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3beta-O-(2-methylbutyryl)-moroccolide A
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CCC(C(=O)O[C@H]1[C@@H]2O[C@@]1(C)[C@H]1C2=C(C)CC[C@@H]2[C@H]1OC(=O)C2=C)C |
|---|---|
| InChI | InChI=1S/C20H26O5/c1-6-9(2)18(21)24-17-16-13-10(3)7-8-12-11(4)19(22)23-15(12)14(13)20(17,5)25-16/h9,12,14-17H,4,6-8H2,1-3,5H3/t9?,12-,14-,15+,16+,17-,20-/m0/s1 |
| InChIKey | FPLUWNGZVAMKNR-BTAUDAJJSA-N |
| Formula | C20H26O5 |
| HBA | 5 |
| HBD | 0 |
| MW | 346.42 |
| Rotatable Bonds | 3 |
| TPSA | 61.83 |
| LogP | 2.94 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 346.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Warionia saharae | Asteraceae | Plantae | 40727 |
| 2 | Warionia saharae | Asteraceae | Plantae | 40727 |
Showing of synonyms
3beta-O-(2-methylbutyryl)-moroccolide A
3BETA-O-(2-METHYLBUTYRYL)MOROCCOLIDE A
((1S,2S,3R,7S,12R,14S)-1,10-dimethyl-6-methylidene-5-oxo-4,13-dioxatetracyclo(10.1.1.02,11.03,7)tetradec-10-en-14-yl) 2-methylbutanoate
[(1S,2S,3R,7S,12R,14S)-1,10-dimethyl-6-methylidene-5-oxo-4,13-dioxatetracyclo[10.1.1.02,11.03,7]tetradec-10-en-14-yl] 2-methylbutanoate
CHEMBL518210
- Hilmi F, Gertsch J, et al. (2003). Cytotoxic versus anti-inflammatory effects in HeLa, Jurkat T and human peripheral blood cells caused by guaianolide-type sesquiterpene lactones. Bioorganic and Medicinal Chemistry,2003,11,3659-3663. [View] [PubMed]
- Hilmi F, Sticher O, et al. (2002). New cytotoxic 6,7-cis and 6,7-trans configured guaianolides from Warionia saharae. Journal of Natural Products,2002,65,523-526. [View] [PubMed]
No compound-protein relationship available.
SMILES: C1CCC(C(=C)C(=O)O2)C2C(C(O3)C4)C=1C34
Level: 0
Mol. Weight: 346.42 g/mol
Anti-inflammatory
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.7
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.72
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.99
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.71
- Plasma Protein Binding
- 55.43
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 12.75
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.21
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.79
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.34
- Micronucleos
- Toxic
- 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
- -0.61
- Rat (Acute)
- 3.31
- Rat (Chronic Oral)
- 2.06
- Fathead Minnow
- 3.92
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 376.28
- Hydration Free Energy
- -4.2
- Log(D) at pH=7.4
- 2.71
- Log(P)
- 3.54
- Log S
- -4.39
- Log(Vapor Pressure)
- -6.73
- Melting Point
- 115.21
- pKa Acid
- 8.83
- pKa Basic
- 5.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7961 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7961 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7747 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7747 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7423 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7423 |
| FKBP-type peptidyl-prolyl cis-trans isomerase FkpA | P45523 | FKBA_ECOLI | Escherichia coli | 4 | 0.7205 |
| FKBP-type peptidyl-prolyl cis-trans isomerase FkpA | P45523 | FKBA_ECOLI | Escherichia coli | 4 | 0.7205 |