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4-epi-malacitanolide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene
| Canonical Smiles | OC[C@@H](C(=C)C(=O)O[C@H]1C[C@@]2(C)[C@H](O)CC[C@H]([C@@H]2[C@@H]2[C@@H]1C(=C)C(=O)O2)C=O)O |
|---|---|
| InChI | InChI=1S/C20H26O8/c1-9(12(23)8-22)18(25)27-13-6-20(3)14(24)5-4-11(7-21)16(20)17-15(13)10(2)19(26)28-17/h7,11-17,22-24H,1-2,4-6,8H2,3H3/t11-,12-,13-,14+,15+,16+,17-,20-/m0/s1 |
| InChIKey | OZJAAHIGUMFSHY-SQFWDQPPSA-N |
| Formula | C20H26O8 |
| HBA | 8 |
| HBD | 3 |
| MW | 394.42 |
| Rotatable Bonds | 5 |
| TPSA | 130.36 |
| LogP | -0.1 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 394.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Centaurea papposa | Asteraceae | Plantae | 1006337 |
Showing of synonyms
4-epi-malacitanolide
((3aR,4S,5aR,6R,9R,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo(g)(1)benzofuran-4-yl) (3R)-3,4-dihydroxy-2-methylidenebutanoate
[(3aR,4S,5aR,6R,9R,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate
CHEMBL517009
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)C3C(CC2)CCCC3
Level: 0
Mol. Weight: 394.42 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
- -4.78
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.19
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.48
- Plasma Protein Binding
- 48.48
- 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
- 6.26
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.08
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.34
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.08
- 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
- -9.92
- Rat (Acute)
- 4.93
- Rat (Chronic Oral)
- 1.99
- Fathead Minnow
- 4.01
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 430.39
- Hydration Free Energy
- -9.59
- Log(D) at pH=7.4
- 0.77
- Log(P)
- -0.67
- Log S
- -2.22
- Log(Vapor Pressure)
- -9.72
- Melting Point
- 164.36
- pKa Acid
- 5.56
- pKa Basic
- 5.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7175 |