hydration Free Energy
- -9.09
- Log(D) at pH=7.4
- 1.34
- Log(P)
- 1.19
- Log S
- -2.46
- Log(Vapor Pressure)
- -8.55
- Melting Point
- 130.87
- pKa Acid
- 5.76
- pKa Basic
- 4.3
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8034 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.8034 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7829 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7829 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7704 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7704 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7353 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 2 | 0.7353 |
| 14-3-3 protein gamma | P61981 | 1433G_HUMAN | Homo sapiens | 3 | 0.7352 |
| 14-3-3 protein gamma | P61981 | 1433G_HUMAN | Homo sapiens | 3 | 0.7352 |
| ATP-dependent Clp protease proteolytic subunit | P56156 | CLPP_HELPY | Helicobacter pylori | 4 | 0.7101 |
| ATP-dependent Clp protease proteolytic subunit | P56156 | CLPP_HELPY | Helicobacter pylori | 4 | 0.7101 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7057 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7057 |