Select a section from the left sidebar
Khayanolide B
- Family: Plantae - Meliaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Limonoid
| Canonical Smiles | COC(=O)[C@H]([C@H]1[C@@]2(C)C[C@]3([C@]1(C)C1CC[C@@]4([C@@]5([C@]1([C@H]3[C@H]([C@H]2O)O5)O)CC(=O)O[C@H]4c1ccoc1)C)O)O |
|---|---|
| InChI | InChI=1S/C27H34O10/c1-22-11-25(32)18-16(19(22)30)37-26-9-14(28)36-20(12-6-8-35-10-12)23(26,2)7-5-13(27(18,26)33)24(25,3)17(22)15(29)21(31)34-4/h6,8,10,13,15-20,29-30,32-33H,5,7,9,11H2,1-4H3/t13?,15-,16+,17-,18-,19+,20-,22+,23-,24+,25-,26+,27-/m0/s1 |
| InChIKey | ZDYKUDUSNJTTKV-FKVNRSASSA-N |
| Formula | C27H34O10 |
| HBA | 10 |
| HBD | 4 |
| MW | 518.56 |
| Rotatable Bonds | 3 |
| TPSA | 155.89 |
| LogP | 0.85 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 37 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.78 |
| Exact Mass | 518.22 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Khaya senegalensis | Meliaceae | Plantae | 587579 |
| 2 | Khaya senegalensis | Meliaceae | Plantae | 587579 |
| 3 | Khaya senegalensis | Meliaceae | Plantae | 587579 |
Showing of synonyms
Khayanolide B
- 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]
- Nakatani M, Abdelgaleil SAM, et al. (2000). Khayanolides A and B, new rearranged phragmalin limonoid antifeedants from Khaya senegalensis. Tetrahedron Letters,2000,41(33),6473-6477. [View]
- Abdelgaleil SAM, Okamura H, et al. (2001). Khayanolides, rearranged phragmalin limonoid antifeedants from Khaya senegalensis. Tetrahedron,2001,57(1),119-126. [View]
Pubchem:
101069233
No compound-protein relationship available.
SMILES: c1occc1C(OC(=O)C2)C3CCC4C(C5C6C4C237)CC(C5)CC6O7
Level: 1
Mol. Weight: 518.56 g/mol
SMILES: O1C2CC(C3)CC(C3C2C4C156)C4CCC5COC(=O)C6
Level: 0
Mol. Weight: 518.56 g/mol
SMILES: c1ccoc1
Level: 0
Mol. Weight: 518.56 g/mol
Antifeedant
Antiviral
Absorption
- Caco-2 (logPapp)
- -5.96
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.020
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -0.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.610
- Plasma Protein Binding
- 80.94
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.610
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.200
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.470
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.450
- 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
- -1338.280
- Rat (Acute)
- 4.680
- Rat (Chronic Oral)
- 3.390
- Fathead Minnow
- 2.580
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 451.950
- Hydration Free Energy
- -2.930
- Log(D) at pH=7.4
- 1.610
- Log(P)
- 1.01
- Log S
- -2.97
- Log(Vapor Pressure)
- -11.22
- Melting Point
- 233.82
- pKa Acid
- 5.16
- pKa Basic
- 4.99
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7782 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7782 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7655 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7655 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7625 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7625 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7051 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7051 |