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3-O-detigloyl-3-O-acetylswietenine
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | COC(=O)[C@@H]1[C@@H]2C=C3[C@@H]4CC(=O)O[C@H]([C@]4(C)CC[C@@H]3[C@@](C2=O)([C@H](C1(C)C)[C@H](C(=O)OC)O)C)c1cocc1 |
|---|---|
| InChI | InChI=1S/C29H36O9/c1-27(2)20(25(33)35-5)16-11-15-17(29(4,23(16)32)22(27)21(31)26(34)36-6)7-9-28(3)18(15)12-19(30)38-24(28)14-8-10-37-13-14/h8,10-11,13,16-18,20-22,24,31H,7,9,12H2,1-6H3/t16-,17-,18-,20-,21+,22-,24-,28+,29+/m0/s1 |
| InChIKey | WDAIBJQDOHLLQK-ZXTUPGKLSA-N |
| Formula | C29H36O9 |
| HBA | 9 |
| HBD | 1 |
| MW | 528.6 |
| Rotatable Bonds | 4 |
| TPSA | 129.34 |
| LogP | 3.41 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.66 |
| Exact Mass | 528.24 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Khaya ivorensis | Meliaceae | Plantae | 486173 |
Showing of synonyms
3-O-detigloyl-3-O-acetylswietenine
- Abdelgaleil S, El-Aswad AF (2005). Antifeedant and Growth Inhibitory Effects of Tetranortriterpenoids Isolated from Three Meliaceous Species on the Cotton Leafworm, Spodoptera littoralis (Boisd.). Journal of Applied Sciences Research, 2005, 1(2). [View]
Pubchem:
101371879
No compound-protein relationship available.
SMILES: c1occc1C2OC(=O)CC3C2CCC(C3=4)C5C(=O)C(C4)CCC5
Level: 1
Mol. Weight: 528.6 g/mol
SMILES: C1CCC(C2)C(=O)C1C(C=23)CCC4C3CC(=O)OC4
Level: 0
Mol. Weight: 528.6 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 528.6 g/mol
Antifeedant
Absorption
- Caco-2 (logPapp)
- -5.05
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.840
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.47
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.080
- Plasma Protein Binding
- 81.23
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 10.460
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.270
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.040
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.890
- 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
- -1448.460
- Rat (Acute)
- 4.400
- Rat (Chronic Oral)
- 2.610
- Fathead Minnow
- 7.420
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 471.030
- Hydration Free Energy
- -2.810
- Log(D) at pH=7.4
- 3.520
- Log(P)
- 2.78
- Log S
- -5.2
- Log(Vapor Pressure)
- -9.81
- Melting Point
- 256.11
- pKa Acid
- 6.71
- pKa Basic
- 3.07
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7703 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7582 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7557 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7449 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7281 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7242 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7215 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7205 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7175 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7161 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7118 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7017 |