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Seneganolide
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | O=C1O[C@@H](c2ccoc2)[C@]2([C@@H](C1)[C@]13C[C@@H]4[C@](O1)([C@@]1([C@H]3CC2)COC(=O)C[C@H]1C(C4=O)(C)C)O)C |
|---|---|
| InChI | InChI=1S/C26H30O8/c1-22(2)16-8-18(27)32-12-24(16)15-4-6-23(3)17(9-19(28)33-21(23)13-5-7-31-11-13)25(15)10-14(20(22)29)26(24,30)34-25/h5,7,11,14-17,21,30H,4,6,8-10,12H2,1-3H3/t14-,15+,16-,17+,21-,23+,24+,25+,26-/m0/s1 |
| InChIKey | VIOKSDWKSSMHBF-MQELVVIJSA-N |
| Formula | C26H30O8 |
| HBA | 8 |
| HBD | 1 |
| MW | 470.52 |
| Rotatable Bonds | 1 |
| TPSA | 112.27 |
| LogP | 2.94 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 470.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Khaya senegalensis | Meliaceae | Plantae | 587579 |
| 2 | Khaya senegalensis | Meliaceae | Plantae | 587579 |
Showing of synonyms
Seneganolide
301530-12-1
(1S,2R,6R,7R,10R,11S,16S,19S,20S)-6-(furan-3-yl)-20-hydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo[17.2.1.01,10.02,7.011,16.011,20]docosane-4,14,18-trione
(1S,2R,6R,7R,10R,11S,16S,19S,20S)-6-(furan-3-yl)-20-hydroxy-7,17,17-trimethyl-5,13,21-trioxahexacyclo(17.2.1.01,10.02,7.011,16.011,20)docosane-4,14,18-trione
Senegalide
CHEMBL2332203
HY-N1284
AKOS032948196
CS-0016688
- Nakatani M, Abdelgaleil SA, et al. (2001). Antifeedant rings B and D opened limonoids from Khaya senegalensis. Journal of Natural Products,2001,64(10),1261-1265. [View] [PubMed]
- Abdelgaleil SAM, Okamura H, et al. (2001). Khayanolides, rearranged phragmalin limonoid antifeedants from Khaya senegalensis. Tetrahedron,2001,57(1),119-126. [View]
Pubchem:
10695684
Cas:
301530-12-1
Zinc:
ZINC000039183182
Nmrshiftdb2:
70023124
Chembl:
CHEMBL2332203
No compound-protein relationship available.
SMILES: c1occc1C(OC(=O)C2)C(CC3)C2C4(C3C567)CC(C5O4)C(=O)CC6CC(=O)OC7
Level: 1
Mol. Weight: 470.52 g/mol
SMILES: C1C(=O)OCC(CC2)C1C3(C2C456)CC(C4O3)C(=O)CC5CC(=O)OC6
Level: 0
Mol. Weight: 470.52 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 470.52 g/mol
Antifeedant
Antiviral
Absorption
- Caco-2 (logPapp)
- -5.42
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.99
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.67
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.81
- Plasma Protein Binding
- 66.9
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.36
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.06
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.16
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.82
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -423.82
- Rat (Acute)
- 5.17
- Rat (Chronic Oral)
- 2.38
- Fathead Minnow
- 4.01
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 498.08
- Hydration Free Energy
- -2.93
- Log(D) at pH=7.4
- 1.84
- Log(P)
- 1.79
- Log S
- -5.32
- Log(Vapor Pressure)
- -10.41
- Melting Point
- 308.67
- pKa Acid
- 5.28
- pKa Basic
- 4.26
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7713 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7713 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7346 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7346 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7312 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7312 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7279 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7279 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 3 | 0.7034 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 3 | 0.7034 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7014 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 2 | 0.7014 |